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Most of the year, Punta Cana’s white, sandy stretches of sand are blessed with gently lapping surf, which means that night swimming isn’t as dangerous or daunting an exercise as it can be on other Caribbean islands. Slip into the water near the Westin’s covered pier, and have the ocean all to yourself. Under the bright light of a full moon, you might even catch a glimpse of a sea turtle inching its way along the beach.

Negril, or the “Capital of Casual” as it’s known in Jamaica, is everyone’s favorite getaway, from locals to the visitors who return year after year. The buzz of activity on Seven Mile Beach’s powdery white sands is tempered by the breathtaking, serene views of the West End’s cliffs towering over the Caribbean. Lots of bars, hotels, and restaurants line Seven Mile Beach, and local eateries and smaller boutique resorts are perched up on the cliffs. While there’s more hustle and bustle and throngs of tourists on this end of Jamaica, the region still offers many secluded spots and unique experiences.

Saline is the most beautiful and the most famous beach in St. Barths. From the shore, you cannot see any building: no fancy bar, no posh restaurant, nothing. Just the wild beach and you. Saline Beach never really gets crowded, as the island is too small to have actual crowds. But it is a true luxury, early morning, to come there for a nice swim. More than once, I’ve been able to be the only one there. This long, beautiful, renowned beach was just mine! It is okay to do nude sunbathing in Saline, but it’s better if you do it on the far sides of the beach. Indeed, the middle part is where the trail arrives from the parking lot and you do not want to make families feel uncomfortable. Even if nobody really cared. Again, early morning, it is just a couple of people here and nobody minds if you swim naked in this pure Caribbean blue water. Vive la liberté ! My tip: Bring a bottle of water if you are planning on staying for long, as there is no store on the beach. Nothing!

Belize’s liveliest time of the year comes in September, when the entire country celebrates independence for three entire weeks leading up to Sept. 21. The major towns and cities host various events, and a countrywide calendar is published on Sept. 1, allowing you to follow along with the fun wherever you might find yourself in Belize. The most popular events are a steel pan concert called Pan Yaad, held in Belize City, and two full-blown carnival parades. Belize City Carnival, with soca and Caribbean music blaring, is held in mid-September, while Orange Walk Carnival takes place on Independence Day and celebrates Mestizo heritage. Take advantage of low-season fares to get a unique culture-filled experience in Belize in September.

While most of the Grenadines’ most luxurious hotels cater to the one percent, Salt Whistle Bay, on Mayreau, offers a blissfully pared back—though no less exclusive—experience. You’ll feel like a modern-day Robinson Crusoe when holed up in one of the 22-acre property’s eco-friendly bell tents or stone bungalows, each outfitted with colorful rugs, fans, and plush linens, and positioned to capture ocean breezes. By day, swim with sea turtles, sting rays, and tropical fish in the surrounding reef-filled waters—snorkeling masks are free to guests, as are stand-up paddleboards—or try kiteboarding on the resort’s designated beach. By night, share those adventures over a dinner of grilled lobster at the on-site restaurant and bar.

Located on the northwest point of the island, Aruba’s only golf course offers views across the ocean and desert. It’s also independent, meaning guests at any resort can use the championship greens, which were designed by Robert Trent Jones II. Visitors to the course have access to club rentals as well as a putting green, a chipping area, and swing tutorials with a high-tech simulator. Note: Aruba’s constant trade winds present a challenge to even the most experienced golfers, so prepare for a somewhat frustrating game.

Before I went to Belize, anyone I spoke with who had already been told me that I had to have a meal at Elvi’s Kitchen. What started out as a take-out burger window in 1974 eventually became a sit-down restaurant serving lovingly prepared Caribbean dishes such as conch soup and fritters, mojo de ajo, fried green plantains, and street corn. During high season you might have to wait in line to eat dinner at the restaurant, but most of the time, there isn’t much delay. Save room for dessert. Elvi’s Kitchen is open from 11 a.m. to 10 p.m., Monday through Saturday.

