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One look at this hilltop fort, perched over the Port of Kingstown, and you know the British built it to fight the locals rather than to meet any threats coming by sea—all the cannons face the island’s rugged interior, where the Caribs lived. Inside the fort, you’ll find a series of murals depicting the bloody Carib wars. Kids will love exploring the old buildings, and everyone will enjoy the views.

Between 1812 and 1815, the British ordered the construction of 300-foot-long Jasper Rock Tunnel (more commonly known as Black Point Tunnel) to provide better access from the cane field to the sugar factory to the ships for export. Slaves were responsible for the actual building, manually cutting through the mountain with shovels, picks, and sledgehammers. Now part of the Black Point Historic and Recreation Park, the tunnel also served as the site for several scenes in the first Pirates of the Caribbean movie.

The waters surrounding Bequia beckon scuba divers with everything from brilliant sponges, colorful fish, and deep-water corals to shallow reefs, sheer walls, caverns, holes, and wrecks. While the area is home to 30 or so easily accessible diving sites, you should head to the designated marine park, which occupies seven miles along Bequia’s leeward coast. Family-run outfitter Dive Bequia (located on Belmont Walkway in Port Elizabeth) offers three dive trips to the park each day, along with instruction, certification, and rental gear. Divers must be at least 8 years old, but snorkelers of all ages are welcome as well.

Locals consider La Soufrière—St. Vincent’s massive active volcano that last erupted in 1979—the “queen of climbs.” Approachable from either the leeward or windward coast, the hike to the 4,000-foot summit is a serious, all-day excursion. You’ll need stamina and sturdy shoes—and a knowledgeable guide from the National Parks Authority—to safely reach the top, but once there you’ll enjoy breathtaking views of the surrounding landscape and sea. Keep your eyes peeled for a rare sighting of the St. Vincent parrot on the way back down.

If you were to picture the perfect Caribbean beach, it would probably look something like Salt Whistle Bay on Mayreau. Here, clear, turquoise waters lap at 2.5 miles of sparkling white sand, while palm trees, seagrape plants, and flowering bushes provide shady spots for lounging. At one end, you can walk the few yards of land that separate the Caribbean and Atlantic sides of the island. The only catch is that you’ll need a boat to reach the beach, so rent your own or book a day sail to Mayreau.

Among several sea and land excursions, locally owned Fantasea Tours offers full-day whale- and dolphin-watching trips along St. Vincent’s leeward coast. You can expect to see pilot whales, orcas, and several species of dolphins year-round, but the best time to spot them is December through April. Huge sperm whales and humpbacks stop by seasonally, usually from October through January. Regardless of when you go, you can look forward to an exciting, comfortable tour. Fantasea’s staff is extremely knowledgeable, and its boats and equipment meet the highest safety standards.

For an introduction to the Rastafarian culture and lifestyle, head to OJ’s Ital Cart in Basseterre. The brightly painted food truck takes a pure approach to its menu, offering vegetarian fare that’s fresh, natural, and from the earth. Ingredients are grown without chemical pesticides or fertilizers, and even the salt used to flavor dishes is iodine-free. While lines often wrap around the block at lunchtime, the vibe is always fast and fun. When you’re seeking something healthy, join the crowds for pastas, sautéed soya, fresh local juices, and more.

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.

Dating to 1521, the Cathedral of San Juan Bautista isn’t just one of the oldest buildings in San Juan—it’s the second-oldest cathedral in all of the Americas. Go inside to see the tomb of Spanish explorer Ponce de León, who founded the first settlement on Puerto Rico and in 1509 was named the island’s first governor. The remains of St. Pio, a Roman martyr, can also be seen in the cathedral—the saint’s mummy has been displayed here in a glass box since 1862.

