Hunter Thompson wrote, “There is something fresh and crisp about the first hours of a Caribbean day, a happy anticipation that something is about to happen …” A tapestry of more than 7,000 islands, the Caribbean bursts with rugged adventures, shimmery coral reefs, spicy salsa beats and rainbow-colored homes all kissed by the sun and—perhaps—a splash (or two) of rum. Picking the right islands can be tricky, but this guide offers “happy anticipation” vibes for stress-free planning of your next trip.
Bienvenida (Welcome) to San Juan
You might come to San Juan for the tropical weather and the pristine beaches, but you’ll stay for the delicious smell of roasted pork, welcoming island hospitality, Spanish colonial townhouses and rich 500-year-old history. Your journey begins on the spectacular Isla Verde Beach, home of Fairmont El San Juan Hotel, an oasis situated on more than two miles of silky sands and crystalline waters.
Earn your sea legs by captaining a mini boat as you soak in the panoramic views and iconic sites of Old San Juan away from the crowds. Pro tip: Additional tours feature the mountainous views of El Yunque National Forest, the only tropical rainforest in the US. For a birds-eye view of the island and all of its wonders (perfect for travelers on a time crunch), take to the sky in a 10- to 15-minute private helicopter tour. As the sun sets over San Juan, let the stars and plankton guide you as you paddle through the rare Fajardo bioluminescent bay with a nighttime kayak tour.
For food-focused travelers, discover the blend of African, Spanish and Taino flavors in the comida criolla, pasteles and tostones at Deaverdura in Old San Juan, fall in love with mofongo at Casita Miramar (a local favorite) or enjoy authentic Puerto Rican flavors at Caña by Juliana Gonzalez. For a nightcap, follow the crowd to the unmarked speakeasy, La Factoria, that slings craft cocktails as masterful as the live salsa dancers.
Adventure-Lovers Need Apply: Welcome to Barbados
You may be inspired to write your own Rum Diary after visiting Barbados, aptly nicknamed the “Culinary Capital of the Caribbean” and the “Birthplace of Rum.” Rum-soaked dreams are made at St. Nicholas Abbey, the only local rum distillery to still grow and use its own sugar cane to craft its award-winning libations. Hop aboard their Heritage Railway for a 1-hour tour of the plantation fields and lush coastal grounds, pre- or post-rum tasting.
From rum tasting to nature bathing, tap into your moment of Zen at Coco Hills Forest, a 53-acre tropical forest off the island’s east coast. Self-guided tours allow you to hike, forest bathe, and picnic at your leisure. As you emerge rejuvenated, you may hear the sweet siren call of the ocean. Barbados rivals Hawaii for the dreamiest waves and ideal year-round tradewinds, making any time a good time for windsurfing, kite surfing or following in Kelly Slater’s wake at Soup Bowl, named the most consistent surf spot on the planet. You’ll also find Fairmont Royal Pavilion, an award-winning luxury retreat, located on its own private beach in St. James Parish, where celebrities often trade the California coast for this tropical west coast (aka the “platinum coast”).
To feed your post-hang ten appetite, head to PEG Farm and Nature Reserve for a farm-to-table lunch of pasture-raised meat, local produce, biodynamic wines and freshly squeezed juices. If you’re lucky enough to be in Barbados on a Friday, follow the mouthwatering smell of grilled seafood to an Oistins fish fry, where fried and grilled tuna, mahi-mahi and lobster await among live music, domino games and arts and craft vendors.
Get on Island Time: Welcome to Bermuda
While it’s not a Caribbean island, though often grouped with them, there’s something mysterious and alluring about Bermuda. It’s not just its paranormal urban legends, swashbuckling past or the fact that it’s the shipwreck capital of the world. To discover the island’s je ne sais quoi, follow the powdery pink sands to the “Pink Palace,” Hamilton Princess, a sandcastle-like oasis with nearly two centuries of history. It’s been a secret World War II intelligence center to Mark Twain’s regular haunt, which is why it’s nicknamed “the gem of the island.”
Discover every inch of the island’s 21 square miles by renting a Twizy, an electric two-seater vehicle that makes cruising around the island a figurative and literal breeze. Hike, swim and go cave-exploring at Tom Moore’s Jungle, the local name for Walsingham Nature Reserve and nearby Blue Hole Park on the island’s east end. Cap off your day of adventure with one of Bermuda’s famous fish sandwiches at Art Mel’s Spicy Dicy in Hamilton or Woody’s on Boaz Island. Pro tip: Ask for the “local fish” and the planter’s punch, a signature cocktail that’s not always on the menu but all the bartenders know.
Honor the island’s British traditions with afternoon tea at the Hamilton Princess or Lili Bermuda Perfumery, which also offers artfully crafted fragrances inspired by the island’s natural elements. On spring evenings catch the spectacular bioluminescent dance of the glow worms from Ferry Reach Park bridge or head away from the city lights to Cooper’s Island Nature Reserve for the clearest, year-round stargazing.
Stephanie Andrews has rock climbed in Malta, driven an ATV around Gozo, run the Dead Sea half-marathon, survived a Temazcal and traveled to more than 15 countries. Her work has appeared in Travel + Leisure, Food52 and Matador Network. When not eating her way through a city, she’s often writing about food.