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San Juan, Puerto Rico

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Cruises from San Juan, Puerto Rico offer a magical blend of natural island charm and man-made wonders. Historic San Juan, once nothing more than cobblestone streets and the distinctive architecture of the Spanish who founded it, is now a modern world capital. And, as you’ll see on Carnival’s cruises from Puerto Rico, it’s kept these classical features! Among the peaceful shaded courtyards and commanding colonial fortresses of El Morro and San Cristobal, urban explorers will find a cosmopolitan city of wide boulevards, lively cafés, highly-regarded galleries and designer boutiques… not to mention gold-sand beaches and nearby rainforest jungles. San Juan, Puerto Rico is where the old world meets the new — and you can enjoy them both when you choose one of our cruises from San Juan.

• Castillo San Felipe del Morro (a.k.a. “El Morro”) features amazing history and the best view of the San Juan harbor.
• The Bacardi distillery ® spans 127 acres of land, and over 100 years of history.
• Vieques is an island's island — literally, featuring amazing beaches and found off the coast of Puerto Rico.
• Munch on mofongo , a fried plantain delicacy, a staple of menus throughout San Juan.

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Your Caribbean dream begins in San Juan's fiery scene

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A tapestry of culture and sun

Come for the warm weather and beach splendor; stay for the cultural heritage, laid-back vibes, and added adventures — from the thrills of ziplining to tasting different types of rum, uncovering eye-catching street art to giving into reggaeton.

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Explore Dominica's wilds, Cartagena's history, St. Maarten's charm, and St. Vincent's heritage — with late stays on our 7 to 11-night Caribbean voyages, you can dive deep into each destination's culture, cuisine, and unforgettable experiences.

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San Juan • Tortola • Philipsburg • Bridgetown • Fort-de-France • Castries • Basseterre

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Say goodbye to customs hassles and long layovers because jetting off to San Juan is a breeze for US-based Sailors. With direct flights to Luis Muñoz Marín International Airport, you’ll land straight into vacation mode. Your gateway to adventure begins at Pier 4, Paseo Concepción de Gracia, Old San Juan, PR 00901.

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"This cruise was literally the best vacation we ever went on. Our cabin was spacious and the crew was amazing. The shows were unique and entertaining. The drinks were delicious and it was awesome every bar had different main cocktails so you could try new things. I highly recommend it!"

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"This was my first cruise, and what an amazing time it was! The crew was amazing. The food was amazing! I love the places scattered around the ship to eat. Especially The Galley. Great vibe onboard. You can do as much or as little as you want to."

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"Overall everything was an amazing experience; the staff always made sure we were good and super helpful. I would recommend anyone to this cruise line over any other one. I think that you are definitely getting your money’s worth in value, in every aspect of the meaning."

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San Juan, Puerto Rico

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Founded in 1521, San Juan's picturesque cobblestone streets, plazas and chapels reflect its Spanish heritage. But the second oldest city in the Americas also boasts fine beaches, lush rainforests, verdant mountainsides, imposing forts and a lovely tropical climate. Looking for a cruise to San Juan? Read all about why you should cruise from San Juan .

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Cruises to & from San Juan, Puerto Rico

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Beautiful beaches, majestic mountains, historic sites, culinary experiences, and outdoor adventures—discover the many sides of Puerto Rico on a cruise from San Juan. The 100-mile long island is packed with a diverse array of experiences, from spirited salsa music to serene coral reefs, 16th century UNESCO World Heritage structures, and pastel buildings lining cobblestone streets. 

On a Caribbean cruise from San Juan, you’ll explore other enticing tropical destinations aboard one of our award-winning cruise ships. Lounge on the pristine beaches of Barbados and Aruba. Taste local rum or hike up a volcano in St. Kitts. Experience Bonaire’s famed dive sites and Curaçao’s historic Willemstad. Unwind in paradise in complete luxury with Celebrity Cruises. 

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Top destinations on cruises from san juan, abc islands.

The Caribbean islands of Aruba, Bonaire, and Curaçao are collectively known as the ABC islands. From luxurious white sand beaches and turquoise seas to spectacular diving sites and exotic animal encounters, the ABC islands offer something for every vacationer. Enjoy a guided horseback ride along the north coast in Aruba. Explore Bonaire’s renowned marine life from a glass-bottom kayak, or enjoy a two-tank scuba dive in the Caribbean’s top-ranked dive location. Take part in a hands-on cooking class with a local chef and learn how Caribbean ingredients impart an island flavor to dishes in Curaçao.

Visit one of the most spectacular natural wonders in the Caribbean—Harrison’s Cave. Descend deep into the cavern on a tram, where you’ll see incredible stalactite and stalagmite formations, bubbling streams, tumbling cascades, plunging waterfalls, and emerald pools. Embark on a guided safari adventure into the Wildlife Reserve, home to the free-roaming green monkeys, a rare sight outside of West Africa. Explore the island’s most beautiful locations on a four-wheel-drive vehicle. Or enjoy a spectacular sunset cruise, complete with a premium open bar and delicious hors d'oeuvres. 

