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  • 390 S Church St, George Town KY1-1106, Cayman Islands
    Though it lacks a beach, this family-owned and professional diver–managed resort on the rocky coast just south of George Town has direct ladder access into the Caribbean. Grand Cayman’s two famous underwater sites, Eden’s Rock and Devil’s Grotto, are just a short swim away, and boat trips offer the option of two daily dives (including night dives). Images by some of the world’s most respected underwater photographers decorate many of the tiled and comfortable smoke-free rooms, some of which have kitchens and private balconies or terraces. The vibe is laid-back; post dive, guests sit by the pool or swap stories at the palapa bar, which has the island’s best sunset vista. Managers Anne Briggs and Lisa Evans, the granddaughters of Sunset House’s founders, make sure everything runs smoothly and ensure visitors explore the best of Grand Cayman both on shore and underwater.
  • 47 Main Rd, Green Point, Cape Town, 8005, South Africa
    There’s a touch of Old World glamour to the Cape Royale—the imposing facade, the dramatic lobby, the bellmen in top hats—but just when you start to wonder if the whole experience is going to be resolutely old-school, you’ll find yourself pleasantly surprised by the sleek rooms. They feature contemporary furniture, granite and porcelain bathrooms, and a soothing palette of mostly grays and whites with the occasional punch of lime green or aqua blue. It’s also the site of six restaurants, cafes, and bars, each with its own theme, from Italian cuisine to healthy eating to Thai or Middle Eastern fare.

    The city’s best beaches and nightlife—not to mention Green Point’s dazzling Cape Town Stadium, erected for the 2010 World Cup and now the site of many a mega-concert and local soccer match—are minutes away.
  • Unnamed Road, The Bahamas
    It is not quite accurate to say that this 13-room beachfront property on sparsely populated South Andros Island is off the beaten path. Sure, there are no roads to bring you here, and the only neighbors are the denizens of the 125-acre nature preserve that surrounds it, but a seaplane flight from Nassau will have you wading ashore in just 15 minutes. Once settled into their thatch-roofed private villas, guests gravitate toward the Great Room for fruity drinks, fresh-caught meals, and tall tales. While there is every kind of watery diversion, from bonefishing to scuba diving—and nature tours, too—it’s the kind of place where kicking your feet up is the most strenuous thing you’ll do all day, and where privacy is so valued that beach butlers won’t intrude unless, in one of the older nautical traditions, you raise a flag to indicate that you require food and drink.
  • 61 Pitts Bay Road, Pembroke HM 08, Bermuda
    Built in 1906 as a private residence and converted in the 1950s, Rosedon Hotel is a low-key alternative to Bermuda’s pricey chain hotels. Despite being located in the bustling heart of Hamilton, the property’s lush tropical gardens have the feel of a country estate where geraniums always seem to be in bloom and balmy breezes waft through elegant, colonial-style rooms. The 40 individually appointed accommodations have enough chintz to please a dowager aunt, plus iPod docking stations and private balconies to satisfy everyone else in the family. Laid-back pleasures await in the public spaces: sample weekly changing finger sandwiches during afternoon tea or dine on fresh-caught specialties at Huckleberry, the on-site restaurant, or simply lie in the sun on one of the white chaises that surround the small pool. Though the resort doesn’t have a beach of its own, a free shuttle is on hand to take you to pink-sand shores nearby.
  • Freeman's Bay, no 1, English Harbour, Antigua and Barbuda
    Even during Antigua Sailing Week, when English Harbour is chock-a-block with yachts from all over the world, the 28-room Inn at English Harbour remains serenely detached from the chaos. The inn is five minutes by water taxi from the center of things at historic Nelson’s Dockyard, but its tucked-away location on a white-sand beach backed by 19 leafy acres (and a no-kids-under-10 policy) ensures tranquility. Four snug rooms, with marble floors and queen beds, occupy two beachside cabanas, while 25 more generously proportioned suites, all with dark mahogany floors, four-poster king-size canopy beds, and verandas or balconies, are in three wooden buildings sitting farther back among the tropical greenery. Although the Terrace Restaurant and Stone Bar are in the property’s original stone house, the rooms, despite their colonial look, are relatively modern, which means there is a flat-screen TV, an iPod docking station, and Internet access.
