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This elegant bar at the Andaz Maui overlooks tiers of pools, waterfalls, and tropical foliage, all cascading down to the Wailea coast. Hotel guests and visitors alike come here to lounge under umbrellas by day and around a fire pit by night, sipping on cocktails like the Upcountry Buck (white rum, ginger, and pineapple) and the Lahaina Town Fizz (blanco tequila, strawberry, and elderflower). For something unique, try the Silversword, a cocktail designed by legendary Hawaiian mixologist Julie Reiner that features mezcal, sweet vermouth, pineapple, and chocolate bitters. Pair it with snacks like chilled shrimp summer rolls and Thai lettuce wraps, then finish with a ginger ice cream sandwich made in-house.

Sister restaurant to local favorite Serpico’s in Upcountry, this sweet, welcoming spot serves New Jersey–style pizza in an old plantation-style house in West Maui. Tourists dine here, sure, but Prison Street isn’t overrun with overpriced rum cocktails or macadamia-crusted everything. Instead, the pizzeria keeps things simple with subtle nautical decor—a nod to Lahaina’s past as a whaling port—and thin-crust pies in variations like barbecue chicken, Philly cheesesteak, and the Windmills, a curiously named mix of Italian ingredients like pesto, mozzarella, and roasted red peppers. Also available are subs, salads, and calzones, all of which can be delivered if you need a break from dining out one night.

I generally have a thing against beaches next to the road. Usually, they’re unfortunate victims to automotive pollution: obnoxious noises, exhaust fumes, and sneaky greases seeping into everything. Darkwood Beach is different. Sure, it’s right on the road on the southwest coast of Antigua, but somehow it escapes the usual woes of roadside sands. Maybe it’s because the road is fairly quiet. Or maybe it’s the persistent onshore trade winds. Or maybe it’s because people care enough to keep the beach clean. Regardless, what you, the traveler, get is a great beach with good swimming and snorkeling, plus a beach bar serving rum and traditional West Indian eats — complete with white plastic chairs in the sand.

Eat Street Social’s new bar-within-a-bar, the Torpedo Room, serves artisanal tiki cocktails with tasteful kitsch and Midwest flair. Flavors like sweet corn cream (instead of coconut cream) and apple cider (instead of pineapple and orange juice) are termed “Minnesota exotic” for their twist on the classic Painkiller. There are 45 rums to be turned into cocktails and topped with an umbrella or finished with fire, as well as an alcoholic sno cone menu for some added fun.

Hotel Atarazana is a simple, airy, and clean hotel a stone’s throw from Plaza España at the north-east of Santo Domingo’s Zona Colonial. There is a cute walled courtyard where you take breakfast, and an open rooftop (with some shade) for sunbathing, reading, and rum; drinking water is included; and the staff are friendly and some speak English. All the Zona Colonial’s sights are within easy walking distance; the pedestrianized El Conde is a ten minute saunter south. (Note: The hotel is so close to the bars / clubs off Plaza España that it can get noisy at night.)

Just next door to crowded Doctor’s Cave Beach in Montego Bay is a quiet and spacious stretch known as Cornwall Beach. You won’t see more than a couple of people at a time here during the week. Late afternoons and weekends attract a few locals who come to relax and enjoy the restaurant and bar. A small entry fee—under US$5—covers the on-site facilities, including lounge chairs and snorkel gear. Cornwall Beach occasionally hosts a sunset beach party on Sunday afternoons with a “bottomless” Appleton mug option (that is, all-you-can-drink rum).

The Dubai Spice Souk is a traditional market located in Deira, near the famed Gold Souk. It’s easy to overlook the Spice Souk if you’re not looking carefully; tucked into alleyways off of Baniyas Street, the souk is small, but manages to pack a pungent punch. If you plan on purchasing spices – from cardamon to cumin to turmeric to nutmeg, and everything in between – be prepared to haggle. A good rule of thumb is to cut the vendor’s opening salvo in half, and then barter upwards from there until you reach a number you’re both comfortable with.

