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The Ultimate 3 Day Key West Itinerary (With a Map of Key West)

Are you planning your ultimate Key West vacation but not sure where to start? Keep reading!

In this 3 Day Key West itinerary , I cover all the details you need to know to plan your dream vacation to Key West . I’ll go over the best areas to stay and different hotel options, the top restaurants to check out, and all the fun activities you need to do!

In my opinion, 3 days is the perfect amount of time to spend in Key West for first-timers. 3 days gives you the opportunity to soak in the atmosphere, explore the main sites, and go on 1-2 excursions if you wish!

So whether you’re a history buff, a nature enthusiast, or simply seeking the perfect beachside retreat, this Key West itinerary is designed to make the most of your time in the Conch Republic!

Note: This post contains affiliate links. If you click an affiliate link or book through an affiliate program, I receive a small commission at no cost to you! 

The Ultimate Key West Itinerary: 3 Days in the Conch Republic

Where to stay in key west.

Before we dive into this Key West itinerary, let’s talk about where to stay in the famous Key West!

Key West is only 4 miles long, so you might be thinking… how many places can there possibly be to stay? The answer is… a lot!

Key West has a few diverse neighborhoods, but the first decision you’ll need to make is whether you prefer the historic charm of Old Town or the modern amenities of New Town. These two areas split Key West down the middle: the eastern half and the western half.

Most people want to stay in Old Town to be near the action, but there are pros and cons to both areas, which I’ll dive into in the next sections!

Staying in Old Town Key West

For those seeking a slice of Key West’s rich history and vibrant atmosphere, Old Town is the ideal choice. This area is known for its charming streets lined with Victorian-style houses, art galleries, and boutique shops.

When staying in Old Town, you’ll be steps away from the iconic sites. You can explore the Hemingway Home and Museum, soak in the vibrant energy of Mallory Square, and party the night away on Duval Street, then walk back to your accommodation!

Here is a list of the top Old Town Key West hotels , but you can also check out your options on the map above! Old Town has tons of vacation rental and B&B options as well as typical hotels!

• Almond Tree Inn (Moderate)
• Ocean Key Resort (Moderate/Luxury)
• Pier House Resort & Spa (Moderate/Luxury)
• Casa Marina Key West (Luxury)

If you’re staying in Old Town, I recommend skipping the rental car . You’ll be able to access everything you need via walking or biking. Parking in Old Town can be difficult and expensive, so it’s better not to have a car!

However, if you plan to visit other Keys during your stay, you’ll definitely need a car! I recommend doing an epic road trip from Key Largo to Key Wes t so you can experience all the Keys have to offer!

Staying in New Town Key West

If you’re driving into the Keys, New Town is the first area you’ll come across. It’s where the airport is located, along with most of the “chain” hotels. This area is characterized by wider streets, modern conveniences, and a quieter ambiance compared to the lively energy of Old Town.

New Town provides a more relaxed environment, making it an excellent choice for those looking to unwind after a day of exploration. It’s also convenient for those who prefer to have modern amenities at their fingertips.

Hotels in New Town also tend to be a bit cheaper than those in Old Town!

Even though it’s a bit further away from the main Key West attractions, you still may not need a car if you’re staying in New Town.

This is because most of the hotels in New Town have free shuttles to Old Town that run multiple times a day. These shuttles make it easy to visit Old Town without having to worry about parking, or drinking and driving!

Here is a list of the top hotels to check out in New Town Key West!

• Havana Cabana at Key West (Budget/Moderate)
• Parrot Key Hotel & Villas (Moderate)
• Margaritaville Beach House (Moderate)
• The Perry Hotel and Marina (Moderate)
• Hilton Garden Inn (Moderate)

How to Get to Key West

If you’re planning a Key West vacation, you’re going to need to know how to get there! There are a couple of options when it comes to traveling to Key West.

The Key West International Airport (EWY) is extremely convenient to fly into. It’s located right in the heart of New Town and just minutes away from Old Town. If you have the option, I highly recommend flying into Key West.

However, you may find that flights into EWY can be a little pricey. While there are direct flights from around the country, it is still a small airport, which tends to mean higher prices. Airlines like Silver and Allegiant often have cheap, direct flights though, so check to see if they fly out of your home airport!

The other option is to of course: drive! If flight prices into Key West Airport are too high, you can look into Miami Airport (MIA) or Fort Lauderdale Airport (FLL) and then make the drive down to Key West.

I touch more on this in my Ultimate Florida Keys Travel Guide , but I highly recommend this route so you can experience ALL of the Keys, not just Key West. The best option is to fly into Miami, rent a car, and make the drive from Miami to Key West .

Once you arrive in Key West, you can drop off your rental car and fly out of the Key West airport, so you don’t have to drive the length of the Keys twice!

🚗 P.S. I love using RentalCars.com to compare pricing across multiple companies! Plus, they have a great 48-hour cancellation policy!

Key West Map

Lastly, before we get into this Key West itinerary, here is a detailed map of Key West! It includes all of the restaurants, bars, and landmarks mentioned in this itinerary, plus more!

Make sure to save this map of Key West to your own Google Maps so you can access it during your trip!

Day 1: Brunch, Historic Sites & a Sunset Celebration

Blue heaven + exploring old town.

Today is your first full day in Key West! Welcome to paradise!

Start your morning by heading straight to Blue Heaven , one of the most popular restaurants. They open at 8am , and I recommend getting there as close to opening as possible. If you show up later in the morning, be prepared to wait!

I highly recommend getting the Lobster Eggs Benedict and a slice of their GIANT Key Lime Pie!

After breakfast, it’s time to walk around Old Town Key West and explore the historic sites. There are a ton of things to do in the area, so you can choose a few (or all!) of them to fill your morning. Here are a few options!

• Climb to the top of the Key West Lighthouse
• Snap a picture at the Southernmost Point
• Tour Ernest Hemingway’s Home & Museum
• Explore the Key West Butterfly and Nature Conservatory

There are also some great lunch spots around this area, including The Lobster Shack , the Seaside Cafe at the Mansion , and Louie’s Backyard !

Beach Relaxation & Sunset Views

In the afternoon, head over to Fort Zachary Taylor State Park , a 19th-century fort and park located on the southern edge of Key West. Starting at $4.50 per person, the park is a great place to spend an afternoon.

There is a beautiful beach within the park where you can swim, lounge, and even snorkel ! Plus, you can explore the fort’s grounds and learn about the incredible Civil War history.

To finish off your day, make your way to Mallory Square and witness the famous Sunset Celebration . This is the most famous place to watch the sunset in Key West, so if you want a front-row seat, arrive early!

Around sunset, Mallory Square comes alive with food vendors, street performers, music, and more. It’s the perfect way to finish off your first night in Key West.

Day 2: Ocean Adventures & Duval Street

A morning ocean adventure.

On Day 2 of this Key West itinerary, it’s time to get out on the water. You have a couple of options!

If you’re feeling adventurous, I highly recommend visiting Fort Jefferson at Dry Tortugas National Park. a former military installation approximately 60 miles west of Key West in the middle of the ocean.

To get here, you either need to take the 3-hour Yankee Freedom ferry or book a seaplane . (The latter is very pricey!!). Both options book up pretty far in advance, so I recommend looking at your options as soon as possible! You can read more about visiting here .

Fort Jefferson is one of the coolest places I’ve ever visited! The fort was never finished, but it was used during the Civil War and even held prisoners.

You can spend the day walking around the fort and enjoying the scenery. Plus there are incredible beaches and clear water surrounding the fort that you can snorkel and swim in. You can even camp here if you’re into that!!

If Fort Jefferson doesn’t sound like your cup of tea, there are plenty of other ocean adventures to be had locally in Key West. My top recommendation is jet skiing around Key West !! However, if you aren’t visiting the Upper Keys on this trip, going on a reef snorkel & sail adventure is a great option!

Make sure to grab breakfast at the Cuban Coffee Queen before your adventure!

A Night on Duval Street

In the evening, head back down to Old Town and grab dinner at one of the fabulous restaurants nearby. If you want to be on the water, I highly recommend Hot Tin Roof at the Ocean Key Resort. This is a great spot if you can’t get enough of those Key West sunset views! You can also grab pre-dinner drinks at Sunset Pier!

There are also some incredible restaurant options along Duval Street, including Blackfin Bistro , Kaya Island Eats , and Nine One Five .

After dinner, it’s time to check out the famous nightlife in the area and maybe do the “Duval Crawl”. This is the nickname for bar-hopping along Duval Street, as you will be crawling by the end!

➡️ Read Next: Should You Visit Key West in December? Yes! Here’s Why

Some of the most famous bars on Duval include Hog’s Breath Saloon, Sloppy Joe’s, the Bull and Whistle Bar, and the Smokin’ Tuna Saloon.

If dive bars aren’t your thing, don’t worry! There are other nighttime options on Duval Street. You can grab an incredible, adult-friendly dessert at the legendary Better Than Sex restaurant. Another option is to see a drag show at Aqua Nightclub or La Te Da ! Or you can just wander down the street and appreciate the chaos.

Day 3: Bikes, Beach, & a Sunset Cruise

Biking to the beach.

On the last day of this Key West itinerary, start your morning by renting bikes and exploring the south side of Key West. There are plenty of places to rent bikes from, but I highly recommend Eaton Bikes ! They will even drop off the bikes at your hotel for you.

Key West is extremely bike-friendly, so don’t worry about following a particular route, just make your way towards Smathers Beach. There’s a beautiful bike and walking path along A1A in front of the beach you can check out!

Once you’re ready to rest, head onto the gorgeous Smathers Beach, one of the only sprawling white-sand beaches in the entire Florida Keys! This man-made beach actually had white sand imported from the Bahamas, and it does not disappoint! It’s one of my favorite free things to do in Key West !

Shopping and Sunset Cruise

In the afternoon, head back down to Old Town and explore any other sites you missed on your first day. Around Mallory Square, there’s the Key West Aquarium, the Truman Little White House, and the Maritime Museum!

It’s also fun to explore Duval Street during the day! There are many great boutiques and souvenir shops to check out. Make sure to stop in Kermit’s Key Lime Pie Shoppe for another slice of Key lime pie!

In the evening, it’s time to close out your last night in Key West by embarking on a sunset cruise! As you already know, the sunsets in Key West are jaw-dropping, and the best way to see them is from the water on a sunset sail.

There are tons of different Key West sunset cruises to choose from, including dinner cruises, open bar cruises, and cruises with a dance floor! They typically last between 2 and 3 hours and will take you around Key West and Sunset Key as the sun sinks into the ocean.

You can check out my complete guide to Key West Sunset Cruises here to compare prices and help pick the perfect one for you!

Final Thoughts

That wraps up my perfect 3 Day Key West itinerary. As you can see, Key West is more than just an island destination; it’s a kaleidoscope of history, culture, and natural beauty that is sure to leave you wanting more!

And 3 days is the perfect amount of time to spend in Key West to be able to see and do it all. If you follow this 3 day itinerary, I guarantee you’ll have an incredible time!

