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Schooner Sailing Schedule

2024 j. & e. riggin sailing dates.

PLEASE NOTE: Links to trip particulars will show information that reflect the  current sailing season . Once the current season ends, the next year’s schedule will be updated with proper dates, instructors, and details.

Available Promotion(s):  Book your 2024 trip before February 1, 2024 for a 5% early booking discount (10% for repeat passengers). 

*Schooner discounts do not apply to the 207 Creatives Rug Hooking Getaway. Please go to  www.Facebook.com/207Creatives  for details, pricing, incentives, and discounts.

*  Discounts and promotions are available for  new  reservations only.   Only one offer can be applied to your reservation. Promotions may not be combined with any other offer, discount, or charter rate. Cancellation of trip and re-booking with a new discount or promotion is prohibited.

Sailing Charters?  If you are interested in scheduling a  sailing charter  please call or  email .  If you don’t see a date on the schedule that is just perfect for you, we are happy to work with you to make it happen.

Please keep in mind that dates and prices are subject to change any time before December 1st of the previous sailing year. 

Rewards & Savings for Our Loyal Passengers

You have choices when it comes to how you will spend your vacation time. We know it and appreciate that our customers choose us again… and again.

Over the years, we have steadily increased the rate of our repeat business. This says—and means—a lot. First, you must enjoy the time you spend with us. Second, you must see the value in the experience we offer. Third, you’re drawn to the excitement of sailing along the coast of Maine… on a historic schooner, to boot!

The way we see it, every windjammer cruise experience is an opportunity to deepen our customer relationships and build value through relevance and real advantages to choosing us. That said, we offer discounts to returning guests who book early for their favorite cruises. 

Click here to book your Maine sailing vacation .

Things to Note:

  • While we feel every sailing cruise is special, we do offer some windjammer trips with events or with a special focus. You can find descriptions under the “Schedule” menu.
  • We board every trip the evening of the first date listed between 5 p.m. and 6 p.m.
  • To check availability or reserve your cabin please email us or give us a call at 1-800-869-0604.
  • There is a 5% discount if reserved  BEFORE February 1st (of the current sailing season).
  • A deposit of $350 reserves a berth on any cruise, the balance is due 6 weeks before your sailing date.
  • Cancellation Policy: Due to our small size, cancellations or rescheduling of dates affect us significantly. We limit the number of guests to a maximum 24 passengers each trip to keep our guests’ experience personal and customized. As a small, family-owned and operated business, this means that every booking is important to ensure an exclusive, authentic experience, and excellent service. All cancellations made 8 weeks before your arrival are eligible for a refund less a $150 per person cancellation fee * . For cancellations made on or inside 8 weeks before your boarding date any and all payments are non-refundable unless we are able to rebook the entire space. If we are able to fill the entire space, any payments will be refunded less a $150 per person cancellation fee. If your space is not completely filled, any payments are forfeited. If you need to change your trip date and do so before your final payment is made 6 weeks before sailing, any payments made can be applied to a future visit. If the date change happens on or inside of 6 weeks there is a $150 per person change fee.  * In the case of natural disaster or pandemic, please understand that we are a micro-small business and we are unable to issue a refund.  ( updated 5/2020 )
  • Trip Cancellation Insurance Recommended:  Because the Schooner  J. & E. Riggin  serves a limited number of guests, we strongly suggest that you purchase trip cancellation insurance. If you choose not to purchase trip insurance and an unforeseen event keeps you from being able to travel to Schooner  J. & E. Riggin , we will be unable to refund your deposit and/or paid balance as set forth in our cancellation policy. We do not offer insurance directly but do recommend Allianz Travel Insurance. Their toll-free number is 1-866-884-3556  or visit AllianzTravelInsurance.com . Of course you may use any travel insurance company you prefer. 

We look forward to being a part of your Maine windjammer cruise.

Gift Cards!

Heard on the Docks…

“We want to thank you for all you did to make sailing on the J&E Riggin such a memorable experience. I had looked forward to it so much for so long that I was afraid that the actual experience could not live up to the anticipation. It did!”

