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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.

Among the three Cayman Islands, Brac is the most topographically endowed, thanks to its distinguishing feature: the Bluff, a limestone cliff rising along the length of the island and topping out at about 140 feet at the eastern end. Between that and the island’s densely forested interior, the local hiking options have a lot to offer—one of the best cases in point being the Lighthouse Footpath, a trail that runs two and a half miles (one way) along the bluff’s edge and that serves up endless sea views and likely encounters with the absurdly adorable brown boobies and soaring frigate birds. Try to go in the morning or late afternoon, and of course, take along plenty of water: You’re looking at a two-hour outing to the most beautiful of boonies.

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.

As of May 2018, El Conquistador Resort and Las Casitas Village are closed indefinitely, due to damage sustained during Hurricane Maria.

Situated atop a 300-foot bluff on the eastern tip of Puerto Rico, El Conquistador Resort, a Waldorf Astoria Resort, spreads across 500 acres overlooking the converging waters of the Caribbean Sea and the Atlantic Ocean. A stay at El Conquistador is a transformative experience. Guests can relax at the Eucalyptus steam room, enjoy exotic cocktails while gazing at the El Yunque Rainforest, or even kayak around a private island. Guestrooms and suites are divided into five villages, and feature ocean views, 23 restaurants, an 18-hole golf course, a state-of-the-art aquatic playground/water park for families, and the resort’s private island, Palmino Island, featuring water sports and white sand beaches.

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.

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.

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.

Checking out the famously preserved mummies at the world’s oldest public museum is on many London wish lists, but there’s much more to the British Museum than ancient Egypt. Other must-sees include the Elgin Marbles and the African masks, both part of an enormous collection that spans ancient Iran to modern Sweden. The Great Court, which was cleverly revamped with a geometric glass roof by Foster + Partners in 2000, is a spacious gathering area with a shop and a café—and a sight worth seeing in itself.

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.

On Tahiti’s rocky east coast, the volcanic Lava Tubes of Hitiaa are underground channels and eroded sections of rock in caves that have been penetrated by water. Although you can visit solo, it is really best to visit with a guided 4WD tour. Check with Marama Tours, which also does a range of other island tours from encounters with dolphins to 4WD trips across the Papenoo valley that is rich in waterfalls and archeological sites.

Battery Point was one of the first lighthouses on the California coast, and today its unique island spot makes for a historical visit that doesn’t have to be boring. The Del Norte County Historical Society operates the lighthouse and its accompanying museum—open daily during the summer, but strictly on weekends from October to March. Notably, the lighthouse is accessible to the public only during low tide. Guests have to make their way across the land bridge, which can quickly go underwater when the tide comes in. Once on the small rocky island you can check out the lighthouse keeper’s home, which has been memorialized as a museum with vintage odds and ends from the days when the lighthouse was operational. Many people also come out simply to admire the natural beauty.