The two-island nation of St. Kitts and Nevis has it all—a rich history, lush rainforests, soft sand beaches, and even a majestic volcano. Hike a beautiful rainforest to reach the crater of a dormant volcano and be rewarded with breathtaking views on a rugged island tour. Sail along the gorgeous coast of St. Kitts in a sleek catamaran, then jump in the ocean for a snorkel adventure. Or, take a day trip to Nevis, the birthplace of Alexander Hamilton, and explore the history museum with a break for lunch. 

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Why Sail from San Juan with Celebrity Cruises

On our cruises from San Juan, explore some of the less-traveled Caribbean islands on an unforgettable seven-night itinerary. Be transported to the world’s most unforgettable destinations in spectacular style. Reserve a beautiful stateroom or stay at The Retreat, our luxury vacation experience, where you’ll have a spacious suite that includes exclusive access to a private sundeck, restaurant, and lounge.

Throughout your journey, savor delicious dishes from menus crafted by our Michelin-starred chef. Enjoy revolutionary entertainment unlike anything else at sea. Discover new ways to look and feel your best at The Spa and Fitness Center.

San Juan Port Facilities & Location

Cruises that call in San Juan for a day conveniently pull into port right in the heart of Old San Juan. The Old San Juan Cruise Pier has a trolley stop, taxi ranks, and many places to shop and dine just steps away. If you’re embarking on one of the cruises from San Juan to the Caribbean, you’ll depart from the Pan American Pier, located in the Isla Grande neighborhood across the Cano de San Antonio bay from Old San Juan. The cruise terminal has a parking lot, taxi rank, and an air-conditioned lounge inside. If you’re heading straight to the airport after your cruise ends in San Juan, expect a 20-minute cab or shuttle ride between the cruise terminal and San Juan airport.

Top Sights and Attractions in San Juan

Castillo san felipe del morro.

Trek up the long sidewalk leading past the gorgeous green lawns that stretch out on either side of Castillo San Felipe del Morro, commonly referred to as El Morro. The lawns provide a gorgeous base to the stately standing fort at the top of the gently sloping hill, with the ocean sparkling all around it. Explore the fort’s old sleeping quarters, dungeons, and ramparts. Informational signs spread out around the fort will enlighten you about the history of El Morro and how it played a strategic military role for many centuries.  

Cathedral of San Juan

The beautiful Cathedral of San Juan is situated next to a pretty little park adjacent to some of the most charming streets in Old San Juan. In addition to its lovely setting, the Cathedral of San Juan is prominent for being the second-oldest cathedral built in the Americas and the burial site of Juan Ponce de Leon. 

Raices Fountain

Located within a light-filled square in Old San Juan, the impressive Raices Fountain is adorned with statues reflecting Puerto Rico’s cultural influences: the Tainos, the Spaniards, and the Africans. The monument, whose name means “roots,” acknowledges Puerto Rico’s vast history and heritage.

Learn More About San Juan Shore Excursions

Top things to do in san juan, walk around old san juan.

Be sure to leave time in your schedule to wander around Old San Juan, an area filled with colorful buildings, pretty plazas, and small parks situated alongside cobblestoned streets. It’s also home to some of San Juan’s most beloved sites, including two separate forts, cathedrals, and iconic statues. 

Mofongo and Mojito Experience

Immerse yourself in the history, culture, and cuisine of Puerto Rico with a multi-faceted tour that takes you on an expertly guided walk through Plaza Darsenas, the bustling Princess Pathway, the impressive San Juan Cathedral, and Old San Juan. Then, you’ll meet with a chef who will teach you how to make mofongo, a favorite dish in Puerto Rico. Afterward, sit down to a delicious three-course dinner accompanied by a refreshing mojito. 

Lounge on Beautiful Beaches

San Juan is home to soft sand beaches in shades of white and gold, lined by the turquoise hue of the Caribbean Sea. The beach ambiance you’ll encounter differs quite a bit depending on what beach you visit since some are laid back while others have more of a party vibe. The popular beaches of Isla Verde and Condado offer both relaxation and fun in the sun, with spots where you can rent lounge chairs and water sports equipment, and even get an oceanfront massage.

What should I eat in San Juan?

Puerto Rico has often been called one of the best Caribbean islands for foodies, and the focal point of all that delicious cuisine is San Juan. Try some tapas at a local cafe, or go all out with a waterfront dining experience at a fine restaurant. At some local restaurants, you’ll get to hear traditional music and watch dance performances during your meal. The can’t-miss food item to try in Puerto Rico is mofongo , a side dish that accompanies most meals made from fried green plantains mashed up with salt, olive oil, and garlic. For drinks, don’t miss some locally distilled rum or a glass of sangria. 