~ Harry & Karel S., MO

“We had the time of our lives on the trip, and couldn’t imagine being with a better ship, crew, and shipmates. We enjoyed being entertained by your singing and your jokes in the evening, and just the whole relaxed pace of the week. We appreciated the great cooking and the all-around friendliness of all the crew, a direct reflection of the two of you.”

~ John & Doug P., UT

About the Riggin

Schooner J. & E. Riggin is a proud member of the Maine Windjammer Association

Copyright © 2018 - 2024 Schooner J. & E. Riggin. All rights reserved.

windjammer cruises 2024

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Each of Windstar Cruises yachts accommodates between 148 to 342 guests. This intimacy provides you with the luxuries of time, space, and freedom to immerse yourself in both the journey and the destination - in ways you may never have imagined possible.

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Caribbean 6 Night Sailings

windjammer cruises 2024

Homeport:  Rodney Bay, St. Lucia ST. LUCIA  -  Anse Chastanet   |   Pigeon Island MARTINIQUE  -  Grande Anse D’Arlets   |   Pt Anse D’Arlets   |   St Pierre

Wrap yourself in a lush blanket of green, as you trek through the rainforest to the sound of wild macaws and cascading waterfalls.

Take an afternoon swim in the shadow of the majestic Pitons. Try horseback riding or ziplining. You might happen upon an abandoned plantation, or a smoldering volcano that serves to remind you that the hearts of these islands beat to the rhythm of nature.

Savor Creole cuisine with the locals, in a picturesque fishing village where colorful gingerbread houses dot the seashore. Eclectic island boutiques and open-air markets feature Caribbean madras, one-of-a-kind jewelry, French perfumes and locally distilled rhum.

Sail around the bend to a secret oasis, and sip a “sundowner” as the day comes to an end, and the stars light up the sky to guide the way home. If you love nature, boutiques, and a touch of French culture, this is the adventure for you!

2024  June | July | August | November | December – VELA 2025  December – VELA

windjammer cruises 2024

Homeport:  Frigate Bay, St. Kitts St Kitts   |   Nevis   |   Antigua

The British loved their sea battles, and left plenty of evidence of that behind in this corner of the Caribbean. Explore sprawling hillside fortresses for magnificent views and plentiful photo-ops.

Enjoy high tea at a historic plantation, stroll the gardens, and delight in the beautiful foliage. Choose a handmade, island-inspired batik sarong to wear to the beach bonfire. Go bird-watching and monkey spotting.

Puffy clouds float like halos around mountain peaks, and remind us how close we are to heaven on earth. Have a decadent day sipping Killer Bees and sifting sand through your toes.

2024  April | May | June – VELA

windjammer cruises 2024

Homeport:  Philipsburg, St. Maarten St Maarten   |   St Barth's   |   Anguilla

Your adventure begins in Sint Maarten / St. Maarten: one island, two countries. The Dutch side offers a bustling downtown with casinos, chic boutiques, and the chance to sail America’s Cup! The French prefer their beaches “au naturel”, so leave your inhibitions at the invisible border.

Devour a juicy cheeseburger in paradise at Le Select, the inspiration for Jimmy Buffett’s song. Shopping is fabby at high-end boutiques (and semi-reasonable ones, too)! Get a swim in and sip a grapefruit margarita at a chichi beach club.

Today is another day in paradise! You get to paddleboard, snorkel, and hike trails that lead to majestic views. No shopping, no WIFI; just you getting to know the pristine nature preserve.

Tasty Guavaberry Coladas and other passion-inspiring frosty concoctions tempt your tastebuds. Beach bars are plentiful but don’t miss a day of basking in the sun on a postcard- perfect blinding white crescent beach.

2024  February | March | April – VELA 2025  January | February | March – VELA

windjammer cruises 2024

Homeport:  St. George’s Grenada Carriacou   |   Mayreau   |   Tobago Cays

If your perfect escape includes secluded isles ringed with white sand beaches and swaying palms, allow us to tempt you with a sail through the Windward Islands!

You’ll swim with sea turtles in the protected waters of marine preserves, and snorkel above colorful reefs that come alive with waving sea fans and electric blue damselfish.