Bypass the roadside watering holes and take a boat ride to Floyd’s Pelican Bar, instead. This thatched hut stands on stilts out in the water, making it a dreamy spot for an afternoon of swimming and shooting the breeze, solo or with friends. It’s 30 minutes from Treasure Beach (arrange a boat ride through your guesthouse or resort), and you can arrive for lunch and stay until after sundown for the just-caught fish, rum, and chilled Red Stripe on the menu. Inside the tiny shack, the flags of various countries hang and previous customers have left messages scrawled on planks and benches. Sit outside and watch the pelicans flying in formation across the horizon.

What do you get when you combine a design gallery/store with a café, beauty salon, fashion boutique and rental apartment? Add it all up and it equates to Droog, a multifunctional space that melds a 160-square meter exhibition space with an airy dining room, a tearoom overlooking an outdoor garden and a single bedroom for overnight guests. “The concept of a hotel has been reversed,” says Renny Ramakers, co-founder and director of Droog. “Whereas a hotel is...mostly about sleeping, here we have enlarged and emphasized all the aspects that many hotels also offer and made them central to the experience—and it even has a room to sleep in.” Housed in a 17th century building in central Amsterdam, Droog showcases product design in exhibitions and lectures, and invites people to plug in as they choose. In the gallery, view the latest in international furniture design, art and fashion. Shop at the Droog Store, then refuel at RoomService by Droog, open for late breakfast, lunch, high tea and early dinner, or just drinks and snacks. Head to Cosmania to up your beauty game, shop for hip fashion at Kabinet and stock up on wellness products at Weltevree. On top floor, Hôtel Droog offers overnight guests a brightly-lit bedroom, bathroom with separate bath and shower, living area and kitchen. Perched in the aery enclave, enjoy a splendid view of Amsterdam rooftops and the city below.

On a hopping night, Noorderlicht (Northern Lights) blazes with colorful lights visible clear across the IJ River—hence its name. For those drinking and jamming to live music on a waterfront terrace warmed by a roaring bonfire, the setting is more intimate. We’ve reached Noorderlicht, a “cultural café” in Noord-Amsterdam, via free ferry from Central Station. Destination: NDSM yard, a revitalized shipyard that belies its maritime/industrial heritage with warehouses and shipping containers transformed into nightclubs, hotels and student housing. Dotted with fishing villages, condos and restaurants, the eclectic neighborhood calls itself “Art City.” With its airplane hangar shape and greenhouse-like architecture, Noorderlicht enhances the funky landscape. The popular café draws creative types who come for waterfront dining, drinking and dancing. Inside, warm-hued wall hangings, wooden flooring, tables ornamented with polished driftwood and a disco ball contribute to an inviting ambiance. Seasonal lunch and dinner menus feature organic and regional dishes, plus casual fare like frites and burgers. Noorderlicht’s grassy terrace offers a spectacular view of Amsterdam city center from the other side of the Ij River. Dine on wicker chairs, cushioned couches and picnic tables as musicians perform overlooking the waterfront. A roster of events ranges from campfires and poetry readings to DJ nights that usually inspire some pumping and grinding in a young, energetic crowd.

From its new location on the Singel, Supperclub maintains the old traditions of one of Amsterdam’s most innovative nightclubs. In few other upscale restaurants can you take off your shoes, get in an oversize bed with friends, and savor an unconventional five-course meal over the course of an evening. But supperclub is not for everyone. Part culinary journey, burlesque/vaudeville club, cocktail bar and experimental free state, it’s a unique if somewhat pricey venue for a fun, quirky evening with friends or business colleagues. When not wintering in India, flamboyant Howie may greet you, ushering your posse to La Salon Neige, where you’ll scoop courses from hospital bowls, ash trays and sensual models dressed in slices of Carpaccio, brandishing salad dressing in syringes and deep-fried cricket tidbits—crunchy croutons! Opt for the upper level lounge and you can watch from above as dykes, belly dancers and aerial artists perform. Don’t worry about crumbs in bed; get into the act while the drag queens vamp and the dancers swirl. Between courses, enjoy a Lavender Love or Leap of Faith cocktail in the Chapter 21 bar. Or venture to the downstairs smoking room that doubles as a gay toilet. While puffing on a joint, don’t be surprised if spontaneous music erupts or locals engage you in conversation. There are supperclubs in Istanbul, London, Los Angeles and San Francisco, but this is the original. And there’s nothing conventional about it!