What’s the culture and history of San Juan?

Puerto Rico is an unincorporated territory of the United States. Its location in the northeastern Caribbean near the Dominican Republic and the Virgin Islands gives it a mix of Caribbean, American, and European influences. Adding to that cultural background is the history of the indigenous tribes who once lived here, African slaves who were brought to the island, and the colonial past that brought the Spanish, who built great forts and settled the town of San Juan in 1521. 

Today, you’ll find a city with a focus on the future while still striving to preserve its own unique culture of dance, music, cuisine, and folklore. Travelers on cruises from San Juan or visiting San Juan as a port of call will find that tourism is a big part of the economy and will be charmed by its residents, who are known for their warm hospitality to visitors. Behind the scenes, however, you’ll find one of the most robust economies in the Caribbean, which is largely influenced by the industries of service and manufacturing. Agriculture also plays a role in Puerto Rico’s economy, though not as much as it once did. 

Where can I go shopping near the San Juan cruise port?

Old San Juan has a plethora of souvenir shops located throughout the town. You’ll find typical souvenirs mixed in with locally made handicrafts. For a fun souvenir from San Juan, pick up one of the tourist-favorite Panama hats. Though not within walking distance for cruisers stopping in San Juan for the day, those taking one of the cruises from San Juan and flying in early will enjoy taking a stroll down Ashford Avenue in Condado, a part of New San Juan with a variety of boutiques and luxury stores. Plaza Las Americas, the largest mall in the Caribbean, has many popular brand name stores. 

How can I get around San Juan?

The bus system in San Juan stops at all the major attractions and is an affordable way to tour the city, both in Old San Juan and beyond to the neighborhoods of Condado and New San Juan. Old San Juan also has a free trolley service that visits many of the top sites. Look for the marked trolley stop signs and wait for the next one to arrive, which typically doesn’t take long as trolleys are frequently running. There are three different routes and two types of trolleys to choose from: open-air and enclosed with air conditioning. Taxis are also easy to hail in San Juan, where they line up outside the cruise terminal or in ranks around the city.

What are the local currency & tipping customs?

The official currency in Puerto Rico is the U.S. Dollar. You’ll find ATMs all around the city dispensing dollar bills. Expect to tip what you’re used to in the U.S., which is typically 15% to 20% of the total bill. 

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7 Night Cruise to Around the World

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35 Night Cruise to the Southern Caribbean

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14 Night Cruise to the Eastern Caribbean

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The most memorable cruises don’t necessarily need to take place in the classic exotic destinations. Rather the contrary even, they often are in other, surprisingly different places. Cruises through Norway’s epic fjords or along the majestic coasts of Alaska, for example, are magnificent. Another cruise hub that may come as somewhat of a surprise is Boston, Massachusetts.

There are a large number of interesting itineraries and cruise destinations from Boston. We discuss the best cruises from Boston and associated destinations below.

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Cruising from Boston

A historically important harbor city, Boston is still a starting point for many fantastic excursions by boat. In fact, it’s one of the main cruise ship bases on this side of the North American continent. Below, we’ve listed some of the very best cruise destinations from Boston. You’ll notice that those destinations are as varied as can be, including everything from northerly coasts to tropical islands.

From Boston, you can sail north along the rugged New England and eastern Canadian coasts or to the tropical paradise that is the Caribbean. The city—one of the oldest in America—also is a great starting point for cruises across the Atlantic Ocean toward Europe. Plenty of options, in other words, so let’s check out some of the best destinations for cruises from Boston below.

1. Bermuda Cruises from Boston

Bermuda is yet another of those island destinations that are associated with beach vacations. The thing is, however, that Bermuda lies surprisingly close to many cities on the United States’ East Coast. You might think that Bermuda is also a Caribbean or at least tropical island, but it’s not, even though it is, in fact, part of the Caribbean Community. It lies off the Mid-Atlantic Coast of the United States, closer to North Carolina and even Newfoundland than to Puerto Rico and the Virgin Islands.

This relatively northerly location doesn’t mean that this is a chilly destination, though. To the contrary rather, Bermuda boasts beautiful beaches and wonderful weather. Bermuda is arguably the greatest cruise destination from Boston , just because it is so surprisingly close, yet has a completely different culture and climate. Bermuda is actually one of the favorite holiday destinations among New Englanders.

Cruises are about seven days long and offer plenty of time to explore this beautiful island, which, incidentally, is a British Overseas Territory. Things to do range from scuba diving in barrier reefs to playing golf on world-class golf courses, sampling spicy local cuisine and exploring the island on a scooter.

👉 Get a quote on a Bermuda cruise from Boston

2. New England Cruises from Boston

The coast of New England is among the most spectacular in the world. It may not be lined with towering cliffs or have amazing beaches with palm trees, but the beauty of New England’s coast lies in its simplicity, ruggedness and historic charm.