Hike to spectacular vistas, and snap yourself next to cannons protecting the ruins of old forts. Purchase a unique piece of scrimshaw or a handcrafted model boat from a local artisan.

Experience the local nightlife with an intoxicating “cultural walk”. Lime with the locals and dance the night away on this progressive tour of island-style watering holes!

2024  October – VELA 2024  June | July | October | November | December – DIAMANT 2025  June | July | November | December – DIAMANT 2025  November – VELA

windjammer cruises 2024

Homeport:  Road Town, Tortola British Virgin Islands

Live the lyrics of your favorite trop rock song, while sipping high-octane rum at legendary beach bars.

Be the first to leave your footprints in a heavenly palm-fringed hideaway. Snorkel the kaleidoscopic offshore reefs. Let loose your inner pirate! Search for buried treasure in a swim-up cave, or in the crevice of a giant boulder.

Kayak under the stars, surf the north coast, and paddleboard in the calm waters of Sir Francis Drake’s Passage.

Once you’ve had your fill of life aquatic, explore the wilder. more rugged side of the British Virgins with a hike on a mountain trail and a peek into a bat cave. Yikes!

There’s no denying the British influence as you stroll the cobblestone streets and pop into art galleries, shops, and museums. Share a pint of grog with your shipmates at a raucous pub. Offer up a toast to sublime sailing, full moon parties, and living a pirate’s life!

2025  March | April | May – VELA

windjammer cruises 2024

Homeport:  Providenciales (Provo), Turks and Caicos Turks and Caicos

Take a few swift fin kicks from the brilliantly white sand beach, and you'll be waving hello to friendly moray eels, graceful manta rays, and energetic schools of tropical fish. The Turks and Caicos islands are home to one of the largest barrier reefs in the world! Flocks of pink flamingos stand watch from the shore, awaiting the annual winter migration of humpback whales. Savor a rummy-delicious Caribbean cake, and "wine" in time to the beat of Ripsaw music. Come for the charm, the luxe, and the sailing divine!

2024  February | March | April | May – DIAMANT 2025  February | March | April | May – DIAMANT

windjammer cruises 2024

Homeport:  Young Island, St. Vincent Bequia   |   Canouan   |   Mustique   |   Tobago Cays

If you listen closely, you'll hear a mermaid's laughter rising from the turquoise deep, while pods of migrating whales murmur and sing their approval. Monkeys chatter. Sparks light up the sky from volcanoes which color the beaches a dark charcoal, speckled with diamond dust.

The West Indies are wild, wonderful, and undiscovered. Immerse yourself in their beauty and hide in plain sight....Sail Vela to sun-dappled islands and find yourself!

2025  June – VELA

Greek Isles 10 Night Sailings

windjammer cruises 2024

Homeport:  Kos Town, Kos Island Kos   |   Panteli   |   Arki   |   Patmos   |   Loipsi   |   Kalymnos   |   Levitha   |   Kefalos   |   Tilos   |   Nisyros

Your adventure begins in Kos, an island paradise located in the southeastern Aegean Sea. From here, you will island-hop to ports of call rich in history and culture.

Hike to an abandoned church. Watch tiny model boats, built by a loving grandfather for his adoring grandchildren, bob in a cove. Wild goats tempt gravity on the rocky hillsides. Swim in the clear, indigo blue sea, and dry yourself under the warm rays of the Mediterranean sun.

Explore towns and villages. Shop at the local markets, and admire the strikingly white buildings, framed by incredibly blue, cloudless skies.

Slip away to a vine-covered taverna and partake in the endless pitchers of local wine sipped by visitors and festive locals. Dine on delicious octopus, and savor the ripe tomatoes in a chunky Greek salad. Indulge in a bowl of creamy homemade yogurt, drizzled in golden honey.

Overnight in a sheltered bay next to an ancient monastery. Breathe in the salt air and calmness of the night, as you gaze at the twinkling stars above. If you listen closely, you might hear soft music wafting through the galaxies from Lyra, the harp constellation.

