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Crashing waves serve as the soundtrack to your stay at Elbow Beach, situated on 50 lush acres along Bermuda’s rose-hued southern coast. Decorated with exposed beams, tiled floors, and neutral color schemes, the spacious cottage-style rooms are the portrait of coastal elegance—think coral-emblazoned throw pillows, wicker benches at the foot of the beds, and ocean or garden views through French doors. Polished-pebble paths lead the way to the spa, which offers treatments inspired by local ingredients, from a ginger-and-coconut scrub to a hibiscus bath. Grab a rum swizzle in the lounge, relax by the curving perimeter of the pool, or snorkel, swim, and kayak at the hotel’s private beach. You might also prefer to hit the pavement: Elbow Beach is mere minutes from the capital of Hamilton, Gibb’s Hill Lighthouse, and four 18-hole championship golf courses.

Located in East End Village and painted in Anguillan flag colors, the Heritage Collection is Anguilla’s only museum. It showcases the island’s history and geology from the time of the Arawaks to the 1969 Anguillan revolution, with additional displays on the British invasion (derisively called the “Bay of Piglets” by the press) as well as on Queen Elizabeth II’s royal visit. Established in 1996, its collection includes photographs and artifacts from the island’s major eras, including the days of slavery and the phosphate trade. If you’re lucky you’ll meet Colville Petty, the museum curator and founder, and garner some of his unique insight on Anguillan history.

Why we love it: A 900-year-old fortress-cum-prison reimagined as a luxurious getaway

The Highlights:
- Historical details like artifacts, original ironwork, and a stone arch bearing the seal of Abdul Hamid II
- A fourth-floor infinity pool with uninterrupted views of the Mediterranean Sea
- A full-service spa with a Turkish hammam

The Review:
Located right on the main square in the old city of Jaffa, The Setai Tel Aviv is steeped in history. Built by the Crusaders as a fortress in the 12th century, the property later served as a kishle (jailhouse) under the Ottoman Empire, then a British command post during Israel’s War of Independence. When it became a hotel, the original building, with its stone corridors and inner courtyards, underwent a meticulous restoration that included archaeological digs to uncover several artifacts, which guests can now see in the lobby. Those eager to learn more about the hotel’s history can also walk through the large entry arch, crowned by the seal of Abdul Hamid II, or check out the stone-and-iron prison cells behind the grotto-like lobby bar.

Spread over three newly created floors, the 120 rooms and suites feature an Ottoman-inspired design, complete with richly colored Turkish rugs, laser-cut pendant lamps, dark wood furniture, and sleek, textured headboards. Spacious bathrooms further the luxurious vibe with granite sinks, large bathtubs, and separate rain showers. Elsewhere on property is Jaya, where guests can indulge in an ample breakfast buffet and new-Mediterranean kosher food for lunch and dinner; former prison yards that serve as the hotel’s stunning front and rear courtyards, with comfy seating among verdant lemon trees; and a basement spa, which boasts a traditional Turkish hammam. Still, the hotel’s principal amenity has to be the fabulous infinity pool with panoramic views of the Mediterranean and downtown Tel Aviv—sunsets here are nothing short of spectacular.

The founders of Soho House and the developers behind such buzzy hotels as New York City’s The NoMad teamed up to turn the historic Midland Bank building into—what else?—a one-stop lifestyle hub that’s drawing regulars of both the suit-and-tie and hipster variety. Part-hotel, part-member’s club, The Ned (named for the moniker of legendary, 19th-century architect Edwin Lutyens, who first envisioned the building) features eight dining options set around the former banking hall, from Italian, French, and Californian spots to a New-York-style deli, Pan-Asian favorite, and lounge for an overflowing, British-style Sunday feast, complete with a Bloody Mary bar and mimosa trolley. Hotel guests also have access to a downstairs bar, and a wellness level with a nail bar, gym, separate hair salon and barbershop, Cowshed Spa, traditional Moroccan hammam, and vitamin IV drips by The Elixir Clinic. The spa level also features an indoor pool, while the Ned’s Club Upstairs offers a rooftop pool and restaurant (with views out to St. Paul’s Cathedral) to Club members or those staying in higher-category rooms.