From the harbors of Connecticut to the yachts on the Rhode Island coast, from the coastal villages and beaches of Massachusetts to the rocky shorelines in Maine, there is a huge variety found in New England. Joining a cruise from Boston, you’ll find yourself admiring iconic lighthouses, typical New England harbor towns and picturesque islands.

Major ports of call on these cruises are Portland, Maine, a beautiful town consisting of a charming old town, stroll-worthy waterfront and a few fine lighthouses, and Bar Harbor, Maine, which is the gateway to stunning Acadia National Park.

👉 Get a quote on a New England cruise from Boston

3. Canada Cruises from Boston

You can add an extension to a cruise from Boston to New England and head further north into Canada. Lasting from one to two weeks, these types of cruises take in many highlights on the coast of eastern Canada, a region that’s much less visited than other parts of that vast country.

Departing from Boston, the trip might take you along the gorgeous New England coast, calling at Bar Harbor, Maine, before heading north to Nova Scotia. Destinations included in this memorable cruise are Halifax in Nova Scotia, Charlottetown on Prince Edward Islands (famous for its mussels), and the St. Lawrence River, Québec City and Montréal in Québec.

This is the perfect way to explore the eastern parts of Canada in a relaxed and convenient way. This cruise features mouthwatering seafood, epic coastal landscapes, picturesque fishing towns, fascinating history and, if you’re lucky, sightings of marine animals such as porpoises, seals and even whales.

👉 Get a quote on a Canada cruise from Boston

4. Caribbean Cruises from Boston

Nothing invokes images of the perfect beach getaway quite like the Caribbean. This region is almost synonymous with a lifestyle featuring upbeat music, coconut-based cocktails, hammocks and perpetual sunshine. It’s the absolute perfect cruise destination.

Cruising from one Caribbean island to the next is the stuff travel dreams are made of and you can experience it yourself by joining a cruise from Boston. These cruises from Boston typically travel south along the East Coast of the United States, calling at popular places such as Charleston, Miami, the Bahamas and various Caribbean towns and islands.

Once in the Caribbean Sea, the cruise takes you to iconic destinations including Puerto Rico, the Virgin Islands, Antigua, St. Maarten and several others. Some itineraries also include destinations on the continental coasts of the Caribbean Sea. Examples are Cancun in Mexico, Costa Rica, and Cartagena in Colombia. (Note that different cruises follow different routes and have different itineraries.)

If you really want to experience the Caribbean as a whole, as opposed to visiting just one island, a cruise is the one and only way to do that. The Caribbean islands are undoubtedly among the best cruise destinations from Boston.

What’s better than getting on board in Boston and letting the ship take you to sunnier places? These cruises generally last between nine and twelve days.

👉 Get a quote on a Caribbean cruise from Boston

5. Panama Canal Cruises from Boston

Panama Canal cruises from Boston are a great way to see some of the most beautiful scenery in the world. The cruise ships depart from Boston and sail down the east coast, into the Caribbean sea, and then through the Panama Canal. Depending on your voyage, you’ll have the opportunity to visit some amazing ports of call, including Colon, Cozumel, Half Moon Cay, Grand Turk, the Bimini Islands, and more.

One of the highlights of a Panama Canal cruise is, of course, the transit through the canal itself. This is truly an engineering marvel, and it’s an amazing experience to watch the ships being lifted up and down through the locks. You’ll also have the opportunity to learn about the history of the canal and its importance to world trade.

In addition to the Panama Canal, you’ll also get to see some of the most beautiful scenery in the world. The cruise ships sail through the Caribbean Sea, past lush islands and crystal-clear waters.

If you’re looking for a once-in-a-lifetime vacation, a Panama Canal cruise from Boston is the perfect choice. You’ll see some of the most amazing scenery in the world, learn about history and engineering, and have a truly unforgettable experience.

These are the five best cruises from Boston, Massachusetts. In all their variety, they offer pretty much everything you could possibly be looking for. Whether you’re after a sun-sea-and-sand vacation or a holiday focused on local cuisine or nature, you’ll definitely get to your preferred destination(s) on these cruises.

Cruises Out Of Visit Boston

Many of the world’s largest cruise lines stop in and depart from Boston, the main cruise hub of New England. These are the major companies that currently sail out of the Boston cruise port.

• Celebrity Cruises
• Holland America Line
• Norwegian Cruise Line
• Royal Caribbean
• Seabourn Cruise Line

About the Boston Cruise Port

The Boston cruise port is officially known as Raymond L. Flynn Black Falcon Cruise Terminal . The cruise port of Boston is in the heart of the revitalized Seaport District of Boston Harbor in South Boston. It is a modern cruising facility with two different terminals. One terminal is dedicated to ships visiting Boston as a port of call, while the other is specifically for departing ships.