2024 + 2025  April | May | June | July | August | September | October – LYRA

Caribbean 12 Night Sailings

Extended sailings are perfect for those who prefer a schedule ruled by the sun, moon and tides. The ports of call are not pre-planned. Each day will bring a new destination – a perfect little island present, wrapped in palm trees, white sands, and turquoise waters.

Save a lot on high season 12-night Explorer cruises, save even more on 12-night Captain’s Specials.

windjammer cruises 2024

DIAMANT May 26 - June 7, 2024 Leeward + French West Indies Home port: Rodney Bay, St. Lucia + Philipsburg, St. Maarten Visit a selection of: Anguilla   |   Antigua   |   Dominica   |   Guadeloupe   |   Iles des Saintes   |   Martinique   |   Montserrat   |   Nevis   |   St. Barths   |   St. Kitts St. Lucia   |   St. Maarten June 9 - 21, 2024 Windwards + French West Indies Home port: St. George’s, Grenada + Rodney Bay, St. Lucia Visit a selection of: Bequia   |   Canouan   |   Carriacou   |   Grenada   |   Mayreau   |   Petit St. Vincent   |   Sandy Island   |   St. Lucia   |   St. Vincent   |   Tobago Cays Union Island   |   Young Island

VELA April 14 - 26, 2024 French West Indies Home port: Philipsburg, St. Maarten + Frigate Bay, St. Kitts Visit a selection of: Anguilla   |   Antigua   |   Dominica   |   Montserrat   |   Nevis   |   Saba   |   St. Barths   |   St. Kitts   |   St. Maarten June 9 – 21, 2024 French West Indies Home port: Frigate Bay, St. Kitts + Rodney Bay, St. Lucia Visit a selection of: Anguilla   |   Dominica   |   Guadeloupe   |   Iles des Saintes   |   Martinique   |   Montserrat   |   Nevis   |   St. Barths   |   St. Kitts   |   St. Lucia December 8 – 20, 2024 French West Indies Home port: Rodney Bay, St. Lucia Visit a selection of: Dominica   |   Guadeloupe   |   Iles des Saintes   |   Martinique   |   Montserrat   |   Nevis   |   St. Kitts   |   St. Lucia

windjammer cruises 2024

DIAMANT December 22, 2024 to January 3, 2025 Windward Islands + French West Indies Home port: St. George’s, Grenada + Rodney Bay, St. Lucia Visit a selection of: Bequia   |   Canouan   |   Carriacou   |   Grenada   |   Mayreau   |   Petit St. Vincent   |   Sandy Island   |   St. Lucia   |   St. Vincent   |   Tobago Cays Union Island   |   Young Island January 5 - 17, 2025 French West Indies + Leeward Home port: Rodney Bay, St. Lucia + Philipsburg, St. Maarten Visit a selection of: Anguilla   |   Antigua   |   Dominica   |   Guadeloupe   |   Iles des Saintes   |   Martinique   |   Montserrat   |   Nevis   |   St. Barths   |   St. Kitts St. Lucia   |   St. Maarten

VELA Jan 5 - 17, 2025 French West Indies Home port: Rodney Bay, St. Lucia + Frigate Bay, St. Kitts Visit a selection of: Anguilla   |   Dominica   |   Guadeloupe   |   Iles des Saintes   |   Martinique   |   Montserrat   |   Nevis   |   St. Barths   |   St. Kitts   |   St. Lucia March 16 - 28, 2025 Leeward + British Virgin Islands Home port: Philipsburg, St. Maarten + Road Town, Tortola Visit a selection of: Anguilla   |   Cooper Island   |   Jost Van Dyke   |   Norman Island   |   St. Barths   |   Salt Island   |   Tortola   |   Tortola   |   Virgin Gorda

