Island Hop from Puerto Rico to Saint Barths on This Luxury Yacht Cruise

Kick off your incredible week by taking one of plenty of flights from around the world to San Juan, Puerto Rico. If you have some advance time on the island before your ship embarks in the evening, stroll the streets of Old San Juan, a UNESCO World Heritage site. Admire the paintings of Jose Campeche and Enoch Perez at the Museo de Arte de Puerto Rico or try local favorites like mofongo (mashed plantains) or arroz con gandules (rice with peas). Save room for a delicious dinner on the yacht.

Spend the morning on Culebra Island, known for its active reef and more than 20 marine life-filled cays. Known as Cuna del Sol Borincano (Cradle of the Puerto Rican Sun), the island is a favorite of nature lovers with its National Wildlife Refuge and designation as an Important Bird Area. Look out for sea turtles and colorful reef fish in the waters and birds like the masked booby and Sandwich tern in the sky. Anyone simply wishing to relax on some of the softest white sand in the Caribbean should visit Flamenco Beach, a horseshoe-shaped bay that often lands on “best beaches of the world” lists.

The Commonwealth of Puerto Rico consists of 143 islands and cays, islets, and atolls. After the morning in the waters of one sparsely populated island, the afternoon is for Esperanza, a bustling waterfront town on another island, Vieques. Along el Malecon (the Strip), you’ll find gift shops and a spectrum of food options, from low-key cafés and burger joints to daily menus featuring local angler’s catches. (Look up from your plate to appreciate the colors of the fishing boats nearby.)

Those interested in the island’s history, first inhabited by Indigenous people of the Americas 1,500 years ago, might want to check out the Vieques Conservation and Historical Trust, a small but fascinating museum. For more beach time, walk to Sun Bay, a balneario (public beach) about a half mile east of Esperanza.

Some island lovers make the mistake of skipping St. John in the U.S. Virgin Islands (USVI) because it has no airport. With Emerald Cruises, you can begin the morning in Cruz Bay, the restaurant and visitor hub of the island, four miles east of St. Thomas. Stroll through the pedestrian-friendly downtown, stopping at Wharfside Village for local shops. Head to Bajo El Sol Gallery, an art gallery in the Mongoose Junction shopping center, which is also home to a bookstore and rum bar.

For a great view, hike along the Lind Point Trail that begins near the USVI National Park Office and continues for a mile of incredible views and access to beloved beaches like Honeymoon Beach and Salomon Beach. Open-air taxis available for a fee can take you to famous beaches along the island’s northern coast, like Trunk Bay, Cinnamon Bay, and Maho Bay. (Pro tip: Trunk and Cinnamon offer gear rentals and snack bars.) By evening, enjoy the scenery for the approximately 35-minute sail to Jost Van Dyke, the smallest of the four major British Virgin Islands, at three square miles.

Many refer to the small British Virgin Island (BVI) of Jost Van Dyke as “the last Virgin Island” because it maintains the look and feel of a pristine destination. White Bay Beach, a secluded white-sand beach, is popular among travelers who return year after year for its close-to-shore reef and lively bars. Soggy Dollar Bar invented the painkiller cocktail in the 1970s, and Corsairs Beach Bar & Restaurant has a following among pizza lovers.

In the mood to explore? Head to the northeastern side of the island for a geological marvel known as the Bubbly Pool or, as some locals call it, “Mother Nature’s jacuzzi,” where a natural foamy pool forms from waves crashing between boulders. It’s a 20-minute hike from Foxy’s Taboo, where you might see goats, pelicans, and other local flora and fauna. On the way back, toast to your trip at Foxy’s with a Sly Fox (Firewater Rum, margarita mix, and bitters) or White Van Dykian (dark rum, Bailey’s, and Kahlua).

The island of Sint Maarten (or Saint Martin) has been home to two nationalities since 1648. The north is part of the French Republic as an overseas collectivity, and the south is one of four constituent countries of the Netherlands. Begin in Phillipsburg, an easy-to-explore, lively port town with Dutch and Caribbean influences. Feast your eyes on the iconic Courthouse on Front Street (where you’ll also find ample duty-free shopping); the bright colors of Old Street, which is full of local art galleries; and Walter Plantz Square with its gingerbread-inspired architecture.

Cinephiles might enjoy the Yoda Guy Movie Museum, featuring relics from film classics like The Terminator and The Maltese Falcon. After a morning of discovering the town’s diverse offerings, visit the Guavaberry Emporium, a specialty shop featuring the island’s national liquor. Follow it with a stop at one of the many restaurants for Dutch and French food. Come evening, set sail southeast to Gustavia, Saint Barthélemy, a 9.7-square-mile volcanic island in the French West Indies.

Originally called La Carénage, the city of Gustavia on St. Barths was renamed in 1784 to honor King Gustav III of Sweden. Today, it’s known as one of the most beautiful (if tiny) Caribbean capitals. You can see the entire area in a day, so don’t rush between the 17th-century Fort Karl, the Gustavia Lighthouse, and the many duty-free boutiques. Shell Beach is a short walk from town and, as its name suggests, is home to a seemingly endless number of shells.

Many fine-dining restaurants await in St. Barths, from L’Isola, a seafood restaurant, to Quarter Kitchen and Cocktail Lab, the island’s only pan-Asian gastropub. Or simply dine on the yacht for a singular view and fewer crowds with gentle waves lapping at the ship.

Nicknamed the Emerald Isle of the Caribbean, Montserrat is a volcanic island full of lush rainforest that’s said to resemble the Irish coastline. (Or perhaps it’s a nod to the island’s many residents with Irish ancestry.) The island had a legion of famous fans, including legendary producer George Martin, who set up his Air Studios Montserrat on the island and brought in recording artists like Eric Clapton, Little River Band, and Paul McCartney.

The Little Bay Port Development Project has begun work on a new town and port, where the yacht will dock today. Visit the Montserrat Monastery and the 12th-century La Moreneta (known as the “Black Madonna” statue). Those wanting another view can take the Funicular de Sant Joan to an observation point and hike to Sant Jeroni, the highest point on the island. End the day with British cuisine at the Attic or the local specialty of “goat water,” an herb-flavored goat stew.

Your week comes to a close in St. John’s, the largest city in Antigua. Those not quite ready to go home can book extra tour time with the Shore Excursion Manager. The city has plenty to do, from visiting Betty’s Hope, a historic sugar plantation, to getting in last-minute duty-free shopping.