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Standing at 3,793 feet, this towering, verdant peak is the island’s highest point. The dormant volcano is covered mostly in rain forest and capped with a cloud forest, making it ideal for a beautiful hike. The climb is an arduous one, however, and shouldn’t be attempted without a guide. If you manage to reach the top, you’ll be rewarded with sweeping views of St. Kitts, the Caribbean Sea, and neighboring islands like Nevis, Antigua, and Saba.

Baseball had nothing to do with the naming of Fenway Park: The stadium gets its moniker from the nearby Back Bay Fens, a stretch of saltwater marsh in the heart of Boston that was landscaped into a park by Frederick Law Olmsted. The Fens are among the wilder parts of the Emerald Necklace, 1,100 acres of parklands running from the Charles River to Brookline that include familiar spaces like the Boston Common and Boston Public Garden but also less-traveled (by visitors, anyway) sections like Olmsted Park, Jamaica Pond, the Arnold Arboretum, and Franklin Park. The arboretum, part of Harvard University and established in 1872, is one of Olmsted’s most unaltered terrains, with paths running up and around 261 acres of woodland interspersed with a curated collection of trees, plants, shrubs, and vines native to New England.

After opening in 2014, it didn’t take SALT Plage long to start appearing on lists of the world’s best beachfront restaurants. At the Christophe Harbour dining destination, guests gather on a palm-shaded deck overlooking White House Bay for craft cocktails and Caribbean fare, served from a corrugated steel bar that manages, like the menu, to project both a casual and sophisticated vibe. Live music and full-moon parties make this the place to be for sunset and beyond.

Despite the industrialized patty chain stores across Jamaica, the love for handmade patties continues in some parts of the island. Miss Sonia’s entrée-size, crusty patties are served at a small roadside restaurant across from the beach in Negril. She offers traditional fillings like beef or callaloo, as well as others like lobster and conch that she introduced at the suggestion of her numerous return visitors to Jamaica. When you get your order, be sure to shake on some of the secret spicy sauce—Miss Sonia won’t tell you what’s in it—and then dig in.

One of the perks of staying at the St. Kitts Marriott Resort is the opportunity to test your skills at the Royal St. Kitts Golf Club, an 18-hole, par 71 course laid out along the island’s Caribbean coast. If you’re not a Marriott guest, however, head to the Irie Fields Golf Course at Kittitian Hill, where organic farms fringe the fairways. Designed by World Golf Hall of Famer Ian Woosnam, the course is maintained without pesticides or chemicals—if you see a herd of sheep grazing on the back nine, let them play through.

Shipwreck is a classic Caribbean beach bar with umbrellas (in both the sand and the drinks), snorkeling off the shore, and live music on Sundays from “4ish to 6ish.” Don’t miss the fish tacos, claimed to be the best you’ll ever taste. And bring your phone—the photo to get is one of the local monkeys that frequent the beach.

Talk about a beach day. This feet-in-the-sand eatery serving burgers, chicken wings, and fries is more than a laid-back fish shack. Sure, there are all the requisite beach-bar amenities—a cool cocktail list, live music, and a line of loungers facing the water. But additional perks include free Wi-Fi, showers, and lockers; what’s more, concession stands are on hand to rent out water-sports gear. The bay itself is breathtaking with limestone rocks creating a barrier protecting it from the open ocean, meaning the shallow turquoise waters are perfect for paddleboarding. Tobacco Bay is also one of the best snorkeling spots in Bermuda.

Barbados is considered the most British of the West Indies, and its historic churches, which wouldn’t be out of place in an English village, help it claim that title. On the site of older churches that were destroyed by fire and hurricanes, some dating as far back as the 17th century, St. John’s Parish Church is an early-1800s dark stone Gothic gem. Though the earliest St. John’s church was constructed in 1645, the one that stands today is largely from 1836, replacing a building destroyed by a hurricane in 1831. Its remarkable pulpit is made of ebony, mahogany, locust and other local woods. Many prominent figures are buried in the graveyard, which has views of the coast.

Along with pink sands and green golf courses, these subterranean grottoes are among Bermuda‘s iconic sites. First discovered in 1907 by the same family who still owns them, the caverns have spectacular crystal formations, crystalline pools, and underground waterways. Guided tours of the Crystal Cave, which measures more than 1,600 feet long and more than 200 feet deep, explain the differences between stalagmites and stalactites as well as the science behind the impressive underwater formations. A visit to the adjacent Fantasy Cave, which is deeper still, is included in the ticket price.

If you’re driving out to the beaches or bars of St. Kitts’ southeast peninsula, make sure to stop for an envy-inducing photo op at the top of Timothy Hill. Up here, your 360-degree view includes the Atlantic Ocean, the Caribbean Sea, Friar’s and Frigate bays, Nevis, and the hilly peninsula itself.

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.

St. Kitts’ water taxis—basically anyone with a boat willing to make the crossing to Nevis—will drop you right on this beautiful stretch of sand, making Oualie Beach the perfect day trip. Once on land, head to the Oualie Beach Resort, where you can hang with guests and locals at the on-site restaurant and bar. If you’re feeling adventurous, ask the bartender for a sample of one of the house-infused rums, made with a variety of local plants and herbs. Afterward, walk down to the beach, where you’ll find watersport vendors and even a small spa for some additional relaxation.

Golf enthusiasts will find plenty to love at Pompano Beach Club—the family-owned resort is practically next door to the world-famous links of Port Royal. But the former fishing club is also a haven for anglers of every stripe: You can grab a complimentary rod from the hotel staff and wade out nearly 400 yards on the nearby sandbar to cast for bonefish and—what else?—pompano, or charter a vessel to catch yellowfin tuna and mahi-mahi on a deep-sea voyage. Back on land, the 75 guest rooms provide laid-back ambience thanks to floor-to-ceiling windows perfect for enjoying panoramic ocean views. Better still, retire, rum swizzle in hand, to the terrace of the appropriately named Sunset Lounge to take in the postcard-worthy vistas.

Near the northern end of Andros Island, about 15 minutes by air from Nassau, remote Kamalame Cay is worth the effort it takes to get there. The 96-acre private island features 34 rustic-chic rooms and suites, all within steps of a white-sand beach, as well as a central Great House where guests come together to sip wine before dinner and share stories afterward (of course, many opt for a secluded, candlelit meal set up somewhere along the three miles of shoreline). A range of seaside activities keep everyone from the kids to newlyweds to the occasional celebrity happy. There’s a freshwater swimming pool, an over-water spa, world-class fishing off the coast, and entertainment by local “rake-and-scrape” bands. And for those who live in fear of being unplugged, relax. Kamalame Cay offers hotspots around the island for full cell service (if you want it) and Wi-Fi in the reception area.

Enormously popular, the Cliff Restaurant indeed sits right over the sea in Saint James Parish, and all of the tables on its two levels afford fine views. Many of the seafood dishes, such as curry mussels and chargrilled swordfish, are Asian influenced. At night, the outdoor seating area is illuminated by torchlight, revealing the stingrays swimming below.