Don’t forget to check out my other Florida Keys blog posts to help plan your epic adventure! 25 Epic Things to Do in Key West Best Time to Visit the Florida Keys Key Largo vs Key West Should You Visit Key West in January? Yes! Here’s Why

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On a budget? Key West on the cheap isn’t easy, but here are tips

By: Author Bonnie Gross

Posted on Last updated: July 22, 2024

A Key West vacation won’t be cheap — no matter how many tips you read or how much you plan.

In 2024, Key West’s average hotel room rate was $348 a night, according to Expedia.com — among the highest in the country.

In addition, restaurant prices have risen, and you can spend lots of money on admissions and tours.

But the reason Key West commands high prices is that it is a special one-of-kind city and it’s a long way from alternative places to lodge. With history going back hundreds of years, well-preserved architectural gems, a funky street life and great outdoors activities in the surrounding waters, it’s a shame to pass up Key West because it is expensive.

It’s not easy, but it is possible to visit Key West on a budget. The key strategies are:

• Go during the off season, roughly June to November. Expedia says late summer rates are the lowest — August averages $300 a night; September at $270 a night. In high season (January to April) expect rates to average from $450 to $575 a night.
• Despite high averages, you can shop around for accommodations and compromise on amenities or location to find lower prices.
• Seek out affordable, casual restaurants. If you want to enjoy a special meal, make it lunch when a splurge will still cost less.
• Take advantage of the many terrific free and inexpensive things to do in Key West.

Finding a budget Key West hotel or B&B

Even in the summer off-season, your first search for basic Key West motels will come up with rooms starting at least $200 a night. I’ve tried several strategies to beat that price – some successful; some not.

I found bargains in the eastern part of Key West, three miles from Old Town. There are a dozen hotels clustered on Roosevelt Boulevard at the entrance to Key West. They share a shuttle service into Old Town, which helps with parking. But be sure you know about the add-on fees — we paid a $10 “resort” fee at a run-down “bargain” motel.

I had better luck finding accommodations in Key West where I compromised on amenities. One of the great charms of Key West is the historic bed and breakfasts in Old Town. 

Most go for $300 to $400 a night. But there are a few quality places where several bedrooms share a common bathroom, and the savings are great.

Americans love their plumbing, but if you can share a little — as frugal travelers do elsewhere in the world — you can stay in Key West’s Old Town at a great B&B.

We stayed at the Key West Bed and Breakfast , 415 William Street, Key West, a turn-of-the-century house decorated with original art, vibrant color and serving a spectacular breakfast of fresh fruits and homemade blueberry coffee cake.

Booking rooms in Key West requires a consumer to be vigilant: Even at historic B&Bs, watch for extra fees.

The historic Curry House B&B where I stayed recently added a $35 a night “cleaning fee” that was not disclosed in advance (or was extremely well hidden.) With that charge, it was no longer a budget option.

“Resort fees” of $50 a night are common, and you often discover them only when checking in, so if you’re on a budget, ask ahead of time. We stayed at the luxurious Perry Hotel in Stock Island, where we booked a super-bargain rate of $180, but then discovered there was a $50 resort fee and a $25 parking fee. It was still a good price, but not what I had budgeted.

Other lower priced alternatives in Old Town guest houses: Eden House  (some rooms at $200 in August), Duval House (as low as $140 for dates in August) La Pensione (as low as $150 in August) and the Garden House (as low as $140 in August.)

Be aware though: These places will be at least $300 a night Janurary to April. For example, Duval House has rooms for $250 in early December. In mid-January; rooms are $400 and up.

The least expensive lodging in Key West would be 10-bunk-beds to a room at Seashell Motel and Key West Hostel. Hostel beds start at $49 per person; bare-bones motel rooms at $125. Reviews are mixed.

Airbnb and VRBO both have many properties in Key West and some appear to beat hotel prices. One of the most intriguing types of listing are houseboats. If you’re considering a houseboat rental , read this advice from Karuna Eberl, co-author of “Key West & the Lower Keys Travel Guide” with a few tips and questions to ask. 

Also, beware of add-on prices that can dramatically increase VRBO and AirBnB prices.

There are some other vacation rental networks that include Key West listings and they are worth browsing. (You can find them by Googling “owner vacation rentals key west.” I can’t vouch for them, having never tried them, but I saw some potentially good values.)

Another alternative for a reasonably priced room is to stay in the Upper or Middle Keys and come to Key West for a day trip .

One nearby place to stay is Parmer’s Resort , 565 Little Torch Key.  It’s 27 miles or 40 minutes outside Key West.  During low season (September through mid-December), rooms start at $127 (plus fees that bring it to $175.) This is a 1950s-vintage Keys-style waterfront resort with pool, water views and breakfast included. Like a lot of Keys properties, Parmer’s used to be more moderately priced, but it’s a good value if you want a resort experience AND a visit to Key West.

A few other inexpensive nearby choices: Sugarloaf Lodge is 17 miles from Key West and offers basic waterfront rooms off-season starting at $140.

Unadorned and very basic roadside motel rooms are $150 off season at Big Pine Key Motel , 30725 Overseas Hwy, Big Pine Key, which is 29 miles from Key West. Looe Key Reef Resort, 25 miles from Key West, caters to divers and offers basic rooms for as little as $155 in the late summer low season.

You can find summer rates that are lower in the motels of Marathon. These are an hour from Key West, but it’s a beautiful drive over the Seven Mile Bridge.

We’ve stayed in some ordinary mom-and-pop motels in Marathon for $135 to $175 – the Blackfin Resort and Marina , 4650 Overseas Highway, and the Kingsail Resort , 7050 Overseas Highway.

These are not memorable; rather, they are just places to sleep while you fill your days with activities.

If you’re a camper, camping is another good way to make your trip inexpensive. Campsites in the Keys are way more expensive compared to other locales (as much as $100 a night for tents), but they still may save you over hotel rooms.

My colleague Bob Rountree has all the details on camping in the Lower Keys here.

In search of budget Key West restaurants

Key West is foodie heaven, with prices to match.  

Finding good buys in restaurants will take some planning: You may not stumble across these places when you get hungry unless you keep a map handy.

One tip for dining in Key West is to make your main evening meal a tasty assemblage of half-price happy hour appetizers.

An especially good place for happy hour is the historic Key West Seaport . The boardwalk along the harbor is one of the best free activities in Key West.

Folks are feeding tarpon from the docks, fishing charters are displaying their catches and all the colorful yachts and historic ships are on display, with flags snapping.

Many harbor restaurants have happy hours, but I can recommend Alonzo’s Oyster Bar , 700 Front St., Key West. All drinks and an extensive selection of appetizers are half price from 5 to 6:30 p.m. and it’s easy to make a meal of it. We sat outside overlooking the harbor in a setting that didn’t compromise on atmosphere.

Beyond the harbor area but still centrally located,  First Flight Island Restaurant and Brewery, 301 Whitehead St., has a great happy hour at the bar and nearby high-tops. First Flight is located in the beautifully restored historic building that was the ticket office for Pan Am in the 1920s when it began air service between Key West and Havana.

From 4 to 6 p.m., happy hour brings cheap drinks and great appetizers at $5 to $7 a dish. We put together a delicious dinner combining beef brisket mac and cheese, Six Hour Confit Chicken Wings and a plate with three kinds of hummus.

After you eat “dinner” at happy hour, head to a vantage point for sunset. Afterwards, you can enjoy a late-night Cuban sandwich, conch fritters or an arepa at a variety of inexpensive, atmospheric Key West eateries where you order food at a counter and eat at a picnic table or bench.

A few good examples:

We had a great Cuban sandwich ($11) at Frita’s Cuban Burger Cafe , 425 Southard St. Frita’s Cuban burger ($10) is unusual and spicy. Seating is in a small outdoor patio or benches at the take-out window.

Near the seport, is the legendary  B.O’s Fish Wagon at 801 Caroline St., Key West.  B.O.’s Fish Wagon is an open-air assemblage of drift wood, recycled sheets of tin and a 1950s Chevy truck apparently held together by bumper stickers. Folks rave about the fish tacos.

Nearby,  Garbo’s Grill at 603 Greene St., Key West, is sort of a permanently stationed food truck. Seating is outdoors on milks crates or coolers. Their mahi tacos and  Kogi Koren Beef Shortribs, however, ensure there is usually a line and a festive atmosphere.

Right on Duval Street is a small treasure :  the Conch Shack , a restaurant no more than 10 feet wide that accepts only cash and serves up fresh, reasonably priced fare. Three conch fritters are $6; a cheeseburger is $9. Seating is on stools at a counter.

For breakfast or lunch, consider this gem:

A budget-friendly but delicious spot for your obligatory key lime pie is the Old Town Bakery . It’s off the beaten path, five blocks east of Duval at Eaton and Grinnell streets. The key lime pie , ranked in the top 10 in the Keys by Miami New Times is $3.75 a slice with fresh in-house whipped cream, whereas other key lime pies on restaurant menus are $7-$10 a slice. There are also a dozen $10 sandwiches, or come for breakfast for $7.25 breakfast burritos or $4 almond croissants. Open 7 a.m. to 3 p.m.

For an air-conditioned restaurant with table service, we can suggest two classic Key West spots:

You can get reasonably priced diner fare at Harpoon Harry’s , 832 Caroline St. One thing that keeps prices down is that this is a cash-only business. It is most popular for breakfast and lunch ($10 to $12 for sandwiches) but there’s a blue-plate specials for $12.95 each night.

As I asked Key West residents for suggestions for budget dining, at least three people recommended the classic Cuban restaurant , El Siboney , 900 Catherine St., Key West. This is a traditional restaurant with table service and bargain prices — $13.95 for three different preparations of pork, $17.95 for grilled mahi or grouper, topping out at $24.75 for a few types of steak. It was all good and service was efficient. There is now an El Siboney on nearby Stock Island too.

For that “special” lunch, we thought booking a table at Latitudes , located on an island off Key West called Sunset Key, was perfect because it includes a boat ride from Key West to the island. It’s perhaps a 10 minute ride, but the Caribbean color of the water was stunning to see from a boat. The tables have spectacular oceanfront views (with indoor and outdoor seating) and the food is excellent. Lunch for two, including tax and tip, was $70. (It looks like a great place for a splurgy breakfast too.)

Free fun is the secret to Key West on the cheap

It’s easy to be entertained on the cheap by Key West: On your first visit, you might spend all day just wandering historic Old Town and joining the nightly street carnival at Mallory Square sunsets.

But there are so many alternatives that Florida Rambler has devoted another whole article to free things to do in Key West .

Planning your trip to the Florida Keys

• Mile marker guide with dozens of stops to help make the most of your drive south.
• Florida Keys wildlife : Places to see animals
• Tiki bars:  Soak up the Keys atmosphere
• 12 great kayak outings in the Keys
• Top 10 pit stops on Overseas Highway
• Best beaches in the Florida Keys

Key West and Lower Keys

• Key West is less crowded (and more enjoyable) when cruise ships are not in town. Check the cruise ship calendar when making your plans.
• Stock Island, Key West’s fishy funky neighbor is a good spot to discover a restaurant
• Free things to do in Key West
• Florida Rambler guide to the Lower Keys
• Bahia Honda State Park : Good beaches & a great bridge
• No Name Pub worth finding on Big Pine Key
• Key West Butterfly Conservatory : A tranquil stop
• Audubon House , a lovely refuge in Key West
• Historic Key West Seaport
• Historic Key West Cemetery  is full of stories
• Fort Zachary Taylor
• Hogfish Grill: Where Key West locals go for fresh fish
• Key West chickens
• National Key Deer refuge
• Key West Tropical Forest and Botanic Garden: It will charm plant lovers

The author, Bonnie Gross, travels with her husband David Blasco, discovering off-the-beaten path places to hike, kayak, bike, swim and explore. Florida Rambler was founded in 2010 by Bonnie and fellow journalist Bob Rountree, two long-time Florida residents who have spent decades exploring the Florida outdoors. Their articles have been published in the Sun Sentinel, the Miami Herald, the Orlando Sentinel, The Guardian and Visit Florida.