windjammer cruises 2024

DIAMANT May 25 - June 6, 2025 French West Indies + Leeward Home port: Philipsburg, St. Maarten + Rodney Bay, St. Lucia Visit a selection of: Anguilla   |   Antigua   |   Dominica   |   Guadeloupe   |   Iles des Saintes   |   Martinique   |   Montserrat   |   Nevis   |   St. Barths   |   St. Kitts St. Lucia   |   St. Maarten June 8 - June 20, 2025 French West Indies + Windward Islands Home port: Rodney Bay, St. Lucia + St. George’s, Grenada Visit a selection of: Bequia   |   Canouan   |   Carriacou   |   Grenada   |   Mayreau   |   Petit St. Vincent   |   Sandy Island   |   St. Lucia   |   St. Vincent   |   Tobago Cays Union Island   |   Young Island December 7 - 19, 2025 Windward Islands Home port: St. George’s, Grenada Visit a selection of: Bequia   |   Canouan   |   Carriacou   |   Grenada   |   Mayreau   |   Petit St. Vincent   |   Sandy Island   |   St. Vincent   |   Tobago Cays   |   Union Island   |   Young Island

VELA May 11 - 23, 2025 British Virgin Islands + Leeward Home port: Road Town, Tortola + Philipsburg, St.Maarten Visit a selection of: Anguilla   |   Cooper Island   |   Jost Van Dyke   |   Norman Island   |   St. Barths   |   Salt Island   |   Tortola   |   Virgin Gorda May 25 - June 6, 2025 French West Indies Home port: Frigate Bay, St. Kitts + Rodney Bay, St. Lucia Visit a selection of: Anguilla   |   Dominica   |   Guadeloupe   |   Iles des Saintes   |   Martinique   |   Montserrat   |   Nevis   |   St. Barths   |   St. Kitts   |   St. Lucia November 16 - 28, 2025 Windwards + French West Indies Home port: St. George’s, Grenada + Rodney Bay, St. Lucia Visit a selection of: Bequia   |   Canouan   |   Carriacou   |   Grenada   |   Mayreau   |   Petit St. Vincent   |   Sandy Island   |   St. Lucia   |   St. Vincent   |   Tobago Cays Union Island   |   Young Island November 30 - December 12, 2025 French West Indies Home port: Rodney Bay, St. Lucia Visit a selection of: Dominica   |   Guadeloupe   |   Iles des Saintes   |   Martinique   |   Montserrat   |   Nevis   |   St. Kitts   |   St. Lucia

Island Windjammers

ALWAYS ON ISLAND TIME

New England With Love

Sailing on a Maine Windjammer Cruise: Everything you Need to Know

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Considering sailing on a Maine windjammer cruise? There is absolutely no better way to experience the coast of Maine .

In this guide, we’re going to tell you all about what to expect on this fabulous Maine sailing trip.

The best Maine windjammer cruises involve sailing on a traditional schooner out of Rockland, Maine. My first trip was with a friend, Nicki. I had little idea what to expect; I only knew I was anxious to spend a few days “at sea” on a totally different kind of journey.

When Nicki offered to bring me with her on a “Lobsters and Lighthouses” cruise, I agreed immediately. Would I like to go sailing on an authentic schooner off the coast of Maine? Absolutely.

And in 2019, I went sailing again, this time with my best first mate, Nathan!

Table of Contents

All about the Best Maine Windjammer Cruise: The Schooner J&E Riggin

We sailed on the J&E Riggin , a 3-masted schooner built in 1927. The excitement begins even as you board the boat, because it’s unlike anything you’ve traveled on before.

You immediately get a sense of luxury-meets-antique; while the boat is nearly a century old and boasts many original features, it’s sparkling and modernized in all the right ways. The decks, especially where passengers gather, are made of a gleaming, vibrant wood.

The boat itself is dressed in red and blue—a truly classic Maine sailing vessel. And there are plenty of comforts of home, including insanely delicious meals.

On the first night, we stowed our luggage in our cabins below decks and met the captain and crew. We were briefed on our daily schedule and learned what our week aboard the Riggin would look like. We also learned a few essentials, including how to flush the toilets (very important!)

That initial evening, I felt a little nervous. I didn’t know how I would feel during the trip. I’d never spent that many days on a boat. Would I be seasick? What if I didn’t like the other passengers? Would my cabin feel claustrophobic?

I’ll admit, the unknown can be daunting, and I’m a person who gets a little anxious. As it turns out, my fears were unfounded and my nerves quickly calmed.

A historic lantern sits on wood surrounded by other small artifacts, like journals and phones.

By trip’s end, I could say without a doubt that the experience was fabulous, and above all, it was something really special and memorable.