Located only about one and a half miles from historic downtown Boston, just 10 minutes from Boston Logan, and close to both the I-90 and I-93 interstates, it’s a very accessible port for cruises to wide variety of destinations, as you could see above. Additionally, the cruise port is also served by the MBTA Silver Line bus service.

The Flynn Cruiseport of Boston receives hundreds of thousands of passengers in a typical year, either as visitors on cruises or people leaving on a holiday cruise from Boston.

Get a price on a cruise in this post

Born and raised in Belgium, Bram is currently based in the Pacific Northwest where he spends his days blogging, hiking, indulging in freshly roasted coffee and sipping craft beers. An experienced traveler, his… More about Bram R

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Interested in a cruise from Boston mass

We can certainly help you find a cruise from Boston. There are many great options, and Holland America just added a couple of itineraries. Give us a call at 1(800) 498-7245 or request a quote to get in touch.

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San Juan, Puerto Rico

Cruises from San Juan depart year-round. Old San Juan is rich in Spanish tradition, with iconic blue cobblestone streets and colonial architecture. This historic section of the Puerto Rican city is easily seen on foot, and cruise passengers can shop for handcrafted works, relax in a shaded park or tour El Morro, a 16th-century Spanish fortress overlooking the sea. New San Juan is distinctly elegant with lavish resorts, great restaurants and grand casinos. Visitors can enjoy an outing to El Yunque, the only tropical rain forest in the U.S. national forest system, or join in on shore excursions that include the likes of deep-sea fishing, snorkeling, diving and even kayaking on a bioluminescent bay.

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Princess Cruises offers Southern Caribbean itineraries from San Juan Puerto Rico in 2025-2026

Princess Cruises has announced its return to San Juan Puerto Rico , offering Southern Caribbean voyages with the Grand Princess ship from October 2025 to March 2026.

Puerto Rico's capital city provides a cultural and historical backdrop for tourists to explore before and after their cruises, with numerous attractions to discover. These 7-day roundtrip itineraries, which include more port visits than any other 7-day Princess Caribbean itinerary, will go on sale starting May 16th.

Originally planned for Australia, New Zealand, and South Pacific routes from Brisbane and Sydney , the Grand Princess will now embark on two alternating 7-night itineraries from October 12, 2025, to March 29, 2026. These new itineraries each feature stops at five distinct destinations, highlighting some of the top-rated Southern Caribbean locales - many of which are unique to cruises departing from Florida. Guests have the option to combine itineraries for an extended 14-day journey.

The 16-deck Grand Princess offers a variety of culinary experiences, signature Princess amenities like The Sanctuary/adults-only zone, Movies Under the Stars/outdoor cinema, and Broadway-style shows in the Princess Theater. Additionally, guests can enjoy a personalized vacation with Princess MedallionClass , featuring advanced technology such as MedallionNet (the best WiFi at sea), and convenient touchless services like food and drink delivery anywhere on board.

Furthermore, with Princess Plus and Princess Premier packages, guests can save over 65% on essentials such as gratuities, Wi-Fi, beverages, and more, enhancing the overall value and enjoyment of their cruise experience.

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Princess Cruises to Launch Voyages Out of This Caribbean Destination for the First Time in 10 Years

Starting October 2025, the cruise line will sail from San Juan, Puerto Rico on seven-day voyages on board the Grand Princess.

Courtesy of Princess Cruises

Princess Cruises will return to San Juan, Puerto Rico, next year for the first time in more than 10 years, sailing week-long voyages from the U.S. territory.

Starting October 2025, the cruise line will sail from the capital of Puerto Rico on seven-day voyages on board the Grand Princess . Princess will plan to sail these southern Caribbean voyages through March 2026, the company shared with Travel + Leisure.

The Grand Princess will sail two alternating itineraries, both roundtrip from San Juan. The first will include stops in Tortola, St. Kitts, Dominica, Grenada, and Barbados, while the second will include stops in St. Thomas, St. Maarten, Antigua, St. Vincent, and Barbados. Each will include a day at sea.

“Our return to San Juan after more than a decade not only reconnects our guests with a port rich in history and charm, but further expands the variety of departure points across North America that our guests can sail from,” Terry Thornton, the chief commercial officer for Princess Cruises, said in a statement shared with T+L. “Puerto Rico remains one of the fastest-growing destinations in the Caribbean and continues to attract new airlift from source markets across the U.S. as well as markets in Europe and South America, which makes it a great fit for Princess. Plus, there are many outstanding options to choose from for a great pre- or post-cruise stay.”

While on board the 2,600-guest Grand Princess ship, passengers can enjoy a mini golf putting course, indulge in afternoon tea, relax in the adults-only The Sanctuary, and more. The Grand Princess is the oldest in the company’s fleet , but underwent a major renovation in 2019.

Cruises from San Juan will go on sale on May 16, according to the company.

While Princess is making plans to return to San Juan next year, the company was forced to delay another 2025 debut when it pushed back the delivery of its newest ship , the Star Princess , by about two months. That ship is now expected to sail in the fall of 2025.