The entire property is done up in cool, vintage-inspired design, including the 250 guestrooms, which range in category from Crash Pad and Cosy to Heritage and six types of suites. All feature 1920s flair, such as mirrored cocktail cabinets, wingback chairs, and Jazz Age motifs, as well as marble-mosaic bathrooms stocked with rainfall showers and 10 full-size Cowshed products. Suites have bonus perks like dining areas, bathtubs, and upgraded views. Take all the pictures you want in your room, but Insta-addicts may want to leave their phones behind when in select public areas: there’s a photo ban in any place that’s part of the Club membership, including that stunning rooftop.

Routinely crowned the city’s top seafood restaurant, Blue Water Cafe is also among the continent’s best. After honing his skills at Michelin-starred restaurants in Europe, executive chef Frank Pabst opened this Yaletown classic to marry fine-dining techniques with local, sustainable ingredients. Eventually, the restaurant became a founding member of the Ocean Wise program, which helps consumers make ocean-friendly seafood choices. When visiting, you can belly up to the bar—which boasts more than 200 whiskeys and 1,000 wine labels—or reserve a table in the elegant brick-and-beamed dining room, housed in a heritage warehouse. Come summertime, however, you’ll want to head straight to the patio for sushi and premium sake. Fancy a splurge? Go for the seafood tower, which showcases the bounty of British Columbia.

A tour of St. Nicholas Abbey is a chance to explore one of the finest so-called great houses of Barbados. Not an actual abbey, the well-preserved Jacobean plantation mansion in the northern parish of St. Peter dates from the mid-17th century and is filled with antiques. On the mahogany tree–dotted manicured grounds, visitors can also see the old steam mill and rum distillery that are still in operation; the output from the latter, and other local products, are sold in the gift shop.

It’s no coincidence that walking around Liberty feels as if you’re exploring someone’s grand home; the department store’s founder, Arthur Lasenby Liberty, wanted to create that very feel, and so in 1875 settled on a Tudor-style building that featured a jumble of interconnecting rooms. A wooden staircase at one end connects the six floors, and a paper room sells stationery in the store’s iconic floral Liberty print, fashion and beauty halls, a cafe, and multiple branded treatment rooms. Still, it’s the florist’s shop outside that seems to provide the main draw; as any passing tourist will attest, its colourful array of blooms is highly Instagrammable.

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.

Boat-building as an industry has existed on Bequia as far back as the 1800s. At one point, the island was even known as the “boat-building capital of the West Indies,” having produced the largest wooden vessel in the region. While construction has slowed over time, it still occurs—albeit on a much smaller scale—at places like Sargeant Brothers Model Boat Shop, just up the road from the ferry landing in Port Elizabeth, where Benson Phillips and other craftsmen make and sell their models. Handcrafted using hand planes, chisels, and carving knives, their boats are incredibly detailed and realistic. Choose from whale boats, sailboats, power boats, and wooden schooners, or commission Phillips to build a custom model of your own yacht. The simplest models take about a week to make, but there are always a few boats available for immediate sale, ranging in price from around $250 all the way up to $7,000.

Nothing says Santorini like an aqua-blue infinity pool, and Katikies has three of them—all the better to take in westward-facing sunset views. Carved out of the cliff side 300 feet above the Aegean, the hotel’s public spaces are connected by a series of bridges and Escher-esque stairways as they descend from the town of Oia above it. Cube-shaped rooms and suites are minimalist but inviting, nearly every surface painted or clothed in calming white; all have verandas, while a few large suites have outdoor plunge pools or Jacuzzi tubs and alfresco seating areas. Upon check-in, guests are given cell phones to summon 24/7 service from anywhere on the property. They use them to order light snacks at the poolside bar and restaurant or make reservations for some of the best sushi on the island at the champagne bar, but the candlelit rooftop restaurant—serving Greek and Anatolian cuisine—is about as romantic as it gets.

