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Pristine, untouched and unforgettable: There’s no other way to describe this natural park just off the northeast coast of St. Croix. Walking trails crisscross the expanse through frangipani and tamarind trees and cacti to beautiful beaches. Turtle Bay, on the western side, wows with its magnificent snorkeling; the protected waters and massive coral reef are home to more than 250 kinds of fish. Admission numbers are limited each day; advance booking is required.

I think the most appealing aspect of Old San Juan is the architecture and design of the city. Residential apartment buildings have been converted to designer boutiques or little B&Bs, and interior courtyards invite hungry guests to relax and unwind in the shade.... I’ve been to this area multiple times and still I manage to find a street I’ve never wandered down. Some are more popular than others, in particular Calle San Sebastian, which hosts eateries, bars, and shops, and Calle San Francisco. At the corner of this street is my particular favorite, Franky’s antiques. It’s in a four-story building, loaded with vintage goodies. There’s so much to see, one trip is not enough. If you want to shop, consider wandering all morning and into the early afternoon. You’ll be delighted by all the unique shops. Then, take a break at my favorite restaurant, Triana, for Spanish-style tapas and their famous sangria. It’s a must-stop place any time I’m in the old city. You don’t need a car to get around. Just park at one of the garages and explore by foot. There’s lots to see and do in Old San Juan.

Goldeneye, to be clear, is not an easy place to leave. The land—the former home of Ian Fleming, where he wrote each of the 14 James Bond thrillers that would cement his place in literary and cinematic history—sits next to the tiny town of Oracabessa, on the northern coast. A warm, blue-green lagoon curls from the ocean around a small island and then lets out into a bay. You can look one direction and see a jungle, then turn around and see pristine white sand.

Blackwell bought the property in 1976 as a vacation home and a space to entertain family and friends but later he decided to transform it. In 2016, Goldeneye debuted a jumble of new huts, arranged around a small cove, a short walk from Fleming’s house and the resort’s original villas. The huts vary in height, designed to capture cooling breezes and allow guests to forgo air conditioning. And, crucially, they’re much cheaper to book than the Villas. Which is key because, up until this point, if you wanted to plan a visit to Goldeneye, you needed to either know Blackwell personally or have the excess capital to shell out potentially five figures on a vacation. (Part of the resort’s enduring gravitational pull is that many of the celebrity guests check both boxes.) With the beach huts, Blackwell has expanded, once again, the ambition of his famous resort.

It would be hard to find a more idyllic spot for recharging than Naïa Resort and Spa, Placencia’s newest (and, we’ll say it, most comfortable) resort. Stay in your own studio, one-, two-, or three-bedroom beach house, all of which come equipped with floor-to-ceiling front windows, a kitchenette, a deep tub, and an outdoor shower (trust us: once you’ve had the luxury of an outdoor shower, you’ll never want to go back to the boring, indoor version). Every beach house is just that: a beach house. You’re never more than a short walk from the shores of the Caribbean Sea, and the Naîa’s watersports center can get you off the sand and into the water on a kayak or paddleboard. (While you’re there, ask for Stony, whose a pleasant man to talk to and the guy you’ll need to open a fresh coconut from one of the many palm trees on the property). The resort also staffs expert concierges, who can recommend the best tours, spa treatments, and in-town experiences.

The spa, as expected, is one of Naïa’s best features. Located a short golf cart drive away from the lobby, Naïa’s spa feels like a secluded oasis. Lillypads sit calmly on the surface of still ponds, and treatment rooms—all housed in small, individual wooden buildings—overlook the vegetation. The masseuses will alleviate you of all pent up stress with expert hands and sweet-smelling lotions exclusive to the resort.

The town of Placencia is only a short drive away, and the Naïa can shuttle you wherever you need to go. Eat and drink at Barefoot Bar or Tipsy Tuna, walk along the paths near the beach to find handmade treasures to take home, and hang out by the docks and watch the fishing boats come and go. Then go back to your little slice of paradise on the Caribbean shores.

Jamaica’s primary public art museum, the largest of its kind in the Caribbean, is a key part of the island’s history. Established in 1979, it houses more than 2,000 pieces ranging from pre-Columbian works to those of contemporary Jamaican artists and also mounts temporary exhibitions on various aspects of Jamaica’s history and culture. The collection continues to expand and now includes videos, graphic designs, and street art. Guided tours are available, and there’s an on-site coffee shop and gift store.

An archipelago within an archipelago is already an astonishing fact to grasp, but Îles des Saintes, made up of nine islets, only two of them inhabited, is full of yet more surprises. Hop on a daily ferry ride south from Trois-Rivieres in Basse-Terre to these gorgeous offshore islands around a stunning aquamarine bay dotted with sailboats and hugged by coral reefs. Also known as Les Saintes, these islands combine a traditional Caribbean setting of secluded beaches, forts, and towering palm trees with a chic French village lifestyle. The streets here are free of cars, the winding roads to be explored by electric scooter or on foot. Hike to Fort Napoleon for a breathtaking panoramic view over Les Saintes Bay, explore the surrounding waters by catamaran, go diving off the bluffs, sample some of Guadeloupe’s best French and Creole fusion restaurants, and shop the boutiques for French fashions and local jewelry.