A dream retreat for horse lovers, the 240-acre estate is 45 minutes from London and has an equestrian center and polo fields. Game of Thrones Keep an eye out for Prince Harry playing a match on the polo grounds. Competitions are held from April through September. Learn from a Pro Coworth Park works with the Guards Polo Academy and Andrew Hine, the former captain of the England Polo Team, to provide lessons. Serious riders can enroll in a three-day elite polo academy. Recovery Drink The Bar at Coworth Park has started mixing polo-inspired cocktails. Try the rum-and-brandy-based Under the Neck, named for the most difficult shot in the game. Rooms from $370. Polo lessons from $255. 44/(0) 1344-876-600.

A former 18th-century bishop’s palace in Korčula Old Town, this Relais & Châteaux property has been meticulously restored into an all-suite luxury hotel. Each of the five rooms is decorated along a different theme inspired by the Silk Road and the explorer Marco Polo, who is rumored to have been born on Korčula. The two-bedroom China Suite features low-slung furniture, red pillows, and a scene-stealer of a terrace with views across the town and coastline, while the one-bedroom Arabia Suite includes an all-white color scheme and intricately carved wood screens.

The hotel’s LD Spa specializes in Thai and Ayurvedic treatments, and the restaurant serves fresh, local seafood on a long terrace above the Old Town wall. The restaurant also produces three different olive oils from the groves around Korčula, and works with local partners to serve wines made from indigenous grapes like grk and pošip.

Founder’s Note: Travel Like an American

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.

Dasheene, the restaurant in the award-winning Ladera Resort, is a magical place unlike any other on the island. The open dining room, overlooking the sea, is so close to the Pitons that you feel as if you could reach out and touch the peaks. The menu, which focuses on ingredients sourced from local farms and plantations, puts a creative spin on classic St. Lucian cuisine, including plantain gratin with a coconut rum sauce, and roast conch. The restaurant is open for breakfast and lunch as well, but there’s no beating the romantic atmosphere and sunset views at dinner, which make a meal here well worth the high price.

The Electric Pickle is a boutique entertainment and music venue located in downtown Miami‘s Design District/Wynwood area. This area is the most popular location for those wanting to escape the velvet rope of South Beach. The beats pump inside the diverse bar filled with crowds from every Miami background. The Pickle was named #8 Bar that Rocks by Rolling Stone. If you like to dance, this is the place. Celebrity DJ’s take the stage from time to time and there are always specials on drinks. Step away from your regular rum and coke to try one of The Pickle’s specialty drinks, they are full of flavor and fresh ingredients.

A breezy little beach hotel filled with rough wood, natural linen, and flea market finds, the Rose seems, to the uninitiated, like a pure product of quirky Venice’s hipsterfication. In fact, the historic, wood-and-stucco building was built by the beach town’s founder, Abbot Kinney, in the early days of the 20th century; rumor says it was his private brothel, frequented by such friends as Charlie Chaplin. By the 1970s, at the height of Venice’s drug culture, the building had become a flophouse of sorts, and neighbor Dennis Hopper was known to drop by. Before two British photographers discovered it, the house had turned into a mural-covered crash-pad for surfers, yogis, and beach bums of all kinds.

Looking at the low-key Rose now—the town’s first true boutique hotel, barely half a block from the beach—one would hardly know that the entire history of Venice had passed through it. The rooms are spare but stylish, with large windows, art photography, and vintage furniture. Some rooms are large enough to live in, whereas others share a hallway bathroom. Amenities are minimal—Stumptown coffee, bicycle rentals—but a relaxed beach house that attracts artists and creatives looking to delve into Venice’s eclectic, vibrant culture doesn’t need to try too hard to be cool.

With its striking white facades and terra-cotta rooftops, you might mistake Cap Maison for a Mediterranean villa on the Costa Brava. However, this all-inclusive resort set on a former sugar plantation on St. Lucia’s north coast offers more than meets the eye. The pastel-hued interiors are matched by the sunny dispositions of the superb staff, who cater to every request, whether it’s finding a shady spot by the terraced pool area, booking a paddleboarding excursion off the private beach on Smuggler’s Cove, or arranging for the house yacht to take you to the neighboring island of Martinique for the day. Don’t miss the sunset views at the Cliff at Cap restaurant, where locally sourced dishes like reef conch ceviche and passion fruit soufflé are topped off with some of the resort’s house-made rum.