Scattered with Victorian mansions, St. Paul’s tree-lined Summit Ave. is one of the most beautiful residential streets in the Midwest, with famous former residents including author F. Scott Fitzgerald and early railroad entrepreneur James J. Hill. Guided tours are offered from the James J. Hill House Wed–Sun, but it is also a worthwhile independent stroll. Make sure to start or end at the gorgeous St. Paul Cathedral, overlooking downtown St. Paul.

No visit to Antigua is complete without taking in the sunset atop Shirley Heights Lookout at its weekly Sunday sundowner party. The view from Shirley Heights is without a doubt the most famous, most photographed, most celebrated vista gracing Antigua. Immediately below, English and Falmouth Harbours clutch their bays. On clear days you can see Guadeloupe to the south and Montserrat with it’s still active volcano to the south west. It does get busy, so expect a crowd and while there might be a couple locals sprinkled in here and there, it’s mostly visitors. Around 7ish, the tunes crank up with either some reggae classics, some pumping soca, or even live a steelpan band. Smoke from a collection of barbecues compete with the music to fill the air and stimulate your senses. Expect chicken and ribs slathered in local flavors, plus burgers for the less adventurous. I did have some trouble getting grilled fish on my last visit, but once I found some, it was charred to perfection.

When you’ve had enough of the hectic hustle of tourists and traffic in Times Square, seek refuge at Haven, a rooftop lounge located on the top of the Sanctuary Hotel on 47th Street between 6th and 7th Avenues. The owners of this chic establishment spent a considerable amount of time in Saint-Tropez and have made an effort to make their guests feel like they have been transported there. Chill at the bar, relax under oversize umbrellas at one of their cedar tables, or go all out in an open air cabana, swathed in sheer white drapes while re-fueling with foods from their French inspired menu. You can even get your anti-oxidants while you drink by ordering a Night Sky- one of their signature cocktails made with acai blueberry vodka and fresh lemonade, garnished with a skewer of blueberries. The manager Katerina was wonderful, making sure we had everything we needed and even shaking cocktails herself to help out the busy bartenders. If you’re looking for some excitement after your rooftop recharge, Haven hosts a rotation of DJs, features events such as burlesque shows, and has a VIP area overlooking the main roof that is available to rent out. With plans to install heating and encase the rooftop, Haven will soon be able to provide the refuge you need before a show, after work, or after hours all year long.

Named for its owner’s “poz-itive” vibe, this casual, welcoming restaurant ranks among Dominica’s best. Expect Cajun, Creole, and Caribbean fare in the mix, along with fusion dishes and strong vegetarian options. Menu standouts include callaloo soup, veggie rice, and snapper in coconut-curry sauce, but the lobster, grilled with lemon-garlic butter, tends to steal all the headlines—or at least those not occupied by the fresh juices and home-infused vodkas. Open for dinner only, Poz is quite small in size, so make a reservation to avoid waiting for a table.

Even though it’s just 200 yards off the coast of St. Vincent and accessible via a two-minute ferry ride, Young Island feels worlds away from the cares of mainland life. The resort’s 29 guest cottages, which are outfitted with tropical-chic wicker furnishings, stone walls, and louvered windows, provide a plush landing spot after days spent diving among sea turtles and sea horses, hiking neighboring trails to spot the ruins of Fort Duvernette, and swimming up to the Coconut Bar, located on a floating platform 30 feet offshore. Each week, the on-site restaurant serves up Caribbean barbecue favorites like pigeon-pea-and-pumpkin stew, corn fritters, and molasses-glazed wings, making for a delicious stay.

Deep in the wilderness about an hour’s drive north of Kingstown, Dark View Falls cascade off a cliff and into a pair of natural pools, where everyone gathers to swim in the crisp, clear water. The hike to the falls takes only about 10 to 15 minutes, but involves crossing a jungle-style bamboo bridge across the Richmond River. After passing through a clearing in a picturesque bamboo grove, you’ll arrive at the first fall, where you’ll find a gazebo, changing room, picnic area, and viewing platform for enjoying the beautiful scenery. Another short, more difficult walk will take you up to the second fall, directly above the first.