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Perched 300 feet above the Pacific on 15 verdant acres, Hotel Wailea is a former members’ club that still feels like a hidden enclave of cool. In 2014, new owners invested $15 million in a redesign that left 72 one-bedroom suites with white oak floors, Sub-Zero appliances, and Hawaii-inspired art. Still, it’s the pool that really wins over guests—it’s calm and quiet (thanks to the hotel’s no-kids policy); there are umbrella-shaded loungers and bungalows with fans for when you’ve had too much sun; and the beyond-gracious staff are always at the ready with water, cocktails, kombucha, and coconut water. The hotel lounge offers free wine and appetizers at 5 p.m. on Friday nights, while the farm-to-fork restaurant highlights produce grown in the resort’s own garden. Complimentary on-site activities include yoga, outrigger canoeing, and mixology classes, but guests can take the hotel’s Tesla Model X house vehicles anywhere in Wailea or rent an electric bike and cruise the South Maui coast if they want to get off property.

From the porte-cochère entry at the Westin Puntacana Resort & Club, you’ll catch an inviting first glimpse of coconut palms, manicured grass, and a long swimming pool that seems to end at the sea. The view only gets better upstairs, where all 200 rooms—including 16 suites—offer swoon-worthy ocean vistas. On the hottest of days, the high-ceilinged, open-air lobby is a great place to hang with a cold one while catching the ocean breezes. When it’s cooler, have lunch by the pool or at the beachside La Palapa, and plan for dinner at the open-air Brassa. As a guest at the Westin, you also have access to Puntacana Resort & Club’s eight restaurants, two golf courses, tennis center, Six Senses Spa, aquatic center, and Grupo Puntacana Foundation activities.

Located in the heart of Whalers Village on Kāʻanapali Beach, Hula Grill is a busy hangout with live music seven days a week. You can sit for a meal in the open-air dining room, but the real party happens at the restaurant’s Barefoot Bar, right on the water’s edge. Kick off your shoes and sink your feet in the sand, then order a Barefoot Brew (made specially for the bar by Maui Brewing Co.) or cocktails like piña coladas, mojitos, and Maui Mules with organic vodka. Also on offer are a range of non-alcoholic drinks, from house-made sodas and fresh-squeezed juices to local kombucha and pure coconut water, as well as a solid food menu that highlights Hawaiian farmers and fishers. For a great deal, head here for Aloha Hour, which takes place daily from 2:30 p.m. to 5 p.m. and includes special prices on pupus and drinks.

Unlike most people who arrive at the property fresh off a plane and short cab ride, I showed up after spending an hour searching for waterfalls on horseback in the Samana wilderness. Basically, I was tired, smelly, dirty… And by no definition sublime. The moment I walked into the shady, chic reception area, everything changed. I was immediately relieved of my bulky, mud-splattered belongings by practiced staff and my newly emptied hands were then wrapped around a fresh coconut. At first, you might think the stylish surroundings would clash with such local, earthen niceties, but you’d be wrong. Sublime makes an art out of weaving local and luxury together in almost every aspect of their experience. In the three-story main building, 50 one- and two-bedroom Suites (16 for guests, the rest privately owned) form an arc around the property’s centerpiece: a sheltered and soothing pool area that’s a mix of interconnecting canals, larger pools for swimming, beds wrapped in billowing fabrics, grassy expanses and simple walking paths. This place is truly Sublime!

Why we love it: A condo-style property near Pier 60 that’s perfect for traveling families

The Highlights:
- Spacious, residential-style rooms with kitchenettes
- A kids’ club for children and rooftop cantina for adults
- A prime location steps from the Gulf and Pier 60

The Review:
Steps from the ocean and famous Pier 60 stands the flamingo-pink Hyatt Regency, favored for its friendly, attentive service. A residential-style property, the hotel boasts 287 generously sized rooms and suites, complete with some combination of walk-out balcony, kitchenette, dining table, living area, and workspace. Also on site is a 24-hour gym, a serene spa with sun-warmed shell massages, and a heated pool on the eighth floor overlooking the beach.

Though rooms here cater to those who like to prepare their own meals, the hotel still shines with dining options. Guests can start the day with freshly brewed coffee and pastries from the grab-and-go Market and end it with a handcrafted cocktail at Off SHOR or the Latin-inspired Tropicana Rooftop Cantina (order your drink in a souvenir glass and it will come in a coconut carved into a monkey’s head). For dinner, there’s SHOR American Seafood Grill, which boasts a spacious patio and regional seafood dishes like whole local snapper and line-caught Florida swordfish.