But I can also surmise that all cruises offered are likely vastly different. No two journeys are the same, and that’s part of what makes this so amazing. So, while your experience will doubtless be its own magical time, if you’re thinking of going on a sailing cruise in Maine, I’d love to tell you just a bit of what you can expect on this adventure.

Maine is Gorgeous

First of all, if you’re going on a schooner cruise in Maine, you probably already know that the Maine coast has some of the most spectacular scenery. With that, you will not be disappointed.

The Penobscot Bay, where the J&E Riggin sails, is breathtaking. During the trip we were constantly passing islands of all sizes and descriptions. Rocky coasts, pine-covered hills, and even treeless islands where the seabirds gather.

Our cruise took us past a half dozen or more lighthouses, which is definitely a highlight of traveling in Maine.

White and black lighthouse sits on the coast in the distance; the foreground features a serene body of water under a grey sky.

As you sail on your Maine schooner, you’ll spend a lot of time gazing out at the blue waters of the Atlantic Ocean. Luckily, it’s incredibly beautiful. The meeting of the sea and sky, interrupted only by the gentle waves and the occasional porpoise or seal surfacing, is a hypnotic and peaceful sight.

Large body of water under a blue sky with a white boat floating on it in the distance.

You’ll Get Used to Everything Very Quickly

I have mentioned that I was slightly nervous my first night aboard the boat. My primary misgiving was the cabin. They are admittedly….a bit snug. I was sharing with Nicki and I took the top bunk. Our beds were wedged into the wall, and though we had plenty of storage space for our things, my initial reaction was that I was not looking forward to sleeping there.

But my worries quickly evaporated. It’s amazing how quickly a person can adjust to a new environment and a new routine. The cabins were ultimately extremely cozy.  With a comfortable bed, a warm light to keep you company while you read under the covers, and the sound of the sea outside your window, you sleep like a baby.

And you don’t spend much time in your cabin anyway. Nearly all your time awake is spent up on deck relaxing, chatting, dining, and sailing.

Aside from the accommodations, there are a few other unique features of schooner life to adapt to. But again, you adjust so quickly. The bathrooms on the ship are known as “heads” and they require a system of pumping to flush them. This must be done every time you use the head.

Don’t worry. It soon becomes second nature. (Now that I’m home, I find a self-flushing toilet to be a thing of WONDER).

A vase of flowers on a table in the foreground. The distance shows a person peering out to the water.

You’ll also have to share a single shower with all other passengers aboard. But again, this is no problem. When you want to rinse off, the crew can turn on the hot water and you can enjoy a pleasant shower in one of the heads. Most passengers are happy to shower just once while onboard (which is what I did).

The remainder of the time, let the sea be your natural cleanser! Hop in for a refreshing swim in the saltwater. You can also pack some essentials like dry shampoo and baby wipes—more on that later.

You Can Sail a Boat

While I still think sailing seems incredibly complicated, this Maine sailing trip taught me that—if you work as a team—anyone can help sail a vessel!

A wooden boat in a body of water.

Each day, when the crew of the Riggin raised the sails or heaved the anchor, they asked for volunteers. I never volunteered for the anchor raising…grown men seemed to quiver in their boots after that arduous task. But I did help out with raising the mainsail a few times.

Together, we all stood on the port and starboard sides of the deck and pulled the ropes hand-over-hand to lift those incredible, huge sails. It was rewarding work and it really makes you appreciate just how many “hands on deck” are necessary to help keep a boat afloat.

A person in a boat on a body of water.

Each Day is an Adventure

Because sailing relies so much on the wind, each day dawns with a somewhat unexpected itinerary. Though Captain Jon has a plan in mind, the Riggin often ends up “where the wind takes it.”

This is one of the most enjoyable aspects of the windjammer cruise. Every day will include some sailing as you make your way to your next stop.

Nearly every day gives you a chance to walk ashore, too. On our cruise, we stopped at Warren Island State Park, where we had our traditional lobster bake, as well as the town of Castine, which we were able to explore for a few hours.