Philip Roddy Jr

Wednesday 23rd of January 2019

If you folks want lower room prices in Key West then stop going. If there rooms don't fill up then they're forced to drop their prices.

Dennis Dowhy

Saturday 13th of October 2018

I truly love the keys. It's unfortunate that they have priced themselves out of business. I just switched to cruise ship travel to the Caribbean because it cost is so much cheaper. A night in the keys goes from 200-900+ a cruise is less than 100 up to 1000 but that is a week or much more. Check out cruises vs rental in the keys.

This site uses Akismet to reduce spam. Learn how your comment data is processed .

This post includes affiliate links from which Florida Rambler may earn a modest commission if a purchase is made. This revenue directly supports the creation of original content for your enjoyment.

YOUR KEY WEST EXPERTS!

• Where to Stay

The Perfect 4 Day Key West Itinerary

We spent an amazing 4 days in Key West. Well, any time in Key West is amazing, right? The Kimpton Key West hosted us for a fun time. We explored all of their properties and tried a few new places for dinner. Along the way, I learned a few things I thought I would share about our Key West itinerary.

First off, let’s talk about planning an itinerary… do it, but don’t overdo it. Leave space in the day for random stuff. You are on vacation, after all, not every second of every day needs to be planned. Plan for an island time experience.

Below are affiliate links, which means we will earn a small commission at no extra charge to you. As always, thanks for your support.

Getting to Key West

How do you get to Key West? There are really three ways… by car, by plane and by ferry.

A lot of airlines now offer direct flights into Key West. Or, you can fly into Miami International Airport and experience the Key West Road trip. If you have never done this, I would plan it at least once. Plan to make stops along the way. Check out the Everglades National Park, Key Largo, and other cool spots along the overseas highway. Did you know there are 11 National Parks in Florida? Two can be found in the Keys (the Everglades and the Dry Tortugas)

The Ultimate Road Trip from Miami to Key West

Along the Overseas Highway, you will notice everything is marked by mileage, with Mile Marker Zero being in Key West.

Rather take a ferry? Check out the Key West Express.

So… with the ground rules set… let’s see how to explore Key West, enjoy some downtime, AND have an amazing time in just 4 days.

The Beginning

Ok.. we planned this on purpose, we arrived very early in Key West. This meant we traveled with very little sleep, but that’s ok.

Side note, I booked our plane tickets directly with the airline. So, they set the schedule, departure/arrivals, and time for the layover. BUT, their itinerary only allowed for 25 minutes from touchdown to take off on our layover down. Might work, if you aren’t 10 minutes late leaving …. but, we managed to make the connecting flight, so all good. But, next time, I will ensure we have plenty of time between connections.

We always travel with carry-on only. It just makes the trip that much easier. Plus, for 4 days… you really don’t need that much stuff. Once we land it’s straight to the hotel. For this visit, we headed to Winslow’s Bungalows. This Kimpton property is just amazing.

Winslow’s Bungalows

Located at 725 Truman Ave, you are fairly close to everything. If you get tired of walking you can always take an Uber or the free Duval Loop bus. If you are taking a cab from the airport to the hotel, you may want to let them know it’s the Kimpton on Truman instead of Winslow’s Bungalows. The reason is these properties used to be part of the Historic Key West Inns, but now are part of the Kimpton family.

This property used to be the Chelsea House and Key Lime Inn. Kimpton has combined them into one property now known as Winslow’s Bungalows.

Here’s a bit of quick history about the property…..

• It’s named after the famous painter and summer Key West resident Winslow Homer
• Has 3 pools, an outdoor bar, and vibrant gardens
• 85 guestrooms including 2 deluxe suites and is Kimpton’s largest Key West hotel
• The room designs pay homage to the property’s past owners including an Army officer, an Irish steamboat Captain, and a circus performer
• On the property is Maloney House, where the first mayor of Key West lived. He planted an amazing fruit grove that is still used by the hotel today.
• The property has 3 stand-alone bungalows to accommodate guests wanting a bit more privacy
• The property is very pet friendly. They offer Henry’s dog treats to their dog guests
• If you want to try the famous Key West bagel made by Goldman’s, they are offered at breakfast (they are very very yummy)
• Music is played at the pool bar
• The old Blue Parrot Inn is across the street and is now part of this property. They have 11 rooms and their pool is called the serenity pool because they don’t play music and it offers a zen tranquil feeling

They didn’t have our room ready yet, remember we arrived early (before checkout). But, that was ok. They held our luggage so we could head off to have breakfast and a much needed cocktail to start the vacation off. Our breakfast of choice? Blue Heaven of course.

After breakfast, it was time to head back to the hotel and enjoy a bit of pool time. Best way to cool off and refresh after a day of traveling.

As you can see, our room was, perfect. Winslow’s Bungalows offers great spaces to relax and enjoy Key West. Not too far from the heart of Duval Street, this place offers three pools and an amazing pool bar.

Fully refreshed, we head out to explore. First stop… the Mile Zero sign. No vacation in Key West is complete without a picture in front of the Mile Zero sign.

Needing a place to cool off, we then headed over to the Custom House. This place offers rotating exhibits all about Key West and those who influenced Key West. Always a great stop. Some the coolest and best things can be found in their gift shop.

Now, it’s time for dinner. A favorite stop of ours is Sloppy Joe’s. I know, I know, it can be a bit touristy, but I still love this place. The food is always good, the drinks are poured strong and they offer live music. Who could ask for more?

Speaking of live music, plan a stop at the Smokin’ Tuna, one of the best places in Key West for music. They have an outdoor courtyard that offers shade and cold adult beverages.

Most of the time I suggest sunset celebration at Mallory Square, but this night, we opted for a different perspective. Sunset from the top of Schooner Wharf. This is the perfect place to see the harbor, enjoy a cold beverage and listen to live music.

Today, hubby heads off to enjoy a morning out on the water fishing. Me… well, I do what I love to do while in Key West, I head out for a morning walk. Who doesn’t love a morning walk around Key West? I love to look at the historic homes that are scattered all over this small island. It’s one of the great things about the Island, they have kept the charm and preserved its history.

Historic Walking Tour

When I get back, it’s time for breakfast. I head down this wandering path at Winslow’s and partake in their complimentary breakfast. It’s a basic continental breakfast. It’s served in the bar area. Enjoying my second (and maybe third) cup of coffee, I did a bit of work. Caught up on a few emails, and, worked on this blog post. At the bar, is a great spot to work. I don’t spend too much time working… after all, there is a lot more to see and do before Kevin returns from his fishing trip.

Kevin returned after a successful fishing trip, and we then set out for the next adventure. Kimpton Hotels hosted us for a tour of their Lighthouse property. This place is very cool Across the street from the Hemingway House, it offers a great view of the lighthouse and they have a very nice bar.

Not staying at the Lighthouse? No worries, the bar is open to the public, Plan to stop in and enjoy this place. The bartender is engaging and can mix many amazing cocktails. We had the best time trying the house specialties. We actually couldn’t decide which ones we liked best. It’s ok to like them all, right?

While in Key West, it seems to always be cocktail time. With that in mind, we had time before our dinner reservations and headed over to General Horseplay. This place is known for their cocktails and fun Happy Hour. It’s a great place to start off an evening.

For dinner… we were hosted by Poke in the Rear. Don’t overlook this place. It was, one of the best dinners we had while on Island.

Today we have a quick bite of breakfast and then head out to explore the streets of Key West. Being married to a photographer, I spend a lot of time wandering around. But, I wouldn’t have it any other way. We saw roosters, flowers, palm trees, and stickers. All my favorites.

Grabbed a cold brew from Cuban Coffee Queen and walked around the Historic Seaport.

Heard the band starting to play at Sunset Pier… which means we are stopping to listen and enjoy a cold beverage. Here’s where I would insert the idea of having free time built into your Key West itinerary. If you “had” to be somewhere … you might miss out on an awesome view, cold beverages, and amazing live music.

A few more stops for pictures and then we are heading back to Winslow’s Bungalows. Not only do they have a great pool bar and pool area, but they offered a free tasting of Mutiny rum. It was yummy and the story was just as interesting.

We didn’t have any dinner plans to speak of so we “thought” we would head over to Mallory Square and enjoy sunset and then play it by ear. I think that’s a great way to spend any evening in Key West, at least one night. No particular plans and let the evening unfold.

Well, as we walked by Little Pearl and saw they had two chairs open at the bar… and we hopped on the chance to eat at Little Pearl. This place offers a tasting style menu and is worth every penny if you can get a reservation.

We have a later flight, also planned on purpose, which gives us almost a full day to play in Key West. What is always fun to see is the “guest” ships that dock at Mallory Square. On this day we were able to see the USCGC Eagle. This 295-foot, three-masted barque is used as a training vessel for future officers of the United States Coast Guard. This is also known as “America’s Tall Ship” and is the largest tall ship flying the Stars and Stripes and the only active square-rigger in US service. Very, very cool to see in Key West.

Then it was off to lunch at First Flight. This is the Southernmost microbrewery and they offer a great courtyard seating area and a wonderful menu.

Afterward, we head off to the airport to head home. As per usual, we grab a last vacation cocktail and share a frozen Key Lime pie on a stick (dipped in chocolate).

We tried new places for food and drinks and had plenty of down time to relax. That’s what makes the perfect vacation… a perfect balance.

More…

I get it, we didn’t do much on this trip. But, we had a really good time. If this seems a bit too slow for you, then check out these ideas:

• Take a guided tour – a food tour, a walking tour, a ghost tour ( see our recommendations here )
• Take the ferry (or seaplane ) out to the Dry Tortugas National Park – be sure to book this one in advance as it sells out quickly.
• Head out on the water to snorkel the coral reefs
• Go up the Keys for a day trip and see Bahia Honda State Park, sea turtles, or the Key Deer on Big Pine Key.
• 3 Reasons Smathers Beach is the best
• Visit one of the 18 museums on the island… like the Truman Little White House

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Destination Daydreamer

The Ultimate Itinerary for a Day Trip to Key West

I tend to think that after spending an entire summer living and working in Key West that I should be able to curate the perfect day trip to Key West… and that’s just what I’ve done for you. When I lived and worked on the island I spent each day off exploring as much of Key West as possible and eating as much awesome Key West food as possible. You can read my ultimate Key West bucketlist with seriously almost every single cool thing there is to do on the island (almost 100 things!). However, if you are looking for what to do in Key West for a day, I am here to give you (from all of my experience and research) the perfect one-day itinerary!

check out this post: The Ultimate Key West, Florida Bucket List | 98 Things to Do

*There may be affiliate links in this post.  Read my  privacy/disclosure policy  to learn more.