Getting to Onar Andros requires a fair amount of determination. A ferry from Athens or Mykonos takes you to one of the northernmost Cycladic islands (there’s no airport nearby); once you arrive at the port in Gavrio, it’s a slow 25-mile drive to the hotel. Your reward, however, is a tiny slice of Eden, an enclave of 10 stone-and-timber cottages set amid a lush river valley that’s only a five-minute walk to Ahia Beach, arguably the most beautiful in all the Cyclades. Built and maintained by the owner, Mateo, the accommodations are deliberately spare yet modern and comfortable, each with a pergola-shaded veranda with loungers and a hammock. Meals are served at a communal table, and what Mateo doesn’t grow organically, he sources from local fisherman, farmers, and bakers. Guests can even accompany him to pick fruits and vegetables to be used in that night’s dinner. After all, this is a place to ditch your devices and surrender to your surroundings.

In 2012, one of the world’s richest men—Oracle founder Larry Ellison—bought 97 percent of the island of Lanai. The single sweeping deal (reputed to cost $300 million) included the exquisite Four Seasons Resort, overlooking a marine reserve. The resort’s dining experience par excellence is Nobu, where celebrity chef Nobuyuki Matsuhisa presides over the perfect marriage of Japanese dishes and Peruvian ingredients. Kick things off with crispy Brussels sprouts or scallops with jalapeño salsa, then move on to sushi, hand rolls, or Wagyu beef. Save room for the Bento Box dessert with green tea ice cream and chocolate flourless cake. Or go old-school, if it’s on the menu, and order the mochi pound cake backed by yuzu-cherry jelly and peanut butter ice cream.

The Wauwinet makes the most of its coastal setting between the Atlantic Ocean and Nantucket Bay. Next to the Coskata-Coatue Wildlife Refuge, the resort has 32 rooms, plus four cottages with separate living rooms and the three-bedroom Anchorage House across from the main inn. In addition to private beach access and bikes to explore the island, guests can take out a kayak, play a game of tennis, or watch a movie in their room with hot buttered popcorn. A spa offers sea-inspired facials, massages, and body treatments. TOPPER’S restaurant is known for its Retsyo oysters, harvested only 300 yards from the restaurant, and offers transfers to and from White Elephant Hotel’s Brant Point Grill on its 21-passenger boat, Lady Wauwinet. The inn also provides regular shuttle services to the ferry and Nantucket town (about 10 miles away), and outside of peak summer season will drive guests to the village of ‘Sconset in its 1947 Woody station wagon.

Upon your arrival at this 556-room resort, you might be disappointed to find a small pool instead of sandy palapas overlooking the sea. But the Renaissance makes up for its location on a busy thoroughfare in the capital city of Oranjestad with its own private island, a 40-acre oasis dotted with pink flamingos and iguanas. After an eight-minute water-taxi ride, you can choose between two distinct beaches—one adults-only, the other designated for families—plus an array of vacation-friendly amenities. A beachside bar and grill serves up burgers and wood-fired pizzas; an open-air spa offers Swedish and cold stone massages, as well as reflexology; and an extensive water-sports program includes activities like snorkeling, scuba diving, and ocean kayaking. If that’s not enough to tire you out for the evening, a steak house and casino await back at the main resort.

Set on St. Lucia’s westerly Anse Cochon beach, Ti Kaye is a secluded, adults-only oasis that feels worlds away from the rest of the island. Each of the 33 cliffside, gingerbread-style houses feature outdoor showers and verandas with double-wide hammocks, and some even include plunge pools. Since there are no TVs, the focus remains squarely on the picturesque beach, home to a PADI diving center, crashing waves, and breathtaking sunsets. The same is true in the resort’s two open-air restaurants (don’t miss the banana pancakes at the beachfront grill) and treetop spa. Rum connoisseurs can schedule a tasting in Ti Kaye’s wine cave, but if you crave a rowdier scene after all the relaxation, know that it’s a 20-minute drive to the nearest fishing village—you’ll want to make the trek on Friday nights though, when Anse La Raye hosts its weekly street parties.