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Back in the days when there was no road to White Bay, on the island of Jost Van Dyke, boaters would anchor in the bay and swim ashore to belly up to the bar on the beach. They’d pay for their drinks with the cash they’d carried in their pockets—hence the name, the Soggy Dollar Bar. Some patrons still arrive the traditional way, settling in to enjoy the Soggy Dollar’s signature cocktail, the Painkiller, a potent mix of Pusser’s Rum (a BVI brand), pineapple juice, orange juice, coconut cream and a generous grating of fresh nutmeg.

Founded by a surfer in search of the perfect wave, Nihiwatu is a model of sustainable luxury. The resort’s remote location on the jungle-edged coast of Sumba Island lures travelers looking for true escape and the hedonistic pleasures of private, candlelit dinners in a tree house and hikes to cliff-top spas. But it’s the cultural and community experiences that set Nihiwatu apart from other far-flung hotels. Sumbanese villagers make up 90 percent of the staff, and the resort contributes to the Sumba Foundation, which funds health clinics, water wells, and educational initiatives. Guests can observe island traditions, tour the projects, or volunteer at a school lunch program. From $900. This appeared in the Nov/Dec 2015 issue.

Families would be hard-pressed to find a more memorable place to stay than Giraffe Manor. Located in the leafy suburb of Langata, about a 30-minute drive from central Nairobi, the 1932 family home of a former candy baron was modeled on a Scottish hunting lodge before becoming a sanctuary for endangered Rothschild’s giraffes, for which the boutique hotel gets its name. The ivy-clad brick mansion features 12 light-filled guest rooms, many with gauzy canopy beds and understated furnishings, but the real draw is the airy breakfast room, where you can feed the exceedingly friendly animals as they crane their necks through windows and doors in search of snacks. Afterward, complimentary chauffeured vehicles are on hand to take you to the area’s most popular attractions: at the David Sheldrick Wildlife Trust, the residents being fed are orphaned baby elephants.

At Little Italy’s Herb & Wood, Chef Brian Malarkey’s wood-fired dishes include roasted parsnips with pickled raisins, parsley-shallot verde, and molten Marin County brie; roasted beets with sherry, walnut pesto, jamón Ibérico, and burrata; and grilled flat bread with whipped eggplant, za’atar, onions, and pine nuts. But the Mediterranean- and California-inspired menu isn’t the only big draw here: The industrial-boudoir aesthetic is equally inviting, with tufted sofas, soft lighting, and feathery fronds under the soaring ceilings of this onetime warehouse. A charmingly tattered edition of Emily Post’s Etiquette book has pride of place on the hostess stand. But the restaurant is unlikely to call guests on any manners infractions except one. In calligraphy at the bottom of the menu, you’ll find the following note: “Substitutions and additions politely declined.”

Dream about a Caribbean beach bar and chances are you’ll imagine someplace like MooMba, just south of Palm Beach. Here, you’ll find oversize palapas, tiki torches at night, and a crowd looking for fun with their feet in the sand. From its lounge chairs positioned under swaying palms to its extensive list of tropical cocktails, the watering hole is really what an island vacation is all about. To eat, there’s a buffet, with Sunday’s beach barbecue theme being your best bet. Go at happy hour, which is timed to coincide with the sunset, then stay into the evening for live music and DJs.

Near the pontoon bridge in Handelskade in Willemstad, wooden boats from Venezuela dock alongside the canal, and vendors here sell just-caught fish and tropical fruits and vegetables (plantains, citrus, papayas, avocados) directly from the quay under the shade of tents. Mornings are the best time to visit, for the finest selection of produce, the cooler temperatures before the midday sun shines, and the pleasant ambience of the hours before the crowds arrive.

Fifteen minutes south of the Puntacana Resort & Club, Eden Roc at Cap Cana is the most exclusive of the six hotels in the gated Cap Cana Reserve. At this Relais & Châteaux property, guests have their choice of beachfront suites with kitchens; stand-alone suites with private pools, gardens, and verandas; and oceanfront villas that come with butler service. Whichever you pick, you’ll also have access to an oceanfront infinity pool, a 30,000-square-foot spa and wellness center, and a private, Blue Flag–certified beach. There’s even a kids’ club in a lagoon-side treehouse for when adults need some alone time.