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Princess Cruises Returns to San Juan After More Than a Decade

Princess Cruises will return to San Juan, Puerto Rico, to offer Southern Caribbean cruises onboard Grand Princess from October 2025 through March 2026.

The 2,600-guest ship was originally scheduled to sail around Australia, New Zealand and the South Pacific. Instead, the cruise line is sending the vessel to the Caribbean. 

The 7-day itineraries will be available for booking starting May 16.

“Our return to San Juan after more than a decade not only reconnects our guests with a port rich in history and charm, but further expands the variety of departure points across North America that our guests can sail from,” says Terry Thornton, chief commercial officer for Princess Cruises. “ Puerto Rico remains one of the fastest-growing destinations in the Caribbean and continues to attract new airlift from source markets across the U.S. as well as markets in Europe and South America, which makes it a great fit for Princess. Plus, there are many outstanding options to choose from for a great pre- or post-cruise stay.”

Guests who sail aboard Grand Princess will have a chance to explore five destinations: St. Thomas, St. Maarten, Antigua, St. Vincent and Barbados. They can combine two back-to-back voyages to create a 14-day journey.

“We are excited to welcome Princess Cruises back home to the Port of San Juan,” says Carlos Mercado Santiago, executive director of the Puerto Rico Tourism Company. “This announcement underscores our commitment to cement San Juan as the leading homeport in the region, where guests can sail throughout the wonderful ports of the Eastern and Southern Caribbean. Furthermore, the sailings will help drive economic development for both Puerto Rico and our regional partners.”

Boston Cruise Guide > Cruise Destinations > Repositioning

Repositioning Cruises from Boston

You can get on a "repositioning cruise" from Boston in the autumn each year. Cruise ships sail out of this port in the warm weather months, so for the winter they have to move to another departure port. The move is called a "repositioning cruise". See the calendar of departures below.

Repositioning cruises are usually bargains, because one-way cruises aren't as popular as round-trips. Out of Boston you can take a cruise to a warm place like California, Puerto Rico or Florida. Spend a little extra time there, then fly home.

October 11, 2024: 10-night repositioning cruise on Celebrity Cruises . One-way from Boston to Fort Lauderdale (Florida). Visit Royal Naval Dockyard (Bermuda), Willemstad (Curacao), Oranjestad (Aruba) and Kralendijk (Bonaire).

November 9, 2024: 14-night repositioning cruise on Holland America Line . One-way from Boston to Fort Lauderdale (Florida). Visit Bermuda, St Thomas, St Maarten, St Lucia, Barbados, Curacao and Half Moon Cay (Bahamas). • 2024 departure: November 9.

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Princess Cruises Expands Caribbean Program with Return to San Juan Home Port

Grand princess to sail southern caribbean itineraries from puerto rico, visiting most ports of any seven-day caribbean itinerary.

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FT. LAUDERDALE, Fla., (May 7, 2024)  – Princess Cruises today announced its return to San Juan, Puerto Rico for a season of Southern Caribbean cruises onboard Grand Princess, from October 2025 through March 2026. This vibrant capital city of Puerto Rico offers rich history and culture with must-see attractions for Princess guests pre- and post-cruise. These seven-day cruises, which visit more ports than any other 7-day Princess cruise to the Caribbean, are on sale May 16.

“Our return to San Juan after more than a decade not only reconnects our guests with a port rich in history and charm, but further expands the variety of departure points across North America that our guests can sail from,” said Terry Thornton, chief commercial officer for Princess Cruises. “Puerto Rico remains one of the fastest-growing destinations in the Caribbean and continues to attract new airlift from source markets across the U.S. as well as markets in Europe and South America, which makes it a great fit for Princess. Plus, there are many outstanding options to choose from for a great pre- or post-cruise stay.”

Originally scheduled to sail Australia, New Zealand and South Pacific voyages from Brisbane and Sydney, Grand Princess will now sail two alternating, seven-night itineraries, with departures from October 12, 2025 - March 29, 2026. These new itineraries each feature visits to five different and unique destinations, including many of the most highly rated Southern Caribbean destinations—many of which are not available on 7-day cruises departing from Florida.

“We are excited to welcome Princess Cruises back home to the Port of San Juan. This announcement underscores our commitment to cement San Juan as the leading homeport in the region, where guests can sail throughout the wonderful ports of the Eastern and Southern Caribbean. Furthermore, the sailings will help drive economic development for both Puerto Rico and our regional partners”, said Carlos Mercado Santiago, executive director of the Puerto Rico Tourism Company.

Grand Princess Itineraries Sailing Roundtrip from San Juan:

Guests can choose to combine itineraries for an incredible 14-day voyage.