Roseau’s only oceanside dining option, the elegant Palisades pairs sweeping water views with one of Dominica’s best culinary experiences. Here, creative dishes showcase the island’s natural bounty, including produce sourced from local farms and fish straight from the Caribbean Sea. Start with dishes like BBQ jerk octopus and sesame-crusted tuna with a soy-chili dip. Then, move on to the lion fish, served with green-banana croquettes and mushroom sauce. Fancy something lighter? Try a lentil-black-bean cake or callaloo soup, made with baby taro leaves, coconut milk, yam, and green bananas.

Why we love it: An all-in-one café, restaurant, and boutique hotel for the design-minded traveler

The Highlights:
- A restaurant run by a James Beard Award–winning chef
- Complimentary breakfast from the bakery delivered to your room
- Excellent design featuring local wares

The Review:
What started as a contemporary eatery in 1999 transformed into a bakery, restaurant, and boutique hotel in late 2016, when it took over the adjacent Dunn Brothers coffee shop as part of a major expansion. Today, guests are drawn to Alma as much for its acclaimed bar and restaurant as for its seven uniquely designed guest rooms, done up in all-natural cotton bedding, handwoven wool throws, and vintage rugs from Aubry Angelo. The bathrooms are impeccable as well, with spacious, white-and-brass-tiled walk-in showers and organic bath products from Bespoke Body & Wellness.

Every stay comes with complimentary room-service breakfast from the on-site bakery, meaning guests don’t even have to get out of bed for house-made pastries like lemon-currant scones, chocolate croissants, and blueberry Danishes. Come evening, head to the award-winning bar for expertly made cocktails like the Spritz Life (made with Cappelletti, prosecco, and chocolate-infused orange bitters), followed by dinner in the restaurant, which offers a three-course prix fixe menu with seasonally inspired dishes such as chestnut bread pudding with Maine lobster, and duck two ways with coconut-braised kale and spiced cashews.

If your dream vacation involves the ultimate in luxury, the St. Regis should be at the top of your list. The 151 rooms feature hand-crafted chandeliers, original artwork, and macassar ebony furnishings, as well as Italian marble bathrooms that have soaking tubs and TVs hidden in the mirror. But the real draw is the service: All guests have access to the butler desk, which can fulfill requests both big and small, from unpacking your suitcase to delivering the morning newspaper, and designated pool chamberlains mist guests with Evian and deliver frozen-fruit skewers and coconut water at the 40,000-square-foot Pool Piazza, complete with red-striped chaises and waterside bar. While the promise of massages in the Remède Spa and afternoon tea in the English-style Astor Court make it hard to leave the resort-like premises, the hotel’s location a five-minute walk from the Buckhead shopping complex may sway you. And if you need help hauling your spoils to your room, remember there’s a butler waiting just around the corner.

The Southernmost Point buoy, at the corner of Whitehead Street and South Street, marks not only the spot for the southernmost point of the continental United States but also the distance (90 miles) to the next country, Cuba. The buoy, installed by the city in 1983, is visited by thousands of people each day. (Before the buoy, a small sign stood at the spot alongside a line of seashells for purchase.) Taking a photo in front of the buoy is imperative for a first visit to Key West, so bring a tripod, or ask a stranger to snap a few shots. Buskers play music, and street vendors sell food and goofy souvenirs and slash open coconuts to drink.

Anyone who has been to Brazil knows that the country has fantastic open-air markets, known as feiras in Portuguese. They often feature a combination of handicrafts, antiques, live music, dancing, and street food. The market on Saturdays at Praça Benedito Calixto in São Paulo is no exception, but this one is almost unknown to tourists. Older Paulistanos (as Sao Paulo residents are called) sell beautiful antiques that reflect the city’s cultural ties to Europe. Artisans sell colorful woven clothing, handmade leather shoes, jewelry made from açaí seeds, baskets and mobiles made from recycled magazines, and much more. In the center of the market is a square of food and drink vendors, selling food from Northeastern Brazil, dried fruits, coconut water, and other typical Brazilian street food. In the early afternoon, live chorinho music begins and the square soon fills with people dancing. This outdoor market is much more than a place for people to shop—it’s a place for people to relax and have fun. The market runs every Saturday 9:00 a.m.-7:00 p.m. The streets surrounding the market have many good restaurants, and the neighboring street of Teodoro Sampaio is known for its shops selling traditional Brazilian musical instruments. There are parking garages nearby; the market can also be reached by bus or by subway (Clinicas station).