You can expect to see a lot of the Maine coast and the Penobscot Bay on a schooner trip on the J&E Riggin. Wake up each day ready and hoping for an adventure and I’m pretty sure you’ll get your wish.

A sunset over a body of water.

The weather can be unexpected, too. But even rainy days can turn into beautiful nights, and in any situation, the crew works hard to keep you comfortable. Honestly, having a bit of a storm at sea can be kind of fun.

Wildlife is Everywhere, Keep Your Eye Out for It

Maine is a great place to spot some of God’s most amazing creatures (moose, to name just one), and the coast is no different. We saw porpoises, eagles, osprey, and my personal favorite, seals.

Blue lake by the rocky shore with trees.

Wildlife can appear at any time, and it’s usually when you least expect it. I found that just looking out at the water was the best method. Seals and porpoises are constantly popping up, sometimes fairly close to the boat. If you stay patient and keep your eyes open, you’ll almost certainly be rewarded with some Maine wildlife sightings.

You Will Be Eating Like a King (or Queen)

Before departing on our Maine windjammer cruise, we heard multiple times how fantastic the food was going to be. Those were words of truth! My goodness, we ate like royalty on the J&E Riggin. Every breakfast, lunch, and dinner was out of this world.

Foot sitting on a wooden table, featuring bread, potatoes, and salad. Boats floating on the water can be seen in the distance.

We had pastries for breakfast, homemade pancakes with a choice of three flavorful syrups (Maine blueberry available of course) and a hearty vanilla oatmeal one morning. There was fresh coffee every day. Home baked bread. Dinners ranged from Asian inspired rice bowls to hearty beef rubbed with herbs de Provence. Incredible deserts every evening, including peach cobbler, creme brulee, and a chocolate tart.

Aerial view of desserts in a bowl on a wooden table.

One of the highlights is the traditional lobster bake. The whole group heads ashore to cook up some fresh-as-can-be Maine lobster. The result is both delicious and visually beautiful! Along with corn on the cob, paella, fresh fruit, and s’mores for dessert, it’s the perfect summer meal.

Person shucking corn on a wooden table.

The cruise is BYOB, so bring along your favorite beverages to enjoy while onboard. There are lots of great Maine beers, ciders, and wines you could choose from if you want something local.

Your Shipmates Become a Bit Like Family

I think one of the most special things about a schooner cruise is the people you meet. There were passengers from all over the US, and it was a joy to chat with each of them.

I also really enjoyed interacting with the crew, and most of all with Captains Jon & Annie. These two are the owners of the vessel and the creators of the wonderful schooner experience aboard the Riggin. Jon is the ship’s captain while his wife Annie prepares the gourmet meals down in the galley. They are both aided by a crew of young, energetic people who were such fun and kind souls.

A group of people in a boat on a body of water

The J&E Riggin truly is a family affair. On the last night, Annie, Jon, and their daughter Ella, who was a crew member, entertained us with music and singing.

As we swayed in the falling darkness, the light of the lanterns gently illuminating our faces, we listened to the clear sounds of their voices bringing us traditional seafaring tunes. It was beautiful and sort of haunting, but I could see that every passenger relished the moment.

I can honestly say that this is one talented family, between sailing, building, cooking, music, writing, and even art.  It’s really special to get to know Annie, Jon, and the rest during those few days aboard the schooner. You can’t help but bond with one another through the experience.

A group of people on a boat with water in the distance.

Maine Windjammer Cruise Packing List

If you’re sailing in Maine, there are a few things you’ll want to be sure to bring. Summer in Maine can be warm, but out on the boat, the temperatures are often 20 degrees colder than onshore. Combine that with brisk winds and nighttime temps and you’re basically going to 100% need a jacket!