The 2,600-guest Grand Princess offers an array of culinary delights, signature Princess amenities like The Sanctuary and Movies Under the Stars, and Broadway-style productions in the Princess Theater. Plus, guests can enjoy a truly personalized vacation with Princess MedallionClass, featuring next-level technology with MedallionNet - the best WiFi at sea - food and drinks delivered wherever they are, touchless experiences and more.

Plus, enhancing the vacation value with Princess Plus and Premier inclusive packages allow guests to save over 65% on essentials such as gratuities, Wi-Fi, beverages, and more, providing added convenience and enjoyment for their journey.

Additional information about Princess Cruises is available through a professional travel advisor, by calling 1-800-Princess (1-800-774-6237) or by visiting www.princess.com .

Media Contacts

Contact information for members of the media

Negin Kamali, +1 661-753-1539, [email protected]

Briana Latter, +1 661-753-1538, [email protected]

About Princess Cruises

Princess Cruises is The Love Boat, the world’s most iconic cruise brand that delivers dream vacations to millions of guests every year in the most sought-after destinations on the largest ships that offer elite service personalization and simplicity customary of small, yacht-class ships. Well-appointed staterooms, world class dining, grand performances, award-winning casinos and entertainment, luxurious spas, imaginative experiences and boundless activities blend with exclusive Princess MedallionClass service to create meaningful connections and unforgettable moments in the most incredible settings in the world - the Caribbean, Alaska, Panama Canal, Mexican Riviera, Europe, South America, Australia/New Zealand, the South Pacific, Hawaii, Asia, Canada/New England, Antarctica, and World Cruises. The company is part of Carnival Corporation & plc (NYSE/LSE:CCL; NYSE:CUK).

Additional media information is available at princess.com/news

Not a member of the media? 

Contact us at: 1-800-PRINCESS (1-800-774-6237) or 1-661-753-0000

More contact information is available on our Contact Us page

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7 Night Cruise to Around the World

• You want a cruise with plenty of wow but on a smaller scale
• You appreciate bright, airy public rooms and lots of open decks
• You dislike the look and feel of the newest mega-cruise ships
• You need ziplines, thrilling waterslides or active diversions
• You want wall-to-wall entertainment; these ships are quieter

35 Night Cruise to the Southern Caribbean

• You want a high-quality cruise experience with classic touches
• You love live music; Zuiderdam's venues excel in this area
• You like your ships big and full of features, but humanly sized
• You crave vibrant nightlife; things wind down around 10 p.m.
• You want thrill-seeking amenities like waterslides or ziplines

11 Night Cruise to Canada & New England

• You want to sail on an intimate, former luxury cruise ship
• You don't care about the sails on Windstar's other ships
• You love relaxing on-deck and chatting with fellow guests
• You're prone to seasickness; these small ships can roll around
• You really like the idea of Windstar's hybrid sailing ships
• You need cabins and suites with real step-out balconies

41 Night Cruise to Around the World

• You want to have a floating boutique hotel with every comfort
• You place high value on good cuisine and consummate service
• You want an adult-centric cruise to interesting ports of call
• You want the glitz and glam of Oceania's newer, larger ships
• You tend to suffer from seasickness; this ship can move around

14 Night Cruise to the Eastern Caribbean

21 night cruise to the eastern caribbean, 21 night cruise to the southern caribbean, explore boston.

Cruises from Puerto Rico to the Caribbean

Priced per person, based on 2 guests. Est. tax/fees of $132 pp not included.

Priced per person, based on 2 guests

Priced per person, based on 2 guests. Est. tax/fees of $143 pp not included.

Priced per person, based on 2 guests. Est. tax/fees of $110 pp not included.

Priced per person, based on 2 guests. Est. tax/fees not included.

Priced per person, based on 2 guests. Est. tax/fees of $153 pp not included.

Priced per person, based on 2 guests. Est. tax/fees of $101 pp not included.

Priced per person, based on 2 guests. Est. tax/fees of $183 pp not included.

Priced per person, based on 2 guests. Est. tax/fees of $137 pp not included.

Priced per person, based on 2 guests. Est. tax/fees of $124 pp not included.

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THE BEST CRUISES FROM SAN JUAN, PUERTO RICO

Published on March 31, 2020

Amazing food, pristine beaches, rich history and culture — there are so many reasons why everyone should add Puerto Rico to their vacation list. That said, ask any savvy traveler and they’ll likely tell you that the best Puerto Rico vacations are cruises. Why? Because you can bundle multiple beautiful island destinations into one unforgettable getaway. San Juan’s cruise port is the perfect gateway to the entire southern Caribbean , home to some of the most exotic isles in the region. From stops at serene St. Kitts to lively Punta Cana, there’s no better way to level up a few days on the Isle of Enchantment than by setting sail on a cruise from San Juan, Puerto Rico. We’ve rounded up some of the most iconic destinations you can visit on a San Juan cruise, plus tips on how to maximize a few days before or after your sailing at this amazing departure port.