Best Time of Year to Spend a Day Key West

One of the magical things about visiting Key West is that you can basically go any time of year and have a great experience. That being said, there are a few things to note about the weather and potential crowds at different times of year in the Florida Keys.

Spring and fall generally are the best times to visit Key West for the most moderate weather. You can expect temperatures to be in the 80s F and you will find fewer crowds than in winter. Speaking of winter, you can expect the most crowds in winter and temperatures to drop to the mid-70s F with lows around 65° F.

In the summer you can expect high humidity and temperatures in the 90s F. Speaking from experience, this definitely feels quite toasty. However, if you are willing to bear the heat, you will be rewarded with less crowds (and possibly a little bit or a lot a bit of seaweed along the beaches depending on the year). Hurricane season generally runs from June-November with higher chances of hurricanes forming towards the latter end of that period.

Obviously, hurricanes don’t pass through the Florida Keys every year, but it’s something to be aware of when planning your ideal Florida Keys itinerary. As I said, I have experience with being in Key West for an entire summer, however, I also returned with my husband on a  Florida road trip  end of October/early November and the weather was perfect and it really felt like the perfect time to visit (minus the fact that a hurricane had come through that summer leaving a few things in shambles 😬 but we were happy to support Key West during a hard time).

Related post: 17 Things You Need to Know Before Visiting Key West, Florida

1 day key west itinerary: quick look.

• Morning: Breakfast/Brunch at Blue Heaven
• Go snorkeling at Fort Zachary Taylor Beach
• Afternoon: Eat Lunch at the cute Cuban Coffee Queen shack along the waterfront
• Snap a pic at the iconic ‘Greetings From Key West’ mural
• Stroll/shop along the Key West Historic Seaport
• Taste Key Lime Pie on a stick from Kermit’s Key Lime Shoppe
• Visit the Southernmost Point and Mile Marker Zero
• Evening: Watch the sunset at the Sunset Celebration at Mallory Square
• Eat Dinner on Duval at Amigos Tortilla Bar

*Use this interactive map to see where all the top stops are for a great day in Key West*

Key West Day Trip In-Depth Itinerary

1. breakfast or brunch at blue heaven.

You have probably seen other sites recommend Blue Heaven for a meal and it is definitely for good reason. Eating breakfast or brunch at Blue Heaven is one of my top recommendations for things to do in Key West. Thankfully, breakfast is served until 2:00 pm, so even if you are running late you can most likely catch breakfast!

Blue Heaven is such a cute eatery and it’s a local hotspot. Unfortunately, reservations aren’t available, but when you arrive, be sure to ask for a seat outside in their relaxed open-air area. It really is my favorite place to sit and eat. If you’re lucky, you’ll get to hear some live music and watch the infamous Key West chickens roaming the patio.

View this post on Instagram A post shared by Key West Blue Heaven (@keywestblueheaven)

I recommend ‘Richard’s Very Good Pancakes’ which are huuuge pancakes with chunks of either banana, pineapple, pecans, or blueberries within! If you are feeling up for some Key Lime Pie, Blue Heaven has one of the most unique pies in Key West with a crazy high topping of meringue.

View this post on Instagram A post shared by Blue Heaven (@blueheavenkw)

related post: Ultimate Key West Food Guide | 19 Places You Must Try

2. snorkeling at fort zachary taylor state park.

Fort Zachary Taylor beach is the ultimate hidden gem of Key West. When I worked in Key West for a summer I quickly learned the locals call it Fort Zach and that it’s one of their favorite spots on the island to visit. I returned to Key West with my husband a few years back and even though we only had about 1.5 days on the island, we made sure to snorkel at Fort Zach.

Key West has a lot of beaches, but only one of them is good for snorkeling, and that’s the beach at Fort Zachary Taylor State Park. The only other option for snorkeling (which is also a great option) is to take an excursion to snorkel at the Florida Reef a few miles offshore. However, if you want to stay on the island, Fort Zach beach is amazing.

The beach has two rocky jetties home to many colorful fish plus the water is a lovely blue/green color. You can rent snorkel gear, seats and umbrellas from a stand on the sand and even grab a snack from Cayo Hueso Cafe if you get hungry.

If you have more time, you can also take a self-guided tour of a Civil War Era Fort at the state park and wander the pretty walking trails in the area. Check out my 10 Best Things to do at Fort Zachary Taylor State Park post to learn more!

related post: 10 Best Things to do at Fort Zachary Taylor State Park in Key West Florida

3. lunch at cuban coffee queen.

If you aren’t totally still stuffed from breakfast at Blue Heaven, after snorkeling you’ll want to swing by Cuban Coffee Queen for a yummy drink, Cuban favorites or other sandwhiches and salads. And the best part is, everything is super reasonably priced (which is a huge bonus to find in Key West).

Cuban Coffee Queen has multiple locations on the island, however, my favorite (and in my opinion the cutest) is their original location on Margaret Street near the Key West Historic Seaport. It’s an adorable walk-up stand right near the water and the side of the establishment has the infamous ‘Greetings From Key West’ mural. From here, you’ll be able to walk to enjoy another great area of Key West (more on that below).

4. Snap a Pic at the Iconic ‘Greetings From Key West’ Mural

Be sure to snap a pic at the infamous ‘Greetings From Key West’ mural on the side of Cuban Coffee Queen. Even if you don’t want to stop for food, this is still a great area for a cute pic and a perfect place to start exploring the Key West Historic Seaport.

5. Stroll Through the Key West Historic Seaport

Right near Cuban Coffee Queen and the Key West mural, is the lovely historic seaport. It’s a nice area to go for a relaxed stroll (much quieter than Duval Street). You can get great harbor views of the sailboats and yachts plus even do some shopping and pick up some trinkets or other items to take home as souvenirs.

The cutest road to stroll is the pedestrian-only road called Lazy Way Lane. It has cute, colorful shops, palm trees and lots of islandy trinket shops.

6. Get Key Lime Pie on a Stick at Kermit’s Key Lime Shoppe

Even if you only have one day in Key West, you MUST try Key Lime Pie. One of the quirkiest and yummiest pies to get is the Kermit’s Key Lime Pie, dipped in chocolate served on a stick. Yep, you heard that right, served like a popsicle! If that sounds like a little much to you, you can also buy it on a stick NOT dipped in chocolate, or you can just purchase a traditional slice of pie. However, if you’re only going to try one piece of Key Lime Pie, I definitely recommend Kermit’s Key Lime Shoppe .

They have a few locations in Key West, however, I like the Elizabeth Street location that is right near the Historic Seaport. It’s a super cute yellow and green wooden building and their original location on the island.

View this post on Instagram A post shared by Key West Food Tours® (@keywestfoodtours)

check out this post: 8 Best Places to Try Key Lime Pie in Key West

7. walk and shop on duval street.

Duval Street is the largest main street in Key West known for bars, restaraunts, galleries and tourist shops and one of the most popular things to do during a day in Key West. For a calmer, more family-friendly experience on Duval, you may want to walk and shop Duval Street during the day.

View this post on Instagram A post shared by Key West, FL🌞 (@keywest)

One of my favorite spots is the fanciest Walgreens you’ll ever see (yes… Walgreens). The Walgreens on Duval is stationed in a converted, colorful, vintage building called The Strand Theater. From the outside you would neverrrr guess this beautiful building is currently home to a Walgreens. Another favorite cute spot on Duval is the rainbow crosswalk intersection.

At night, the bars on Duval come alive and the sidewalks are crowded. If the bar scene is your thing, you may consider booking a Duval Street pub crawl to experience some of the island’s most iconic bars like Sloppy Joe’s.

8. Visit the Southernmost Point and Mile Marker Zero

While definitely touristy, making a quick stop at the Southernmost Point and Mile Marker Zero are two classic things to do in Key West in one day. The Southernmost Point marker indicates the Southernmost Point of the Continental United States, from this point you are actually closer to Cuba than Miami! It’s a fun spot that’s mostly a quick photo opportunity.

Mile Marker Zero is similar to the Southernmost Point in that it’s a very quick stop/photo-op. It’s the end of Highway US 1 and just a fun spot to see as you are so far south in the Florida Keys.

Related post: The Ultimate Key West, Florida Bucket List | 98 Things to Do

9. watch the sunset at the sunset celebration at mallory square.

If you are doing Key West in a day, I sure hope you have time to stick around for sunset because the Sunset Celebration at Mallory Square is one of my favorite things about Key West. I have visited the sunset celebration many, many times and it’s always a fun experience.

Beginning about two hours before sunset, right on the water in Mallory Square, you’ll catch the Sunset Celebration every single night of the year. There are local vendors, musicians, stunt performers and more! From here you get to watch the huge ball of sun drop below the horizon and possibly even clap once it’s set! It really is a great time.

If you prefer a quieter and possibly more romantic experience watching the sunset, be sure to check out one of the many awesome sunset sails that Key West offers. You can hop aboard a large catamaran, sailboat or even a small private boat to experience the sunset from the water. I also have done a sunset sail in Key West and it’s another awesome way to experience the sunset that I highly recommend. For other great excursion ideas check out my top Key West excursions guide (they are all worth the price!).

related post: The 7 Most Beautiful Places You Need Watch the Sunset in Key West

10. eat dinner at amigos tortilla bar.

When living in Key West, Amigos was by far the restaraunt I most frequently visited. It’s a super yummy Mexican joint with the option to sit in the open-air facing Duval Street (makes for great people watching). You can buy delicious tacos, burritos or bowls with various veggie and meat options with (of course) Baja fish being a top contender.

Amigos is a great option for a relaxed, yummy dinner on Duval in the heart of Key West. If you are curious about other great places to eat, be sure to check out my Ultimate Key West Food Guide.

And that is the best way to spend your day in Key West! Please let me know if you have any questions about a day trip to Key West from Miami or from anywhere in the Florida Keys!  I’m a real person  that loves to talk travel and I’ll be sure to get back to you!

Check out these other posts, I know you’ll love them:

• Ultimate Key West Food Guide | 19 Places You Must Try
• 17 Things You Need to Know Before Visiting Key West, Florida
• The Ultimate Key West, Florida Bucket List | 98 Things to Do
• 10 Best Things to do at Fort Zachary Taylor State Park in Key West Florida

8 Key West Excursions Definitely Worth the Money

• 8 Best Places to Try Key Lime Pie in Key West
• The 7 Most Beautiful Places You Need Watch the Sunset in Key West
• 5 Reasons You Need to Rent Jet Skis in Key West + How to Rent

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Is this a walkable route or should we rent a golf cart? We will be in KW for a day on a cruise ship. Thanks

Hey Meggan! How fun you’ll be in Key West for a day. I’d say it depends on how comfortable you are with walking and how much time you have in port. the longest walk is only 30 minutes with a couple 20 minute walks in there as well. However, walking is a great way to see the area so I do recommend it if you have time/ability. Otherwise, a golf cart is the next best idea!

Karen Schopp

I would like to go in April. Can you recommend a clean affordable place to stay for 2-3 days ?

Hey Karen! I don’t have many hotel recommendations, however, on the top of my list for next time we visit is The Perry Hotel & Marina Key West which is just barely off Key West on Stock Island which helps with the price a little bit (but they have a shuttle that takes you to Duval Street if needed).