  • Av. Los Flamingos Y, 16 De Marzo, Puerto Villamil 200250, Ecuador
    This top-of-the-line property of the San Vicente Hotel Group (which owns the nearby San Vicente and Hostal Villamil), is a three-level, all-white hotel that feels almost like a beach villa. It’s actually just a couple of blocks from Puerto Villamil’s two-mile-long stretch of municipal sand, and most of the surrounding sandy streets are filled with palm trees. The facilities here provide enough so that guests’ only real concern will be getting to other parts of the island. The restaurant stays open all day with a varied menu and drinks list. There are flat-screen TVs in the rooms and free Wi-Fi in common areas. Shaded by a few umbrellas and a cane canopy over the Jacuzzi, the rooftop terrace is the favorite hangout for most guests at this small hotel. In every direction comes another jaw-dropping view, such as the Pacific Ocean, the Sierra Negra Volcano, the highlands, or a saltwater lagoon filled with flamingos.
  • Negril, Jamaica
    A signature experience in Negril is to go on a two-hour glass-bottom boat snorkel trip, toward the cliffside or to the nearby reef around Booby Cay. Truth be told, snorkeling isn’t a must if you’re not up for it—but floating on a small boat amid deep jade and turquoise waters and being able to see marine life 20 feet or more below through the glass is a memorable experience. If you do want to snorkel, the cliffside has stunning limestone formations and underwater caves, while the reef is filled with all sorts of marine life, from stingrays to barracuda. A glass-bottom boat ride shouldn’t cost you more than US$20 per person. Look out for Famous Vincent‘s boat—the best pick—or approach one you see resting along Seven Mile Beach, across any reputable resort. The boats—including Famous Vincent—occasionally ride along the cliffside resorts in the mornings or afternoons, looking for anyone interested in an impromptu adventure.
  • 1 Tropical-Islands-Allee
    Though not really a tropical island, the indoor resort called “Tropical Islands” outside of Berlin makes for a great (albeit unusual) day trip. Located inside a former Soviet air hanger, the building has been converted into a biosphere with a tropical climate. Inside the resort there is an artificial beach, swimming pools, saunas & a spa, water slides, a small rainforest and even a hot air balloon! To get there with public transporation, you can take a Regional Express train from central Berlin. Trains leave every hour toward Cottbus (depart at Brand-Niederlausitz). It takes about 50 minutes. From the train station, Tropical Islands offers a free shuttle bus for the 5-minute journey to the resort. If you buy tickets at the door, admission to the Tropical World or the Tropical Sauna & Spa complex is 34.50€ for adults and 27€ for children age 6-14. A Kombi-Ticket is valid for both areas and costs 39.50€ for adults and 27€ for children.
  • Les Salins
    Even with the summer crush on the French Riviera in full swing, there are quiet escapes to be found. In particular, I like to take walks along the Sentier du Littoral, the coastal footpath that stretches the length of the French Mediterranean coast. My favorite segment is in St. Tropez, where I head by boat from Ste. Maxime (the Bateaux Verts leave every 10 minutes). From the ferry landing, I start walking—through the narrow streets and old port, under the imposing citadel that has guarded residents since around 1600, past the cemetery, and onto a narrow path that ribbons around the St. Tropez Peninsula. The 7-mile route takes me by inlets of crystalline water, hidden villas whose residents I always wonder about, and past dozens of little beaches that are significantly more serene and less crowded than the frenzy of those found along Pampelonne Bay, where this piece of the trail ends. You can hoof the two miles back to the village, or take the bus.
  • 3876 Noriega St, San Francisco, CA 94122, USA
    This bakery just opened across the street from Woodshop. It’s a godsend. It’s been rough finding good coffee out here, but they serve Blue Bottle Coffee and breakfast sandwiches on house-baked biscuits.”