We went out on some super hot days and I still had to don my sweatshirt several times. I highly recommend bringing items of varying thickness so that you can layer (and un-layer) as need be. Aside from that, pack for practicality and comfort. Here’s what I suggest you pack:

  • Functional clothes you can layer
  • Dramamine or other anti-seasickness medication
  • Cleansing wipes
  • Dry shampoo ( this one’s my fave)
  • Hair elastics
  • Binoculars (so you can spot all the wildlife)
  • Sweater or sweatshirt ( this one is appropriate)
  • Waterproof jacket or windbreaker ( this jacket is currently the #1 bestseller for men)
  • Comfortable shorts/pants
  • Sandals with backs or boat shoes
  • Personal flashlight
  • Portable charger (you probably won’t use a phone much on the trip, but if you’re taking a lot of photos, bring a battery backup . This will come in handy on other trips, too). A solar one is a great idea!
  • A book to read
  • Small container for jewelry

It’s also wise to bring sunscreen and other toiletry items, but the boat also has plenty of these on board, so if you forget about an item, don’t worry.

How Much Does a Maine Windjammer Cruise Cost?

There are actually several different ways you can get out on a windjammer cruise in Maine! You don’t have to go on a multi day windjammer cruise to get a taste of Maine windjammer life. Check out these Maine windjammer cruises below!

Maine Windjammer Tours

Windjammer classic sunset sail.

This incredible Maine windjammer sunset cruise sails out of Camden Harbor, and it’s a great option for those who don’t want to commit to a multi day adventure at sea! This windjammer tour is about two hours long with cocktails available for purchase on board, so this would be a very cool idea for a date night at sea!

Click Here to Check Prices & Book!

Portland Tall Ship Cruise on Casco Bay

This Portland Tall Ship Cruise on Casco Bay is perfect for all ages. Just two hours long, you’ll sail from Portland, Maine on Casco Bay aboard one of three historic wooden windjammers. Snacks and beverages are BYOB, so come prepared!

2-Hour Windjammer Sailing Trip in Maine with Licensed Captain

Departing from Bar Harbor, this two hour windjammer sailing trip takes you through beautiful Frenchman Bay in Maine, allowing you a chance to take in the gorgeous Acadia National Park views from the sea! There are beverages for sale onboard and if you opt for the sunset sail, there’s even a live musician on board!

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  4. Windjammer Barefoot Cruises

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  5. Windjammer Classic Sunset Sail 2024

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  6. Why You Should Try a Windjammer Cruise

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COMMENTS

  1. Sailing Cruise Schedule

    2024 J. & E. Riggin Sailing Dates. PLEASE NOTE: Links to trip particulars will show information that reflect the current sailing season. Once the current season ends, the next year’s schedule will be updated with proper dates, instructors, and details. Available Promotion (s): Book your 2024 trip before February 1, 2024 for a 5% early booking ...

  2. MAINE WINDJAMMER CRUISES

    MAINE WINDJAMMER CRUISES. 2024 SAILING SCHEDULE. MERCANTILE. PRE-SEASON. SPECIALS. Best Value: Great Winds, Long Days & Uncrowded Anchorages. SIX-DAY TRIPS $1,300. Sun eve to Sat. THREE-DAY OPTIONS $875. Sun eve to Wed Wed eve to Sat . June 02. June 02. June 05 New Moon. June 09. June 12. June 16. June 19 Full Moon. June 23 June 23 June 26.

  3. Windstar Cruises

    Windstar Cruises | The World's Best Small Ship Cruise Line. New Experiences at The Brando. Private Villas. Learn More →. Your Greek Odyssey Awaits. Let Windstar be your guide. Explore Now →. Discover Iceland. Sail to the land of fire and ice. View Voyages →. Award-Winning Voyages. Find out what sets us apart. Learn More →. Tahiti Redefined.

  4. Island Windjammers

    May 26 - June 7, 2024 Leeward + French West Indies Home port: Rodney Bay, St. Lucia + Philipsburg, St. Maarten Visit a selection of: Anguilla | Antigua | Dominica | Guadeloupe | Iles des Saintes | Martinique | Montserrat | Nevis | St. Barths | St. Kitts St. Lucia | St. Maarten June 9 - 21, 2024

  5. Sailing on a Maine Windjammer Cruise: Everything you Need to Know

    Amy Hartle. Considering sailing on a Maine windjammer cruise? There is absolutely no better way to experience the coast of Maine. In this guide, we’re going to tell you all about what to expect on this fabulous Maine sailing trip. The best Maine windjammer cruises involve sailing on a traditional schooner out of Rockland, Maine.