Puerto Rico City Skyline from San Cristobal
Puerto Rico City Skyline from San Cristobal


Cruise out of San Juan, Puerto Rico to the most exotic isles in the region

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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