  • Barnes Bay, West End 2640, Anguilla
    Four Seasons might have spruced up the property slightly when it took over management from Viceroy in 2016, but the original clean lines and sharp angles of the midcentury modern architecture coupled with Kelly Wearstler’s playfully eclectic interiors are still unmistakable at this stunning property overlooking Meads and Barnes bays. Epitomizing tropical modern luxury, the property is awash in marble, natural stone, and wood, with dramatic views of the Caribbean Sea from dining rooms and infinity pools that seem to hover from their cliffside perches. Spanning 35 acres, the resort is home to 166 spacious, serene, and stylish accommodations ranging from suites to townhomes and private villas. Indulge at five dining venues, including the aptly named alfresco Sunset Lounge for sushi and the fine-dining Cobà, where fresh seafood is paired with choice cuts of meat and an impressive wine list. With three swimming pools and two distinct beaches to choose from, the most stressful part of the day is deciding where to lounge.
  • Jumby Bay Island, Antigua and Barbuda
    A private-island resort six minutes by boat off the coast of Antigua, Jumby Bay is one of the Caribbean’s top luxury, all-inclusive stays, and one of its most environmentally aware. A $28 million renovation in 2010, which included the addition of 28 suites and a first-ever spa, gave it all the digital-age essentials: 42-inch flat-screen TVs, iPod docking stations, Bose sound systems, free Wi-Fi. Yet its underlying spirit of environmental responsibility, highlighted by its hawksbill sea turtle preservation program and its banishment of wheeled vehicles except for golf carts and bicycles (every room comes with two bikes), continues to reign. Rosewood manages the resort, but it belongs to an association of island homeowners, some offering their properties for rent. So if, say, a 1,346-square-foot beach-view pool suite isn’t big enough, it is possible to do as celebs such as Hillary Swank, Jim Carey, and Paul McCartney have done and plop down up to $20,000 per night for a private villa or estate home. Couples can be perfectly content here, but it is especially attractive to families, who appreciate programs like the Rose Buds kids’ club.
  • 5000 Kahala Ave, Honolulu, HI 96816, USA
    Long considered one of the top hotels on Oahu, the Kahala has always been a particular favorite among the type of guests who travel with their own security detail. A number of past U.S. presidents, plus kings, queens, princesses Grace and Di, a handful of Nobel Peace Prize winners, rock stars, and movie stars, all have slept under its venerable roof at some point during the hotel’s 50-year history. The see-and-be-seen set moved on long ago, but privacy seekers still make a beeline here. They’re drawn less by the property’s fabulous beach (though that’s reason enough to stay here) than by its exclusive location—in a well-fortified cul-de-sac in the ritzy Kahala neighborhood. But there’s a warm and fuzzy side to the hotel, too. A pod of dolphins has full-time residency in the hotel lagoon, and visitors of all ages can swim with them (for a fairly steep fee). Rooms have a preppy beach house vibe—raffia ceiling fans, linen loveseats—and many come with heart-stopping sea views.
  • A tiny, man-made island in Clifton Harbour built with discarded conch shells, Happy Island is really just a small bar where you can tie up for a while and have a drink, a meal, and a conversation with Janti Ramage, the island’s joyful builder, owner, and operator. Just be sure to call ahead, as Ramage keeps flexible hours.
  • Liberia Guanaste 26Km al Norte del Doit, CR-G, Peninsula Papagayo, 05000, Costa Rica
    Especially after its recent $35 milllion refurbishment, Four Seasons Costa Rica sets the standard for service and luxury in Costa Rica’s burgeoning luxury resort market. Its location is unmatched: perched atop a narrow isthmus, overlooking beaches on both sides, at the very tip of the Papagayo Peninsula. Three swimming pools form the hub of action, spanning the width of the peninsula; on one side of the enormous main pool is an adult pool leading to serene Playa Virador on the Pacific, while the busier family pool leads down to Playa Blanca, where most of the water activities happen—snorkeling, stand-up paddling, kayaking. There’s also an 18-hole Arnold Palmer–designed golf course that’s been tamed from the surrounding jungle. Guest rooms have marble baths, and outdoor terraces or verandas, while the larger suites (one- and three-bedroom) include their own pools. For light dining options, try the ceviche offerings poolside at Bahia or Italian seafood at Pesce. For a splurge, head to Caracol at the golf course for steaks and lobster tail.