Surrounded by swaying palms, tropical flowers, pink sand, and sapphire waters, the 100-acre Fairmont Southampton is Bermuda’s ultimate luxury destination. The 593 rooms and suites are among the largest on the island, and feature marble baths stocked with Le Labo products and private balconies that look out onto the Atlantic Ocean, Great Sound Harbour, or the lush landscaping of the on-site Turtle Hill Golf Club. A pool, beach club, dive center, kid’s camp, and tennis courts—plus that 18-hole championship course—offer plenty to keep guests busy. If you prefer to kick back, opt for a lavender-oil massage at Willow Stream Spa, a sprawling space complete with a well-stocked health club, sauna, and steam rooms, or grab a sundowner at one of the resort’s 10 restaurants, bars, and lounges.

Despite its size (10 square miles) and population (fewer than 170 permanent residents), Little Cayman enjoys a worldwide reputation among serious divers. The island is renowned for its exceptional underwater visibility and vertigo-inducing walls, especially north-shore Bloody Bay. Dive boats flock to Three Fathom Wall, where bulbous coral heads teeming with fish rise to within 10 feet of the surface. Snorkelers are likely to encounter schools of blue tang and stoplight parrot fish, as well as hawksbill turtles and nurse sharks.

A tour of St. Nicholas Abbey is a chance to explore one of the finest so-called great houses of Barbados. Not an actual abbey, the well-preserved Jacobean plantation mansion in the northern parish of St. Peter dates from the mid-17th century and is filled with antiques. On the mahogany tree–dotted manicured grounds, visitors can also see the old steam mill and rum distillery that are still in operation; the output from the latter, and other local products, are sold in the gift shop.

A visit to Sulphur Springs, which is dubbed the world’s only drive-in volcano, is one of the most unusual excursions you can make in the Caribbean. You’ll smell the rotten-egg stench of sulfur and see steam rising around the dormant volcano’s crater upon arrival. (Don’t worry: The last time the volcano erupted was two centuries ago.) Locals claim that soaking in the mud baths then rinsing off with a dip in the hot springs will rejuvenate your skin and relieve mosquito bites and minor skin problems. Be sure to take a before-and-after selfie to determine whether you look younger after the experience.

The interior of the Catholic Church of the Assumption, in the heart of Soufrière town, will surprise with its decidedly Caribbean hues and French design: an ornate wood ceiling vaulted to resemble the ribs of a boat, baby blue pillars, and brightly colored stained-glass windows. Visitors are welcome to join in the Saturday evening mass at 6:30 or Sunday morning mass at 8:30, both with the sermon in English and Creole. A quick and respectful tour is also possible at other times to admire the architecture, including the partially blue-painted exterior. While there is no printed information on the church inside, it’s worth a stop.

The most important historical site on Guadeloupe’s miniature archipelago of Les Saintes also boasts one of the most breathtaking views in the Caribbean. Perched some 400 feet above Les Saintes Bay, Fort Napoleon’s panoramic view of the water—dotted with sailboats and surrounded by bluffs—is worth a visit to Terre-de-Haut on its own. But it’s of historic interest as well. Rebuilt in the mid-19th century after the British destroyed it, the fort turned into a prison that was used during World War II. It was restored in the 1980s and houses a museum showcasing the history of Les Saintes. You can stroll inside to see the former grounds that served as a jail, and walk the botanical gardens afterwards, filled with the island’s various cactus species. Look out for iguanas peeking out of holes in the fort’s walls, as ubiquitous on the grounds as they are all over the island. Take in the glorious scenery for as long as you like before descending back down, on foot or on your rented electric scooter.

When it comes to beach bars, it doesn’t get much better than this open-air spot on picturesque Cockleshell Bay. During the day, guests can take advantage of lounge chairs, beach volleyball nets, and snorkeling gear rentals. Friday nights bring bonfire dinners, while Sunday afternoons feature live bands and dancing. The menu is heavy on seafood prepared in the traditional Caribbean way, with popular dishes ranging from corn chowder to coconut shrimp and conch fritters.

With its world-renowned chef and ultrachic decor, Blue—tucked discreetly into the Ritz-Carlton Grand Cayman—seems the sort of place you’d find in New York or Paris. But the main draw is decidedly local: spectacularly fresh ingredients sourced largely from the sea right outside and served up in such specialties as lightly seared wahoo with bok choy and kimchi broth; or poached halibut with sunchokes, salsify, and truffle jus; or bread-crusted red snapper with squid and sofrito sauce. If you’re feeling ambitious, go for the gusto with a six- or seven-course tasting menu—and tack on the wine pairings.

This property is currently closed for hurricane-related repairs.

Peter Island is “an oasis of tranquility,” known as much for its five flawless beaches as its word-class spas and luxurious ocean view villas. The island is the largest of the private islands and the fifth largest of the 60 islands in the BVI. Visitors can hop a ferry to reach the island from Tortola or opt for booking a helicopter, water taxi, or private yacht.