Do you think it’s worth visiting Key West if I can only go for the day via Key West Express? Is that too short of a time? I’ll be visiting Sanibel for a while in late august and was thinking of taking a day trip from Fort Myers. Thank you.

Hey Barb! I hope you have a great time in Florida. It looks like the ferry is about 3.5 hours each way leaving around 4-5 hours to explore Key West in one day. To me that seems like a lot of travel time for not much time in Key West, however, it that sounds okay to you it could be worth it! A great option would be to take the Conch Tour Train to get a tour of the island and see all of the highlights. That would be a great way to make the most of your time there. I’d also recommend checking out the Historic Key West Seaport and picking up food from Blue Heaven or Cuban Coffee Queen. I hope this helps!

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The 7 Most Beautiful Places You Need to Watch the Sunset in Key West

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Learn how to easily plan your dream trip to Florida!

3 Days in Key West: An Epic Weekend In Key West Itinerary

February 24, 2022 //  by  Florida Trippers

Are you looking for the perfect weekend in Key West? If so we have put together a three-day itinerary for your weekend in Key West! We have put together the best things to do in Key West . Your weekend in the Keys will be spent enjoying history, restaurants, state and National parks, beaches, nightlife, and more. We have crafted a plethora of tours to enjoy on your weekend trip to Key West!

Planning your trip to Key West last minute?

Make sure to book ahead! Hotels and tours often sell out the closer you get to your trip. Here are our top picks for Key West!

Top Experiences And Tours In Key West:

• Dolphin Watching And Snorkeling Eco Tour (Top pick!)
• Schooner Sunset Sail (2 hours)
• Reef Snorkel From Key West (Includes breakfast and mimosas)
• Hop-On Hop-Off Trolley Tour (Great way to see the city)

Top Places To Stay In Key West:

• Margaritaville Beach House Key West (Modern mid-range)
• Blue Marlin Motel (Affordable in downtown)
• Hampton Inn Key West (Waterfront with pool)
• Wicker Guesthouse (Great location!)

The first day of your Key West Itinerary will be spent exploring all the historical sites in Key West, the second day will take you to Dry Tortugas National park or Bahia Honda State Park and Day three will be spent exploring a corral, a food tour and shopping.

Before you plan your trip, make sure to check out The Best Times To Visit The Keys where we break down each month and talk all things weather!

Getting To Key West

Getting to a Key West weekend getaway is very easy! You can arrive by car, plane or boat.

If arriving by plane, the closest large international airport is Miami (MIA). Located just about a 3 hour drive north. If you do not want to rent a car, there is a shuttle bus from both FLL and MIA airport to Key West. However, you can also fly into Key West airport!

If driving you have the opportunity to stop along your drive through the Florida Keys. Located about 160 miles south of Miami, why not explore the upper and middle keys on your way to your weekend getaway in Key West.

For those coming from Fort Myers or Marco Beach areas, you can take the Key West Express ferry. The journey is 3.5 hours.

Getting Around During Your Key West Weekend Trip

We HIGHLY recommend renting electric bikes to explore during your weekend trip to Key West. It is such a fun way to explore with the fresh ocean breeze on your Key West weekend getaway. Another fun way to see the city is on a bike tour complete with a slice of Key Lime pie after biking all day!

You can use your own car if driving or rent a car at the airport. This is a great option if you want to explore the upper and middle Keys on a long weekend in key west.

Uber is easy to find here, and the hotels have shuttles. Key West is also a very walkable city, and you explore the downtown area on foot. Or try the hop on the hop-off trolley that operates through the city. You can book a tour here !

Are you a history buff? On the first day of your Key West weekend itinerary, we suggest exploring the historic sites across downtown Key West. Explore the home of a great American author or the winter getaways of former U.S. Presidents!

After a full day exploring and learning the history, it will be time to let loose on your weekend in Key West! Head on one of the amazing sunset cruises around the harbor or stay on land and enjoy a pub crawl across Duval street!

Stop 1 : Breakfast in Mallory Square

Located on the water in the Old Town, Mallory Square is the center of Key West. The Square has shops and restaurants that the whole family can enjoy! Why not start your day with breakfast here! We suggest breakfast at Cuban Coffee Queen.

Choose a hearty Key West-style breakfast or a Cuban breakfast to start fueling your body before spending the day exploring Key West!

After breakfast explore Mallory Square where street vendors and performers are often present.

Stop 2 : Harry S. Truman’s Little White House

Built in the 1890s, Harry Truman’s Little White House is Florida’s only presidential museum and is one of the best places to learn about American history.

Named after Harry Truman as he used this home as a winter getaway from DC. He use the house from 1946 through 1952. Presidents Taft, Eisenhower, Kennedy, Carter, and Clinton have all visited as well.

The entrance is $20 per adult or $10 per child. Included is a tour of the home and grounds where visitors can see how presidents lived while on their weekend in Key West!

Stop 3: Ernest Hemingway House

The next stop on your Key West itinerary is the Ernest Hemingway House . Located just a block from Duval street, the Hemingway House is a Spanish Colonial-style mansion. It is full of the famous writer’s personal items, historic furnishings, photographs, paintings, and more.

This is a must-see Key West destination for anyone who loves history, architecture, or literature! Worth noting the grounds are filled with the famous six-toe cats that are descendants of cats that roamed the grounds while Hemingway himself lived in the house!

Stop 4 – Sunset Cruise

Whether you are in town for a Key West couples getaway , a Key West girlfriend getaway, or a Key West bachelorette party we have the perfect way to end your first day! Why not end your first day with a Sunset Cruise with Buffet Dinner and Open Bar! There is truly nothing like being out on the calm and peaceful ocean while watching a gorgeous sunset.

On this two-hour cruise around the harbor, you will be fed a delicious dinner with favorites including pulled pork in mojo sauce, black beans, and rice, fish, mixed vegetables, pasta with mini shrimp, and more. You can dance on the upper deck, or sip a cocktail and watch the sunset!

For those looking for something a little more relaxing why not hop aboard the 2-Hour Sunset Sail on Schooner America 2.0 tour with two viewing decks and the calmness of open water.

Optional: Stop 5 -Pub Crawl

If you would rather stay on land, to end your first night on your weekend trip to the Florida Keys try a Duval Street Pub Crawl! Key West is known for its nightlife on Duval street, so why not let a tour guide you into the hottest spots in town with your admission and a cocktail at each stop included!

For those looking for a fun night out why not book this Drag Queen Guided tour that takes you to the most happening nighttime destinations in Key West! Featuring drinks, karaoke sing-alongs, dancing, and all the drama that comes along with being in the presence of a world-famous drag performer!

Make sure to check out the best bars and nightlife in Key West!

On Day 2 of your weekend in key west, we suggest heading on a day trip to Dry Tortugas! You can either do a half-day seaplane tour or a full-day boat tour! Check out our guide to avoid the big mistakes plus tips when visiting Dry Tortugas National Park !

After your trip to one of the best and hardest to reach National Parks, why not relax downtown and grab dinner and drinks on the water! You can pack and lunch even an alcoholic beverage to enjoy while on the island!

If getting to the Dry Tortugas is not an option on your trip, why take a day trip to Bahia Honda State Park!

Stop 1 : Dry Tortugas Day Trip

Dry Tortugas is a 100-square mile park made up of seven small islands and is located just about 80 miles from Key West. This tropical paradise is also home to the well-known and magnificent Fort Jefferson. A visit here mixes nature, history, and transports visitors to a remote place!

The only way to visit here is by private or chartered boat tour , chartered seaplane tour, or the Yankee Freedom Ferry . Reservations for the ferry fill up very quickly, so you’ll need to plan several months in advance. It is worth noting that the visit to Dry Tortugas can cost several hundred dollars and needs to be booked in advance. But it is 100% worth it!

For those who are adventurous enough, why not spend the night for some primitive camping in Florida !

Stop 2 : Visit Fort Jefferson

Most of the iconic photos you see from the Dry Tortugas is the red brick, Fort Jefferson. Take a tour of Fort Jefferson to learn about the island chain’s historical past as a prison. It once housed nearly 2000 inmates. You can also take a self-guided tour as well with numerous plaques spread across the fort. Make sure to put this on your list when doing a Florida Keys Road Trip!

Stop 3: Snorkling

No weekend in Key West is complete without a trip to Dry Tortugas. It is a great spot for snorkeling and scuba diving around the National Park. Less than 1% of the National Park is on dry ground, making the Dry Tortugas an underwater paradise!

With crystal clear water, gorgeous coral some rising 50ft high, it is truly spectacular! There are fish species here that don’t exist anywhere else in the world. Keep an eye out for  sea turtles as the island is named after the Spanish word for turtles!

The popular spots to go, scuba dive, include the Maze, the Bat Caves, Dante’s Inferno, Texas Rock, and the Windjammer Wreck one of the most beautiful shipwrecks in the world.

Optional: Bahia Honda State Park

For those who don’t have the time or budget for Dry Tortugas, head to Bahia Honda State Park . We have an entire guide on what to explore here!

Known for its iconic Florida Key scenery, sandy beaches, clear waters Bahia Honda State Park is the best place to visit on a weekend in Key West. Just under 40 miles from Key West, it only costs $8 per vehicle to visit!

You will want to arrive early on weekends or holidays as once capacity is hit, the park will close!

Make sure to check out some of our other favorite things to do in the Lower Keys in addition to Bahia Honda or check out our list of the Best Florida Keys Beaches for some more ideas of places to visit!

Stop 4: Dinner at Blue Heaven

You are sure to have worked up an appetite after exploring Dry Tortugas! We suggest heading to one of the best restaurants in Key West for dinner.

Head to the historic Bahama Village where you can enjoy the island flavors. From the fresh snapper in the yellow submarine sandwich to popular Caribbean “BBQ” shrimp or a vegan and vegetarian option, there are plenty of options!

Stop 5: Ghost Tour

After you return from your half-day trip to Dry Tortugas or Bahia Honda, why not spend your evening on a ghost tour of Key West! The best part is you will be transported by trolly along with the spooky and haunted sites across the island.

On day 3 of your weekend in Key West itinerary, you will be taking it easy after a jam-packed first two days and nights! You will start with an amazing boozy brunch spot, followed by either snorkeling the reef, taking food out, or purchasing handmade leather sandals!

Stop 1: Brunch at Bagatella

Bagatelle serves a breakfast hangover happy hour from 9 to 11:30 a.m. every morning. If you had a late night during your Key West bachelorette party head here, where you can enjoy fun alcoholic beverages with scrumptious brunch plates. Dive into a crab cake benedict, crispy fried French toast, or braised pork sandwich with pineapple slaw.

Stop 2 : Snorkeling and Breakfast

On stop 2 of your Key West getaway itinerary why not take a Key West: Reef Snorkel Morning Tour with Breakfast & Mimosas! This tour is 3 hours where you will visit the third longest reef in the world, snorkel, and enjoy a delicious breakfast accompanied by mimosas on your trip back to port!

Stop 3: Optional : Key West Food Tour

Next up, for those who want to stay on land is a Southernmost Food and Cultural Wal k ing Tour ! On this 5 stop tour, you will get to taste some of the most famous foods of Key West. Think conch fritters, fresh fish tacos, and the amazing key lime pie! Head to hole-in-the-wall places you would never find on your own!