San Juan, Puerto Rico

Your southern Caribbean vacation begins and ends in sunny San Juan, Puerto Rico . No matter where you’re flying in from, it’s always a good idea to spend a few days here before or after your San Juan cruise. Make sure to dedicate some time to the city’s old town, famous for its quaint cobblestone streets lined with colorful colonial buildings, its balmy plazas dotted with bustling cafes and trendy cocktail bars, and its old city walls. Stop by the San Felipe del Morro and San Cristobal fortresses for a taste of the city’s rich history, then indulge in a day of sand, surf, and salty breezes at glitzy El Condado Beach or tranquil Flamingo Beach on Culebra Island, an easy ferry ride away. And once the sun goes down, sample San Juan’s famous nightlife — locals here will tell you that no matter where you are in the city, you’re never far from a great party.

King’s Wharf, Bermuda

A stop on most San Juan cruises to Baltimore and the New York area, Bermuda is a pastel-colored paradise. From its pink sand beaches to its brightly painted estates, every inch of this island is striking. If you’re into history, check out the Royal Naval Dockyard, where the stone structures date back to the 18th century, or Historic St. George’s, filled with four-hundred-year-old forts and homes. You can also stroll past the quaint boutiques and specialty shops through the charming town of Hamilton, founded in 1790, and now home to lots of boutiques and specialty shops selling local wares. If you’re a foodie make sure you try a dish of codfish with potatoes — you can order it the English way, with a hard-boiled egg, or the Portuguese way, prepped in tomato-onion sauce.

How to get there: you can cruise to King’s Wharf, Bermuda, from San Juan on a 6-night cruise to Cape Liberty, New Jersey onboard the Amplified Freedom of the Seas®, or on a 5-night cruise to Baltimore, Maryland onboard Enchantment of the Seas®.

Basseterre, St. Kitts

St. Kitts is the perfect island destination for nature lovers. You’ll find the best wonders here are underwater and in the jungles and tropical forests that thrive further inland. If you’re up to a 3,792-foot hike up Mount Liamuiga, you’ll be rewarded with breathtaking views of the surrounding land and sea. Prefer to take your adventure under the waves? There are plenty of incredible coral reefs located just offshore that are perfect for snorkeling and kayaking. And if you’re looking for a beach day that feels a world away from reality, hop on a thirty-minute ferry ride to St. Kitts’s sister island, Nevis, home to secluded golden-sand beaches and crystal-clear aquamarine waters. Take it from us — a stop in St. Kitts makes an unforgettable addition to your cruise from San Juan, Puerto Rico.

How to get there: you can cruise to Basseterre, St. Kitts from San Juan on 7-night southern Caribbean sailings onboard Freedom of the Seas® and Enchantment of the Seas®.

Kralendijk, Bonaire

If you love snorkeling and diving, you should definitely make sure you pick a San Juan cruise that has Bonaire on the itinerary. This dazzling southern Caribbean isle is nicknamed “Diver’s Paradise” thanks to its abundance of dive sites (there are 86 at Bonaire Marine Park alone), and its many coral reefs also lure snorkelers from around the world. If you’re more of a land-loving explorer, head to Washington Slagbaii National Park, which encompasses more than a fifth of the island. You’ll find all kinds of landscapes here, from sweeping sepia-toned deserts to thick mangroves and placid lagoons.

How to get there: you can cruise to Kralendijk, Bonaire from San Juan on 7-night southern Caribbean sailings onboard the Amplified Freedom of the Seas®.

Bridgetown, Barbados

This southern Caribbean jewel is a hub of culture, history, and wild beauty, and a must-visit destination for anyone sailing on a San Juan cruise. Most visitors kick off their stay with a stroll through the island’s bustling historic “Town,” as locals refer to it, but soon end up taking their adventure further afield to the rolling hills and emerald forests of the Barbados Wildlife Reserve, the sun-soaked shores of Carlisle Bay Beach, or the crystal-clear streams and pools of water inside Harrison’s Cave, an awe-inspiring system of limestone caverns located 170 feet below ground. Want to bring a little piece of the island home with you? Hit the stores along Broad Street, Bridgetown’s main avenue, and pick up some locally made rum cake (which islanders call “great cake”).

How to get here: you can cruise to Bridgetown, Barbados from San Juan on 7-night southern Caribbean sailings onboard Enchantment of the Seas®, Vision of the Seas®, and the Amplified Freedom of the Seas®.

All of these islands are top-rated destinations for travelers around the world, but they’re just a sampling of the incredible places you can visit when you choose a cruise for your Puerto Rico vacation. Cruise itineraries sailing from the San Juan cruise port also include stunning isles like Martinique, St. Thomas, Tortola, Curacao, and Aruba, just to name a few. What’s more, you get to start and end your vacation in one of the Caribbean’s most iconic destinations — vibrant San Juan, Puerto Rico, filled with countless wonders to discover. No matter which San Juan cruise you choose, you’re bound to have an unforgettable vacation.

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