When hunger strikes, head to La Palapa for seafood and Caribbean fare, or Blue Grill Bar + Restaurant for Nikkei and robatayaki cuisine. Should you want to venture off-property, know that Cap Cana is home to an 18-hole Jack Nicklaus signature golf course. Bespoke helicopter outings, visits to the Punta Espada equestrian ranch, and days at Scape Park (a natural theme park with attractions like zip-lining and cave expeditions) can also be arranged.

A stalwart on the “best of” lists, this restaurant blends dynamic global cuisine with comfort food… set against a steampunky-sports bar décor. None of this should work, but it very much does. The industrial touches evoke the city’s heritage as a Western working town, as well as its iconic grunge epoch that swept the globe. (The bottle-cap portrait of local legend Jimi Hendrix is especially endearing.) Don’t miss the chicken khao soi, foraged-mushroom pizza with taleggio, or the sublime Vadouvan-spiced carrots with thin curls of feta smoked in-house. The restaurant’s connected to the Kimpton Hotel Monaco and also delivers a mean breakfast, from malted waffles to duck confit hash with cippolini and dried cherries.

Disco ball, lounge, jungle, and cuisine all come together at this trendy restaurant located on Tulum’s main hotel-zone avenue. The venue is renowned for its eclectic style that blends unusual lighting, a lush outdoor setting, and live DJ nights for a cool, hippie-style vibe. Dinner is prepared over open-fire grills and in wood-burning ovens, resulting in flavorful Mexican favorites like taco samplers, quesadillas with epazote, grilled avocado, and slow-roasted pork belly. Gitano also specializes in strange but enticing cocktails from its mezcal bar, like ones that include ingredients like rum, hibiscus, and tropical fruits.

If you’re on your honeymoon or traveling with one other couple, Acacia Villa is a great choice. Priced at around the same rate as a four-star hotel room, but you get the privacy of staying in a home. The villa has an open and airy feel and is built facing east so you get the cooling trade winds the islands are famous for. The only downer is it is on the leeward side of Provo -- on the waterfront -- and not on the beach side. That said, Grace Bay Beach is just a short drive away and you do have your own private swimming pool.

Be Tulum describes itself as a resort, but with 64 rooms and a no-child-under-12 policy, the property feels considerably more intimate than its name and marketing might suggest. The hotel enjoys beachfront status, with powdered-sugar sand inviting guests to do little more than lounge around all day. For those wanting a bit more activity, bikes can be borrowed from the front desk and used to cycle out to the Maya site of Tulum. The spacious rooms—all suites and all at least 500 square feet in size—most of which have either a Jacuzzi or their own pool, as well as polished wood floors and rough, white stone walls.

Psarou Beach is posh rather than party, ringed by upscale hotels and beach clubs and punctuated with a scuba center. The sand is white and the water is turquoise. Restaurants and bars are expensive here, as are the waterside amenities like chairs and umbrellas, but the ambiance is clean and very stylish. Beach dwellers tend to be fit and fabulous so bring your A-game beach attire.

The best of Nicaragua is on the beautiful Emerald Coast. Mukul Resort offers a barefoot luxury experience with stunning suites, exquisite design, and local hospitality. Where else can you surf a great break in front of a 5 star hotel? The Golf and spa are equally as unique.

Isola is Milan‘s sleeper neighborhood because of its great location, hip shops and local vibe. It is also a great area to hang out in because, well, it feels like a neighborhood. Weekend street markets, clever graffiti, cute boutiques, artisanal shops and great bars. Add in there a strong sense of AC Milan fans and lots of people to meet, you’ve got your weekend.

Puente del Inca is a natural bridge located northwest district of Las Cuevas, which has formed over thousands of years by the interaction of extreme temperatures—freezing avalanches and steaming thermal waters. Declared a natural monument, which has been visited by the likes of Charles Darwin, Puente del Inca has five nearby hot springs known for their healing properties. In 1925, the Hotel Puente del Inca was built, each room featuring its own spa; however, it was destroyed by landslides in the sixties and has remained abandoned ever since. Although you can’t bathe in the thermal pools anymore, the striking oxidized rock formations make for a great photo op.