Stop 4: Smather’s Beach

On your 3 days in Key West, you must visit one of the beaches. With half a mile of soft sand, Smathers Beach is the one to go to if you like lively, fun-filled beaches.

Smathers is a great beach with something for everyone like swimming, snorkeling, kayaking, parasailing, sunbathing, and beach volleyball. Plus there are food vendors and beautiful palm trees shoreline perfect for picnicking under!

Stop 5: Kino Sandal Factory

Since 1966, the Kino Factory has been a staple of any Key West weekend trip! Stop in the purchase handmade leather sandals that are hand-cut and produced on-site in this traditional sandal factory! Choose from over 17 styles with various color combinations for men, women, and children. 

Where To Stay In Key West

There are plenty of options if looking for places to stay in Key West ! From hotels, home rentals , camping , and more!

Make sure to check out our list of the Best Resorts In The Florida Keys ! There are some really epic resorts featured for couples, families, and more.

The Saint Hotel Key West, Autograph Collection

If you are looking to be in the heart of the action, The Saint is located just 4 minutes from Duval Street. This upscale hotel is also close to Ernest Hemingway and Smathers Beach. While the rooms are small, they are well-appointed and bright and airy, or splurge for a much larger suite!

Amenities include a restaurant and bar on-site as well as a chic outdoor pool with a waterfall and Dj on the weekends.

Check Rates: Booking.com

Key West Marriott Beachside

On our most recent trip to Key West, we stayed at the Key West Marriott Beachside. Located on 7 prime acres with oceanfront access with the pool as the centerpiece of the resort. This is truly one of the Best Places To Stay in The Florida Keys!

From the hotel’s marina, you can rent jet skis, kayaks, and paddleboards. There is a complimentary hotel shuttle downtown multiple times daily. Many of the balconies are oceanfront allowing you to relax and enjoy a sunset or ocean breeze from your town room!

If you have a car parking is $25 a night!

Dog-Friendly Home With Private Pool

Are you planning an extended weekend in Key West and want to bring your pups with you? This  Dog-Friendly Home With Private Pool  is the place to stay!

Located in Central Key West, you are in a prime location for exploring shops, restaurants, beaches, historic landmarks, and dog parks! The home is ready to accommodate up to 3 guests with 2 bedrooms, 2 beds, and 1 bath.

>>>Check Rates:  VRBO.com

Waterfront Oasis 

This 2 bedroom 2 bath home has amazing views of the ocean. This property  can sleep 6 people in 4 beds. This is truly one of the Best Places To Stay In Key West!

The property features plenty of outdoor seating, a grill, and a pool table. The home comes with life jackets and kayaks so that you can explore the channel that the house sits on.

Where to Eat During Your 3 days in Key West

Latitudes is one of the classiest restaurants in Key West. To reach it you’ll have to hop on a free ferry because Latitudes is on an island of its own!

With waterfront seating, delicious food, and excellent service, it’s open for breakfast, lunch, and dinner. For breakfast, savor the lobster benedict. For lunch, try the surf & turf burger. And for dinner, twirl up the Key West pink shrimp carbonara or cut into the lemon glazed yellowtail snapper.

Banana Café

This French-inspired restaurant serves up some of the best crepes in town. Enjoy them for breakfast, lunch, or dinner.

Try everything from the breakfast-themed la super crepe to the seafood-filled la Mahi piccata crepe to the popular homemade key lime pie crepe. At lunch, be a little adventurous and try the baked escargot. Or for dinner enjoy the half roasted duck, seafood risotto, and French country chicken. There are also a good number of vegetarian options available at Banana Café.

Hogfish Bar & Grill

Situated on Stock Island just 15 minutes from Key West, is Hogfish Bar and Grill. Known for its fresh seafood and oceanfront location, it is frequented by Florida Keys locals.

The hogfish tacos and hogfish sandwich – named after both the fish and the restaurant – are two of the most popular items on the menu. There is live music on the weekends.

Those looking for vegan and vegetarian options will want to head to The Cafe. Breakfast is served every Monday through Friday until noon. If a dish on the menu doesn’t fit your dietary habits, then simply ask your server for the vegetarian or vegan version.

On Saturday and Sunday, mornings switch to brunch service! We love the Polenta Cake Benedict with lemon-caper hollandaise. You can’t go wrong with the Caprese Egg Sandwich with house basil pesto, garlic spinach, grilled tomatoes, and fresh mozzarella.

Is Key West Worth Visiting? 15 Pros and Cons

Planning your next tropical holiday in Florida and wondering if Key West is worth visiting? Worry not. I’m here to help you decide.

Key West is one of the most popular destinations in the Florida Keys , and as a result, has made it very expensive to visit. But is it worth the hype?

After visiting myself, I realized that the answer might not be so simple. That’s why I’ve written this article on the pros and cons of visiting Key West and help you decide whether it is worth visiting or not.

Is Key West Worth Visiting?

Generally speaking, Key West is worth visiting. This island paradise is one of the most popular vacation destinations in the U.S. for a reason.

It’s home to one of the best beaches in the country such as the white sand Fort Zachary Taylor Beach, as well as some of the most fascinating historic sites in North America , such as the Ernest Hemingway House and The Truman Little White House !

Not forgetting that the foodie scene in the birthplace of Key Lime Pie is top-class; it rivals Miami, in our opinion! Plus, it’s one of the sunniest places in America, with a whopping 260 days of sunshine annually – so it’s fair to say if you’re a sun-worshipper (like us), Key West is 100% worth visiting!

Pros Of Visiting Key West

1. amazing key lime pie.

Key West is well-known for many things, but it’s perhaps most famous for being the birthplace of Key Lime Pie. This refreshing and indulgent dessert is named after the Key limes that are grown here, and – they are unique because their juice is yellow, not green!

Key Lime Pie is made of key lime juice, sweetened condensed milk, and egg yolk and is typically topped with a meringue topping. 

The best spot in Key West to try this delicious sweet treat is at the aptly named Key Lime Pie Bakery , a short walk from Duval Street.

You’ll notice the green benches out front before you see the store, where inside, they serve up Key Lime Pie in various ways, from standard slices to slices dipped in chocolate. You can even try out a Key Lime Pie on a stick!

2. Incredible Weather Year-Round

Key West and great weather go hand-in-hand. This tropical paradise is, after all, the most southern city in the U.S. and is, in fact, geographically closer to Cuba than it is to the closest Walmart (which is in Florida City, by the way!)

So, as you can guess, Key West enjoys balmy weather for most of the year – to be precise, it enjoys a whopping 260 days of sunshine per year compared to the national average of 205! 

And if you’re planning to visit Key West in the winter, you’re in luck as the Key West area enjoys some of the hottest temperatures of anywhere in the United States in December , with an average of 80 Fahrenheit!

But, the most popular months to visit Key West, Florida, are March and April, when temperatures range from 82 – 85 Fahrenheit with very little rainfall. The hottest months in Key West are June, July, August, and September when daily highs regularly rise over 86 Fahrenheit.

3. Epic Sunsets

If you love sunsets, then Key West is most definitely worth visiting for you.

Known for some of its most epic sunsets, there are many different ways to enjoy it in Key West. Two of the most popular are to head to the aptly named Sunset Key or to Mallory Square to watch the daily sunset celebration and enjoy the free entertainment on offer.

Every night, magicians, comedians, jugglers, clowns, etc., put on a show before the real show (the sunset). The festivities typically start two hours before sunset! 

Another great sunset spot is Fort Zachary Taylor Beach, regularly touted as the best beach in Key West. Bring your own beach chairs or picnic blankets, pack some snacks and drinks, and watch the sun set into the Gulf of Mexico as boats pass by. 

4. The City is Very Walkable

Due to its compact size, Key West is very walkable. Most of the restaurants, stores, and cafes can be found along Duval Street and Whitehead Street, as well as in Mallory Square.

In fact, we’d go so far as to say that you can walk pretty much everywhere in Key West, but if you don’t feel like walking, you can use the Key West Trolley, a hop-on-hop-off-bus tour that stops at the top attractions in Key West, like the Hemingway House and the Harry S. Truman Little White House. 

5. Incredible Food, and Not Just Seafood

As we said earlier, Key West is very close to Cuba (there are just 96 miles between the two destinations), so as you can guess, Cuban and Caribbean cuisine is a big thing in this island city.

So, expect to see Cuban bread and lots of meat with jerk seasoning on menus here. Because it’s a coastal city, seafood is extremely popular in Key West.

Depending on the time of year, you may find mahi-mahi, grouper, snapper, lobster, or the very tasty Key West pink shrimp dominating the specialty menu.

Some of our favorite restaurants when we visited Key West included Blue Heaven , a romantic eatery focusing on Caribbean cuisine and seafood.

Cafe Marquesa is another top pick from our trip to Key West, and it boasts a luxurious and elegant atmosphere, just off Duval Street. Come try their scallops and foie gras in a tranquil garden setting! 

While, if you’re after something a little more low-key, you can’t go wrong with Cuban Coffee Queen , a casual cafe known for its excellent coffee and sandwiches.

6. Lively Atmosphere and Vibrant Nightlife

Key West is famous for its nightlife, especially the vibrant Duval Street, which is lined with lots of fun bars and nightclubs. In fact, the “Duval Crawl,” aka the Duval Street bar crawl, is a rite of passage for any party-loving visitor.  

We recommend starting your night in Upper Duval, which has a more sophisticated vibe with lots of romantic wine bars. Grand Vin Wine Bar is our top pick for Upper Duval.

Then, ease your way down to the more raucous Lower Duval, which houses many late-night bars and nightclubs. Here, we like Rick’s Bar , home to the largest dance floor in the Florida Keys.  

7. Beautiful Scenery

As soon as you step foot in Key West, you’ll be captivated by its natural beauty, from bougainvillea-lined streets to picture-perfect white sand beaches. Not forgetting, it’s home to the Key West Garden Club, a tropical oasis where you can find the Key West Butterfly Garden and Perfume Garden .

This paradise-like island city is also within close proximity of some of the most beautiful destinations in North America, like Dry Tortugas National Park and Fort Zachary Taylor Beach! 

📚 Read More: What Is Florida Known For?

8. Interesting Historical Sites

Key West’s history is littered with tales of pirates and smugglers, which lies in stark contrast to the luxurious Key West today!

The best places to learn about Key West’s fascinating history are at the city’s top sites like the Truman Little White House , the former residence of the U.S. Naval Commander, and the Hemingway House , where the famed writer lived during the 1930s. 

Opposite the Hemingway House, you’ll find the Key West Lighthouse, which dates back to 1848 and helped boats navigate the shallow waters here for over 100 years.

It was decommissioned in 1969, and today, it houses a museum where you can learn all about Key West’s maritime history and the lighthouse keepers who once called the lighthouse home! 

9. Access to Dry Tortugas National Park

The hard-to-reach but breathtakingly beautiful Dry Tortugas National Park is just 70 miles from Key West. This park is huge with 100 square miles of mostly open water and seven tiny islands. It is only accessible by seaplane or, more commonly, by boat!

Most famous for being the home of magnificent Fort Jefferson (used as a prison during the Civil War), the park also boasts bright blue waters, coral reefs, abundant marine life (especially sea turtles), and bird life!