With its chill vibe, funky decor, warehouse-like interior and spacious terrace, Pacific Parc is a rock ‘n’ roll bistro with an edge. Situated in a former treatment plant at Westergasfabriek, the café-nightclub on Amsterdam‘s west side clearly represents its mantra, “Do not beg for the right to live, take it.” Life is good over international favorites like satay with coconut-peanut sauce, Indian lentil curry, Black Angus burgers and Dutch pannenkoeken, all priced under €20 on lunch and dinner menus. For kids, chicken drumsticks, chips, cucumber and ice cream are on a children’s menu for €8. While little ones romp on the spiral staircase, you can dine at the bar or at wooden tables in the open-zoned dining area, under a whimsical chandelier hanging from the sunroof. If you’re attending a Westergasfabriek event, Pacific Parc is a great place to meet up with friends. But there’s more to this place than relaxed ambiance, good drinks, reasonably priced fare and a menu based on seasonal ingredients. Thursday through Saturday, DJs mix hip-hop with disco and swing tunes. By 23:00, dinner seats are pushed aside and anyone who sticks around may be in for a wild night. A special “Dinner and a Movie” deal entitles you to a flick at Ketelhuis, Westergasfabriek’s cinema, plus a starter and main course (excluding drinks) at Pacific Parc for €25. While the restaurant may lack for romance, it’s a fine place to get your weekend date off to a savory start.

West Randolph Street in Chicago’s West Loop has become a new home to the city’s culinary talents. Stephanie Izard first drew crowds cooking dishes like roasted pig face at Girl & the Goat (the restaurant pictured above). She then opened Little Goat, a retro diner, across the street. Graham Elliot Bowles keeps it simple at his casual g.e.b, where each dish has no more than three ingredients. On a more elegant note, the prix-fixe menu at Grace, from chef Curtis Duffy, features dishes such as kampachi with coconut, lime, basil, golden trout roe, and pomelo presented in a cylinder of frozen ginger water.

Mexico City has no dearth of luxurious boutique hotels, but Las Alcobas is a special option. Designed by famed firm Yabu Pushelberg, the hotel is full of gorgeous details, from hand-stitched leather wall coverings to a spiral staircase that surges up from the lobby. Upon arrival, guests enjoy a welcome drink as a bellman leads them to their room; explains the technology that controls the light, sound and temperature; and offers them a selection of handmade soaps. Once settled in, they can lounge in plush robes on their goose-down comforters while sampling snacks from the minibar. For a heartier meal, Las Alcobas offers two excellent restaurants. Just outside the hotel’s front door, there’s also Presidente Masaryk, Polanco’s main avenue full of restaurants and high-end boutiques.

Fleetwood Mac front man Mick Fleetwood is behind this bar and restaurant, located on a third-floor rooftop in Lahaina. Here, guests sip drinks under beige umbrellas while taking in views of the dreamy blue Pacific. To pair with award-winning cocktails like the Heart of the Jungle (Cynar, Velvet Falernum, coconut rum, and lemon juice), which comes in a tiki artichoke, executive chef Eric Morrissette serves a menu of elevated bar bites, fresh local fish, and meatier dishes like filet mignon with peppercorn reduction. If you’re not a cocktail person, know that the robust drink menu also features beers from Maui Brewing Co. and Kohola Brewing as well as exclusive wines like Krug Brut from Reims, Luberri Gran Reserva rioja, and even a Chateau Musar red blend from Lebanon.

With its 26 suites, private beach, and two waterfront bars, Calabash Cove offers a boutique hotel alternative to the typical all-inclusive experience. Set a stone’s throw from the turquoise waves of Bonaire Bay, the sprawling, Balinese-inspired Water’s Edge cottages are the ones to book thanks to private plunge pools, outdoor rain showers, and patio hammocks positioned to highlight superb sunsets. The resort’s remote location ensures tranquility, as does the spa, which offers in-room treatments using ingredients sourced from St. Lucia’s floral and culinary bounty. That abundance is also on display in the Windsong restaurant, where local dishes get an elegant twist (octopus tempura, smoked coconut crème brûlée) in a terrace dining room with the ultimate ocean backdrop. Follow your meal with a brief walk down Calabash Cove’s small boardwalk and stop to spot shooting stars in the dark skies above.