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Take a hike into the cool confines of an underground cave system on Middle Caicos Island. Conch Bar Caves is the largest nonsubmerged system in the region, featuring a type of cave that is created by the karst process in which rain water slowly erodes subterranean channels through limestone. Exploring the interior will reveal chambers with tidal pools, rock formations, and four species of bats. Some instances of graffiti within the caves are over a century old, left by guano miners during the late 1800s and early 1900s. Visitors must hire a local guide to enter the caves.

Pass over limestone rocks and through a protected landscape and you’ll arrive at this enchanting pool, which gets up to eight feet deep at times. Surrounded by volcanic outcroppings, it’s so removed from other island attractions that it feels undiscovered and romantic. The water is warm and bubbly and there are some ledges for sitting, all of which make you feel as if you’re in a natural Jacuzzi. Whether you arrive by foot, mountain bike, or jeep, the journey is as exciting as the destination itself. For a dose of adventure, opt for the half-hour guided horseback tour, which winds past caverns and other rock formations on its way to the pool.

This comprehensive museum, which was dedicated in 2002, is housed in St. Kitts’ historic treasury building. Constructed from hand-cut limestone in 1894, the building is still known as the gateway to Basseterre, thanks to its imposing size. Inside, three galleries trace the history of St. Kitts from the island’s indigenous inhabitants to its independence in 1983. Visitors can learn about the sugar, slave, and rum trades as well as carnival customs, and see traditional dress on display.

You’ll have to pick your jaw up off the ground before you start your alfresco breakfast or dinner on Elk Island, in the middle of Jackson Lake in Grand Teton National Park. Just one mile from Elk Island (the largest island in Wyoming—not a hotly contested title), the hulking Mount Moran explodes up 7,000 feet from the lakeshore. It’s so close you might be able to spot crevasses on one of its glaciers. In this setting, standard fare—trout, steak, and chicken at dinner, and eggs, pancakes, and hash browns at breakfast—tastes almost sublime. The cruise to and from the island is a bonus.

Privately owned Cavallo, just a mile off Corsica, is the only inhabited part of the Lavezzi Islands. It’s no more than half a square mile in size (120 hectares), but it was valued even back in the days of ancient Rome, when the Romans established granite quarries here. And while the island is French, it has been a favored retreat for Italian vacationers since the 1970s, when celebrities first came to frolic among its secluded coves. It’s still a peaceful oasis, with only bicycles and electric golf carts allowed on its winding roads.

The past two decades have seen the dozens of islands scattered across Boston Harbor transformed from barely noticed dots on the horizon to one of the city’s most popular attractions. The Boston Harbor Island National Recreation Area, established in 1996, has propelled them into prominence, with ferries carrying day-trippers and overnight campers from downtown Boston, Hingham, and Hull to eight of the islands (19 more are accessible by private boat or charter excursions). Most visitors head to Georges Island, home of the Civil War–era Fort Warren, or the beaches and hiking trails of Spectacle Island, the one closest to downtown Boston. (Don’t skip the concession stands here: The food is from James Beard Award–winning Boston chef Barbara Lynch.) You can also camp on Peddocks, Grape, and Bumpkin islands, or take a tour to Little Brewster Island to witness the 300-year-old Boston Light, the nation’s oldest lighthouse.

If you want to eat like a local, try heading to Potter’s Cay—an enclave of modest fish shacks tucked beneath the bridge to Paradise Island. The most famous of these is Twin Brothers, which serves up paper plates full of deliciously authentic cracked conch, conch fritters and citrus-marinated conch salad.

Retail therapy takes on new significance at this nonprofit, where the vintage-inspired dresses, jackets, and bags are designed and handmade by the inmates of the women’s prison on Giudecca island as part of a skills training program. Fortuny and Bevilacqua donate some of the more sumptuous fabrics, and colors tend to be bold and cheery.

In the southwest of Providenciales, this national park encompasses the tranquil Chalk Sound lagoon, a large expanse of shallow water connected to the ocean by a small channel. Check out the fringe of jagged limestone, called ironshore, along the shorelines of the lagoon and its small islets. You can rent a car and explore scenic Chalk Sound Drive, or you can stop at Las Brisas Restaurant to rent kayaks for a paddling adventure. See if you can spot stingrays and small sharks finning through the water, or the local rock iguanas foraging on the islands.

Hogfish Bar and Grill, under a thatched palapa roof with open sides, is tucked in among the boats and gulls of Safe Harbour Marina in Stock Island. In short, a meal or a drink there makes you feel like an insider, a salty local far from the crowds downtown. That in-crowd feeling is burnished on weekends, when local bands play sets, or during one of the events held by Hogfish during the season, like shrimp boils. The simple food is served generously on plates crowded with side dishes. The hogfish sandwich, served fried on Cuban bread, is the stuff of late-night-post-beer legend.

Store Bay, just outside Scarborough, is one of Tobago’s most popular beaches. Reserve some time after your swim for a visit to the dozens of bright and cheery craft shops and food stalls that make up the Store Bay Beach Facility. Need souvenirs? Browse for island crafts like batik, sandals, jewelry and items carved from wood and coconut shells.

One of the few hotels on picture-perfect Grace Bay Beach that can work for both honeymooners and families, Seven Stars sits on 22 acres of lush grounds at the edge of Princess Alexandria National Park and has studio to four-bedroom plantation style suites available. All feel very private. Besides wraparound terraces with awesome ocean views, the rooms here all feature full kitchens, making it easy to cook your own lunch or make snacks for the kids. That said, the house restaurant, aptly named Seven, is very good, so plan on dining here at least a few times. The spa is also excellent - perfect for honeymooners - and there is a dedicated activities concierge that will arrange all sorts of water sports and even a kids’ camp.

This 1763 plantation house has an interesting tale to tell. It never employed slave labor, and its owners—descendants of Carib Indians—are commemorated with statues and figures spread throughout the rooms and gardens. Visitors can take tours of the house, gardens, and old overseer’s house, then enjoy beautiful views of the neighboring island of Nevis.

Jambe de Bois is an unpretentious food escape set idyllically in Pigeon Island National Park. The café—made of stone, driftwood, and thatch—serves up a beach view, an island atmosphere, and a simple menu that will keep you happy for hours. Sit on the deck at one of the picnic tables, and snack on sandwiches, salads, or local dishes like rotis, curries, or fish fillet with rice and peas at lunch and dinner. Come for happy hour or join the locals for live jazz on weekend evenings. The local art on display inside is for sale.

Yo, ho, ho and oh, my! Up on Government Hill, this watchtower, built circa 1678, is known as Blackbeard’s Castle and is literally the stuff of legends. Although it’s open for debate whether the notorious pirate ever used the five-story tower as a lookout, one thing is for certain: Its views are tops. Nearby the flower-lined 99 Steps (technically there are 103), built in the 18th century of ship-ballast brick, lead from historic Kongens Quarter to some more terrific views of the island.