It’s super-easy to reach this remote National Park from Key West. Just hop on the Dry Tortugas National Park ferry from 100 Grinnell Street. It’s about a 2-hour and 15-minute ferry ride.

10. The Most Southern Tip of Continental United States

Key West is the southernmost city of the continental United States. And for anyone that questions whether this is true or not, the city has planted the Southernmost Point Buoy at the corner of South Street and Whitehead Street.

Since then, this Buoy has become of of the biggest attractions in Key West. No itinerary is complete without getting an iconic photo at this location!

Cons Of Visiting Key West

Key West is quite an exclusive vacation destination thanks to its remote location (it’s a 3-4 hour drive from Miami), and it attracts a mostly upmarket crowd.

In fact, Key West has some of the most expensive hotel rooms in the country during peak season (from March to May!) And when you add into the mix the fact that Key West is known for its upscale restaurants, it can dissuade some tourists from visiting. 

It’s also quite expensive to fly into Key West International Airport , so many budget-savvy travelers instead opt to fly into Miami and travel the 3-4 hours to Key West. 

2. Too Crowded

Key West is far from being a quiet beach destination in Florida and many tourists will tell you it is too crowded to be enjoyable.

Because the island is so small, even a bit of tourism can make the island feel busier than usual. It’ll help if you travel outside of the peak season, which is from March to May.

Another point to note is Key West is a popular cruise ship destination, and December through April are the busiest months for cruise ships. So, during these months, Key West will be flooded with cruise ship passengers during the day, meaning restaurants and activities will sell out quickly.

3. Better Beaches Elsewhere

Although the beaches in Key West, like Smathers Beach and Higgs Beach, are pretty, we think more beautiful beaches can be found elsewhere in the state and the other Florida Keys.

For example, the Gulf Beaches such as Clearwater Beach and Siesta Beach are more sandy and generally feature more pristine water than the beaches in Key West.

4. The Weather Can Be Too Hot and Tropical

If you’re traveling here from colder destinations, you may find the Key West weather too hot! I mean, with average highs of 92 Fahrenheit (33 C) in the summer, it’s definitely not somewhere to visit if you’re not a fan of sunshine.

Plus, Key West offers 260 days of sunshine annually, so cloudy, rainy days are few and far between. It is no wonder that it is one of the sunniest and warmest places in Florida in the winter .

The rainy or hurricane season (May through October) experiences very high humidity levels, which can be uncomfortable for some even if the temperatures are slightly lower. It is one of the worst times to visit Florida in general!

5. Traffic Can Get Quite Bad

It is surprising to find that the traffic in Key West is horrific, especially given its small size. Heavy traffic on this small island, particularly on weekends and holidays, can bring things to a standstill, which can be frustrating if you’re trying to get somewhere in a hurry.

Most highways in and around Key West, such as the Overseas Highway , are just two lanes, and passing is only allowed in specific sections – so bad luck if you get stuck behind a slow driver here!

Things To Do In Key West 

1. duval street.

The beating heart of downtown Key West – Duval Street is easily the busiest street in the Florida Keys. It’s a little over a mile long and is lined with restaurants, stores, and, of course, bars and nightclubs.

In fact, it is most famous for being the home of the “Duval Crawl” – a bar crawl and a must-do for partiers! Start your evening in a wine bar in Upper Duval, then catch the sunset celebrations in Mallory Square and end your night in one of the cool nightclubs on Lower Duval!

2. Mallory Square

Another vibrant hub of activity in Key West is Mallory Square, which we mentioned earlier as “the place” to watch the sunset because street performers take to the square every night to put on a show about two hours before sunset!

It’s also home to the Shipwreck Museum, Key West Aquarium, and Shell Warehouse & Sponge Market . And if you love to shop ’til you drop, you’ll be in heaven at The Shops at Mallory Square, an air-conditioned building that sells everything you could imagine!

3. The Hemingway Home and Museum

No trip to Key West is complete without a visit to the Ernest Hemingway House. Located opposite the Key West Lighthouse, it was the home of well-known American writer Ernest Hemingway in the 1930s.

It’s a very photogenic building with a fabulous in-ground pool and a great place to learn more about the famed author. Yet, perhaps the most interesting thing about this attraction is the many cats that live on the grounds.

They are all believed to be descendants of Hemingway’s pet cat, Snow White, who famously had six toes!

4. Southernmost Point of the Continental U.S.A.

Easily the most Instagram-famous spot in the whole of the Florida Keys is the Southernmost Point Buoy, which highlights that Key West is the most southerly city in the U.S. and marks 90 miles to Cuba! Spend a few moments here snapping photos and testing your eyesight to see if you can see Cuba across the water!

5. Fort Zachary Taylor Historic State Park

Not only is the 54-acre Fort Zachary Taylor home to Key West’s best beach, but it’s also one of the best sunset-watching spots in the Sunshine State . As well as that the Fortress here is a National Historic Landmark that played a very important role in Florida’s history. Conveniently, it’s just a 10-minute drive from downtown Key West.

Visiting Key West FAQs

Is it safe to visit key west, how to visit key west from miami, when is the best time to visit key west, so, is key west worth visiting.

If you have gotten to the end of the article, then you can see that there are definitely pros and cons of visiting Key West. Its unique location on the southern tip of the continental US gives travelers a unique experience, along with a lively atmosphere and nightlife that are quite enjoyable.

But there are cons to visiting Key West, such as the high prices and sub-optimal beaches. If you are looking for those things, perhaps check out some of the Gulf Beaches in Florida instead.

Disclaimer: Some of the links above are affiliate links. That means if you book or make a purchase through the links, we will earn a small commission at  no extra cost to you ! The money will help run this site! Thank you !

World Traveler, Travel Blogger, Photographer

LivingOutLau

Sean is the founder of the travel blog, LivingOutLau. He has been to over 30 countries in over 5 years of travel. Every day, he is traveling and sharing his discoveries of the world through exceptional travel guides on his blog!

Best Time to Visit Key West: A Month-By-Month Guide (2023)

December 17, 2022.

Table of Contents

Key West, Florida brings a slice of Caribbean vibes into Florida’s borders and offers a ton of fun the whole family can enjoy. But if you have your eye on the “Conch Republic” for your next family vacation, figuring out the best time to visit Key West  can be a little tricky.

Key West—the final island in Florida Keys—lies off the tip of Florida and is the southernmost point of the continental United States. It is connected to the mainland via the Overseas Highway, a series of stunning causeways that carry U.S. Route 1 over electric blue water and into the islands.

Key West is only 90 miles from Cuba – but even that 90 miles gives Key West more seasonal variation than the average Caribbean island. You’ll have to pay close attention to Key West weather when booking plane tickets.  

Also, because Key West primarily attracts American tourists, prices rise and fall dramatically based on peak travel seasons. 

All of this means you’ll want to time your trip carefully.

Fortunately, we’ve done the legwork and taken these factors into account in evaluating the best time to go to Key West and the other Florida Keys.

Keep reading for the details, and to learn what to expect month-by-month when visiting the Florida Keys with your kids – and why we think it’s a great option for a family trip.

Mango Tree Bottom Line 

The best time to visit Key West, Florida is from March to May, during the springtime shoulder season. Great weather, slightly more reasonable prices than winter months, and fewer crowds—but no hurricanes—all align to set the stage for a delightful family vacation.

Mango Tree Recommends 

Stay here… 

Santa Maria Suites for muliple bedrooms in the heart of Key West.

Sunset Key Cottages for luxury family cottages and a proper beach.

Don’t miss…   

This Half-Day Snorkel and Kayak Cruise ( 1000+ rave reviews !) 

This  Sunset Catamaran Cruise  (with live music) 

A  Hop-On Hop-Off Trolley Tour  with kids  

A unique  glass bottom boat tour  with the whole family

Pancakes at  Blue Heaven

And don’t forget… 

Book your  Key West rental car  early – and go for the convertible, you won’t regret it. 

Caribbean Family Travel Resources

Before we dive in, let’s be sure you have our best travel resources at your fingertips.   

Did you know we have a whole collection of recommended family hotels in the Caribbean? I’ll let you in on a secret, it’s sort of our pride and joy. 

Wishing someone else would just handle the logistics for a change? We also offer bespoke Caribbean family t ravel planning services. 

Our specialty? Helping parents identify the best Caribbean island and hotel for a top-notch family trip. Let us take the legwork off your plate. 

Now, cut yourself a slice of Key Lime pie and start planning your drive down the Florida Keys…

This post contains affiliate links from our trusted partners

Overview: when is the best time to visit key west.

Key West is the most recognizable of the hundreds of islands in the Florida Keys .  It’s the end point for most road trips through the island chain, and a top family destination.  But when to do? In evaluating the best time to go to Key West, we considered:  

• Hotel availability and rental prices
• Key West weather, including hurricane season
• Seasonal events and festivals
• Potential crowds and
• Activities available for families

So how did we land on March to May as the best months to visit Key West? Here’s the calculus.

While you can certainly enjoy Key West year-round, the winter and summer seasons have some drawbacks.

Wintertime is peak season. From late December through February, accommodations are as costly as they get. Plus, the Keys can get quite cool in December and January, with temperatures dipping into the 60s.

The practical effect of the cool Key West weather? It may be too cold to really enjoy swimming in the ocean or unheated pools. 

On the flip side, there are plenty of festivals and events throughout the winter, all taking advantage of the crowds who have made their way south for warmer weather. See below for some examples.

The summer season offers the cheapest hotel prices.  But with kids out of school and headed to the beach, you may find crowds at family-friendly hotels.  Temperatures will be hot and muggy in July and August, with Florida’s rainy season in full swing.  

Hurricane season in the Caribbean—including Key West—runs from June to November.  While we’re fans of Caribbean off-season travel, even during fall months like October, you should expect plenty of afternoon showers this time of year.  You also face heightened risk of having your trip disrupted by a major storm.  

That leaves the sweet spot: March to May, the best time of year to visit Key West . 

In late March, you’ll get Key West at its best weather. Tourist season is still going strong, especially during spring break weeks, but hotel prices start to drop from the end of February into March.

And as you head into April and May, those prices decrease even further — while the weather keeps getting warmer and better!  That’s the best time to grab a car at the Miami airport, and head south through the Florida Keys. 

Check Rental car rates in miami for april and may now!

Where To Stay In Key West With Kids

Key West may not scream “kid-friendly destination” on first glance, but a drive through the Keys, culminating with a few days in Key West, is a road trip every family should take. 

Once you arrive at the end of the United States, there are lots of family-friendly hotels to choos from! 

Our full hotel profiles are coming soon, but we’ve got an eye on these kid-friendly properties:

For a private island choice, book luxury stay at  Sunset Key Cottages , or a spacious unit at  Parrot Key Hotel & Villas . Both properties sit on private keys just a short boat ride from Key West. You’ll have easy access to the energy of Duval Street but a quiet place to retreat with the kids.

To stay right downtown, walking distance from art galleries, restaurants, live music, and more, the  Santa Maria Suites  offer families condo-style units with multiple bedrooms and a cozy courtyard pool for unwinding at the end of the day.   Havana Cubana  also has a great pool.

