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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.

Le Viaduc des Arts, an abandoned railway line, was converted into an elevated park, and the arches below it were turned into ateliers for artisans. Parasolerie Heurtault is one of the workshops worth a detour. Master artisan Michel Heurtault created corsetry in haute couture houses before pursuing his childhood passion of making and restoring bespoke umbrellas. In the showroom, ready-made umbrellas and precious handles fill shallow drawers. Rolls of silk and natural fiber fabrics are gathered into colorful bouquets in the workshop beyond. In addition to providing shelter from the rain, Monsieur Heurtault will repair family heirlooms and makes spectacular pieces for period films.

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 Caramoan area, on the eastern tip of the Caramoan Peninsula in Bicol, is a rugged and remote landscape of white-sand beaches, rich woods, swampland, lakes, and caves. Numerous seasons of the reality TV show Survivor have filmed around this region, including at Gota Beach. Most travelers explore the pristine Caramoan Islands by small outrigger boat. There are too many to scope out in one trip, but don’t miss famous Matukad Island with its pure white sands, exotic rain forest, limestone rock formations, and even a hidden lagoon. Another must-visit is Manlawe Island, a one-kilometer-wide sandbar surrounded by ankle-deep water. Other highlights include Cotivas Island, Gota Island, and Sabitang-Laya, a triangular landmass with powdery sand, caves, and superb snorkeling. Accommodations in Caramoan include family-run inns that are equipped with modern amenities but rustic enough to accentuate the region’s remote and unspoiled ambience.

I’m not one to skip breakfast, especially in Italy, where thoughts of cappuccino, pastries, and local ham tend to rouse me early from slumber. But on my first morning at the Hotel Sant’Angelo, in the old quarter of Matera, I was having a hard time dragging myself from the creature comforts of my cave. Staying in a cave, it turns out, can be surprisingly pleasant. There was just one small window high overhead, but the room and adjoining bath were in no way dank—a testament to the natural ventilation that keeps the caves cool and comfortable. The wavy contours of the white tufa-rock walls conjured a feeling of being enveloped in some primordial womb. Yet there were modern amenities: luxurious linens, Internet service, a telephone. Fred Flintstone never had it this good. I might have snoozed until noon, were it not for an impatient mate eager to see the sights. We had arrived in the village the previous night after a long drive across the treeless plains of the Basilicata region, located at the instep of Italy’s boot. Matera is an enchanted world of Stone Age splendor. Known as the sassi (Italian for stones), the bisque-colored hilltop cave homes comprise one of the oldest continuously inhabited places on earth, according to UNESCO. The caves have provided shelter for more than 7,000 years. A millennium ago, shepherds inhabited them and carved churches into the rock; during the Renaissance, the area prospered and elaborate buildings were carved out, the excess tufa sculpted into ornate facades. By the early 1900s, the sassi had fallen into neglect. Families and their animals crowded into the caves for warmth, and disease was rampant. When writer Carlo Levi brought this tragic state of affairs to light with his 1945 book Christ Stopped At Eboli, the Italian authorities moved residents en masse to modern housing—leaving the sassi abandoned, save for the occasional crew brought by film makers (Pier Paolo Pasolini and Mel Gibson among them) in search of a biblical-looking backdrop. It was only in the 1990s that the Italian government encouraged people to move back. Residents revamped the cave dwellings as homes, restaurants, and inns. When the Sant’Angelo opened in 2004, it was the area’s first luxury hotel. The 19 cave rooms are sparsely but tastefully appointed with rustic wooden furniture. Some carved decorations—crosses, hearts, an owl—date back hundreds of years. Fossilized shells embedded in the walls reveal that the region once lay underwater. Eventually, my fiancé and I did emerge from our cave to wander the town’s ancient alleys. A local guide named Dora Cappiello took us into some of the 150 chiese rupestri (rock churches), where she pointed out wine troughs and frescoes of San Nicola, the patron saint of local shepherds. We also visited a cave dwelling that had been restored to resemble its state when the caves were equal parts manger and living space.
Simple, delicious meals punctuated our explorations. The curvy walls of Baccanti, a cave restaurant, created a private nook where we feasted on silky pappardelle pasta with a cinghiale (wild boar) ragu, accompanied by a dry, fruity red aglianico from the nearby Vulture wine region. Tired and sated after a full day, we headed back to our cave—on moonless nights, a flashlight or trail of bread crumbs is advised for the stumble back to the hotel—where the promise of a deep, sound night’s sleep awaited. —Amy Cortese Hotel Sant’Angelo, 39/0835-314010, from $211 for a double. This appeared in the March/April 2010 issue.

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.

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.

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.

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.

On the west side of Arenal Volcano, this 900-acre tropical reserve was a labor of love for owner and architect Jaime Mikowski, who spent years planting acres of native plants and coaxing the land’s natural mineral springs into a river that now flows throughout the property, spilling over into dozens of waterfalls and pools that range from 72 to 105 degrees. Spacious rooms have marble floors and streamlined furnishings; splurge on a suite, which features a private terrace and a Jacuzzi tub—a little superfluous considering all the other options for soaking in warm water here, but who’s complaining? There are also five swimming pools, one with a swim-up bar and waterslide, and a spa comprising 12 bungalows with treatments that all include, you guessed it, a dip in a thermal spring-fed tub. While the property is also open to day trippers, guests of the resort have exclusive access to Shangri-La Gardens, an adults-only lounge area with pools, cabanas, and a folliage-filled bar.

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.