If you’re driving south, and love a marina view, the 100-room  Perry Hotel and Marina  just outside Key West on Stock Island is another great choice. With three restaurants, live music nightly, two waterfront pools,and  firepits, it’s a destination in its own right, but offers easy access to Key West, with just a 15-20 minute drive into town. 

Key West By Month

We’ve given you our logic for the ideal time to visit the Florida Keys. But maybe you want to head there a different time of year, or perhaps have limited flexibility. 

Let’s walk through a month-by-month breakdown of weather, prices, crowds, and events in Key West so you’ll know exactly what to expect whenever you decide to go!

Key West in January

January closes out the winter season in Key West. This is the coldest month on the island – the average temps range from a high of 74 degrees to a low of 64 degrees.

If you are traveling to the Florida Keys in January with kids, know that it may be too cold to enjoy the ocean or unheated pools during the winter months. If you and your kids want to enjoy swimming, look for a heated pool when visiting Key West in January.  

Despite the cool weather, January is still the height of peak season for Keys tourists, as the rest of the continental US is far colder. This means accommodation prices are about the highest they get.

But on the bright side, the island is buzzing with holiday fun and annual festivals in January, including: 

• The Southernmost Regatta
• Key West Literary Seminar
• Key West Food & Wine Festival
• The Florida Keys Seafood Festival

Key West in February

Peak tourist season remains in full swing in February, with hotel rates peaking to match. For prices, this may be the worst time to visit Key West.

That said, Key West weather in February is pleasant, with mild temperatures averaging from a high of 76 degrees to a low of 66 degrees. This is also the island’s driest month of the year, with plenty of sunshine and very little rain.

Just like in January, if swimming is at the top of your family itinerary, consider finding accommodations with a heated pool. At 72 degrees, the ocean will be too chilly for anyone not looking for a heart-stopping cold plunge—but there’s so much to see in the Keys beyond the ocean that you can still have a great time.

Key West in March

And now we’re getting into the best time to visit Key West, especially later in March. Average temperatures float around a high of 78 degrees and a low of 68, with low humidity and sunny days. 

In Key West in March, you can break out your favorite swimsuit , load your best beach bag with cold drinks, and settle into a proper beach vacation.

There are also minimal threats of hurricanes or other harsh tropical storms in spring.

March is right on the edge of peak tourist season in Key West, marking the start of the spring shoulder season. Prices start to come down as the snowbird crowds slowly disperse. That said, you won’t get rock bottom prices this month: Between school spring breaks and clear blue skies, you’ll still pay a premium for Key West’s best weather.

Key West in April

  Key West is beautiful in April, with warm weather that’s ideal for beach lounging and swimming. Temperatures range from a high of 81 degrees to a low of 72, and humidity is as low as it gets. The crowds continue to get lighter, while prices continue to creep down.  This might be the perfect time to visit the Florida Keys.

April is also one of the best times to visit the Florida Keys for fun annual events and festivals. Join in the yearly Key West independence festivities at the Conch Republic Independence Celebration , or dance and experience Afro-Caribbean culture at the Afro Roots World Festival .

Key West in May

May is also a great shoulder month in Key West. Temperatures hit their tropical stride, with an average high of 85 degrees and a low of 76 degrees. The warmth, sun, and clear skies are ideal for those who like watersports and beach fun, and some would say May is the best time to travel to Key West.  If you head to Key West in May, you’ll sneak in right before hurricane season and Florida’s rainy season.

May is perhaps the best time to visit the Florida Keys if you want to go  snorkeling with kids , as the ocean feels warm, yet still refreshing. Fans of music will also enjoy the week-long Key West Songwriters Festival , the largest of its kind in the world.

Key West in June

June is the start of low season in Key West, which means hotel and resort prices will see a big drop. It’s one of the most affordable months to visit Key West – making it one of the best times to visit the keys for budget-minded families.

By June, summer has arrived and Key West’s weather is no longer ideal, with temperatures creeping up to an average high of 88 degrees and a low of 79. Humidity is quite high, and the island’s rainy season is well underway.

There will still be plenty of sunny days, however, and Key West Pride is an exciting festival taking place this month. June also is arguably the best month to visit  Dry Tortugas National Park , just off the cost of Key West.

If you don’t mind humidity and afternoon showers, consider a trip to Key West with your kids at the beginning of their school break.

Key West in July

Temperatures continue to climb in July, with an average high of 90 degrees and a low of 81. July is one of the hottest, rainiest, and muggiest months in Florida, and the Florida keys are no exception.

While the weather may not be as enjoyable, July is perhaps the cheapest time to go to Key West. Whatever family beach resort  you’ve had your eye on, it is a great chance to snag a room without the usual sticker shock. It will also be quite easy to book popular tours for your family.  

Ernest Hemingway is among the most notable of Key West’s famous former residents. If your high schoolers are enjoying (or suffering through…) The Old Man and The Sea, then the Hemingway Days  Festival  may help bring the novels to life.  

We spent July 4th in Key West a few years back, and while we remember the energy of Duval Street, we don’t remember rain interfering. So don’t write off the option of a July trip to the Keys. 

What better way to kick-off summer than with the 4th of July Weekend Key Lime Festival ? If you’re super into Key Lime pie, this festival alone might make July your  best time to visit the Florida Keys. 

Key West in August

August is the hottest month in Key West, with average temperatures ranging from an average high of 91 to a low of 81 degrees. The humidity is also quite high, with plenty of rainfall.  For those sensitivy to humidity and weary of rain, August is probably the worst time to visit Key West. 

That said, as a general rule, we don’t shy away from off-season Caribbean travel here at Mango Travel. Despite the risk of rain and the high humidity, we love exploring our favorite destinations in the quieter summer months.

If you’re traveling on a budget and want to avoid droves of crowds, long lines, and restaurant waits, August is your best bet. Enjoy spacious, care-free beach days with your toddlers , cheap accommodations, and easy access to Duval Street nightlife.  No reason to let afternoon showers scare you away.

One exception to these low-key August weeks may be Key West Lobsterfest , where the island kicks off lobster season with a massive party, which draws more crowds.

Protect Your Trip To Key West!

Do not let the rainy season scare you away from Caribbean travel! There’s no reason to shy away from Caribbean travel during the rainy season (July to November). Even if you see storms in the forecast, we’re typically just talking about afternoon rain showers—-a great time for a nap.  

That said, approach your trip with eyes wide open — and with a safety net. Caribbean travel during hurricane season (July to November) always comes with the risk of tropical storms. 

This is the most important time of the year to buy travel insurance, in case your trip gets impacted by a storm and you need to pivot and change destinations or dates.

We recommend that you get a travel insurance quote from  IMG global . On top of having comprehensive medical, cancellation, and luggage protection, the hurricane protection that comes with the Travel SE plan is better than most. If NOAA issues a hurricane warning or watch for your destination 24-72 hours before departure, trip cancellation benefits kick-in (read the fine print for all plan details, of course).  

Key West in September

Key West weather in September is still quite rainy and humid. Temperatures begin to fall, but not by much, with an average high of 89 degrees and a low of 79. The island is still relatively crowd-free – the kids are back in school, after all — and hotel prices are reasonable. While Key West in September is quieter than peak months, it still marks the annual  Key West Brewfest .

Key West in October

October is the start of the fall shoulder season in Key West. Storms abate and rain is less frequent, while temperatures begin to offer a little relief from the summer heat, averaging from a high of 85 degrees to a low of 76.

More visitors are returning to the island now that hurricane season is on the way out. If your kids have a school fall break, Key West may make a great destination for a quick October getaway.

That said, the island’s adult energy starts to come alive in October, as electric events like Fantasy Fest  kick off. This racy festival is probably too much for young kids, so don’t let it surprise you!

Key West in November

November is another good month to take advantage of shoulder season. As for Florida Keys weather in November, average temperatures float somewhere between a near-perfect 79 and 72 degrees.

Hurricane season isn’t technically over, though. That’s why November falls just short of being one of the top months for a visit to the Florida Keys. You may still get some storms, and a late-season hurricane could blow through.

The tradeoff is getting to avoid the large December and January crowds.  And prices are still reasonable before peak season hits. Get a babysitter and take in a show at the Key West Film Festival .

Key West in December

The weather in Key West is quite idyllic in December, with temps ranging from 77 to 70 degrees, and clear, sunny skies. Because December is the start of peak season, there are plenty of local events to enjoy.  

By the end of December, though, temperatures start to drop, so we’ll repeat our reminder here to prioritize heated pools if you’re headed to Key West over the holidays. Don’t be surprised by the Florida Keys weather in December.  If you’re heading to the Keys expecting it to be hot every day, this would be one of your worst times to visit the Key West. 

With endless activities (including family-friendly favorites like the Lighted Boat Parade ) and perfect lounging weather (if not swimming), it’s no surprise that many others have caught on too. 

Hotel prices reflect that December is a busy, popular month—especially during the week between Christmas and New Year’s Eve.

Ready to Book Your Caribbean Family Getaway?

There you have it! Our month-by-month guide to the weather, tourist trends, and hotel prices in Key West.

Want some help planning your tropical family getaway? That’s why we are here. Schedule a call to chat about our favorite Key West hotels for your next tropical getaway!

Get Caribbean Family Travel Tips Right Into Your Inbox 

If you found this post helpful, don’t miss our other  Caribbean destination guides for families . 

And for even more Caribbean and family travel inspiration, sign up for our biweekly newsletter! We feature a new destination each month, highlighting our favorite hotels and family travel tips. Keep the travel dreaming coming all year long. 

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Key West Express Ferry to Paradise

Chill out - relax - enjoy - explore.

Experience the ultimate getaway as our jet powered catamarans whisk you away to Key West ~ the Vacation Spot of Pirates, Poets, Presidents & Partygoers!   Famous for artists, explorers, musicians, fun filled events and the best in recreational water activities.

Indulge in a refreshing tropical beverage from our bar or savor a delicious snack from the galley as you set sail from Fort Myers Beach or Marco Island, gliding over the pristine turquoise waters of the Gulf of Mexico to the Southernmost Point of the United States.

WE LOOK FORWARD TO WELCOMING YOU ABOARD!

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INDIVIDUALS

15 or More Passengers

We offer departures from two convenient Southwest Florida locations; Fort Myers Beach (year round) and Marco Island (seasonally) to Key West, Southernmost Point of the United States.

Boarding & Departure Times

• Ft. Myers Beach to Key West :    Boarding begins at 7:00AM. Boarding required no later than 7:30AM. (8:00AM departure)
• Marco Island to Key West :           Boarding begins at 7:00AM. Boarding required no later than 7:30AM. (8:00AM departure)
• Key West to Ft. Myers Beach :    Boarding begins at 5:00PM. Boarding required no later than 5:30PM. (6:00PM departure)
• Key West to Marco Island :           Boarding begins at 4:00PM. Boarding required no later than 4:30PM. (5:00PM departure)

Schedules and times are subject to change. Travel time and actual time on Island varies depending on weather & sea conditions

however, plan on approximately 3.5 hours between ports.  

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Places To Go

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 100 Grinnell Street  Key West, FL 33040

  239-463-5733

Fort Myers Beach

 1200 Main Street  Ft. Myers Beach, Florida 33931

Marco Island

 951 Bald Eagle Drive  Marco Island, FL 34145