Why we love it: A city slicker–approved beach retreat with a vibrant art collection

The Highlights:
- The secret indoor pool up a staircase from the main pool area
- Fresh-baked breads by pastry chef Simone Colla served daily in the Filosofía restaurant
- An entryway featuring a rare sculpture by KAWS and vintage armchairs hung like swings from the ceiling

The Review:
The people watching is just as entertaining as the artwork at Casa Malca, a mansion once maintained by Colombian drug lord Pablo Escobar but now owned by New York gallerist and art collector Leo Malca. Set on a Caribbean-facing swath of sand next to the Sian Ka’an Biosphere Reserve—and just a short bike ride from Tulum’s beachfront boutiques and restaurants—the hotel features 71 rooms, complete with polished concrete floors, floor-to-ceiling windows overlooking the ocean, and bold artwork from Malca’s personal collection. A black-and-white print inspired by Keith Haring covers the lobby bar, while antique baby dolls adorn the walls in one of the hotel’s three restaurants. The pool and beach areas are more sedate, with cerulean daybeds and colorful hammocks studded like jewels among the leafy palms.

Opened in early 2018, Harbor Club is a modern resort housed on Rodney Bay Marina on St. Lucia’s northwest coast. The overall feel is crisp and aquatic, with the bright-white building resembling a cruise ship on the harbor. Given the hotel’s marina setting, there is no direct beach access, but there is a sparking complex of swimming pools with mountain and water views. The hotel also provides complimentary shuttle service via a fast boat to the beach on Pigeon Island Nature Preserve, as well as towels and chairs for a day on the sand. Guest rooms are like spacious ship cabins, decorated in cool shades of blue with views of the marina or mountains. Eight swim-up rooms on the ground floor even feature private patios directly over the swimming pool area. The hotel’s half-dozen restaurants include Caribbean-Asian fusion spot 14North on the top floor, a modern sushi bar, and farm-to-table eatery Julia’s, and more options are available a short walk from the property. A full-service spa and fitness center, nightly live entertainment, and sunset cruises round out the amenities.

Blue Heaven is a favorite in Key West—Jimmy Buffett even mentioned it in one of his famous beach tunes. The whimsical courtyard is filled with brightly colored tables and chairs, twinkly lights, foliage, and stray animals. The bar and restaurant is owned and operated by a husband and wife whose creative backgrounds in art and literature inspired the space. There’s a mini art gallery, a sandwich shop, and roaming roosters on the grounds. Once a boxing ring (with Ernest Hemingway as referee), the spot now pays tribute to the Caribbean, with bright accents and Cajun seasonings on the menu. Menu highlights include the scallops, which are locally celebrated, served with white wine and lemon butter with tomatoes, onions, mushrooms, and lots of garlic. Locals say the Key lime pie is one of the best in town.

Why we love it: A peaceful eco-lodge on Dominica’s “wild” southeast coast

Highlights:
- A “barefoot luxury” vibe
- Proximity to the beach
- Villas surrounded by a working fruit plantation

The Review:
An agritourism pioneer, Citrus Creek blends hospitality with a tropical fruit plantation on Dominica’s rugged east coast. In building the resort, owner Hervé “RV” Nizard repurposed parts of his 20-acre farm in Taberi, adding a dozen self-catering cottages and villas. Ranging from one to three bedrooms, the accommodations include a safari tent and a stone tree house. Focused on nature, Citrus Creek trades TVs for rainforest hikes and a swimming pool for plunges in a pristine river. The property also lacks air-conditioning, but shade trees and prevailing winds keep it comfortable year-round and help maintain a “barefoot luxury” vibe.

Each room has a kitchen, stocked with breakfast goodies like tea, coffee, bread, butter, jam, and honey. For those who would rather dine out, a cafe offers half-board plans and operates every day from 10 a.m. to 5 p.m. (or later with reservations). Take your dinner on the veranda overlooking the river, choosing among French-Caribbean delicacies like onion pie, caramel pork, grilled lionfish, and smoked marlin quiche. Other on-site perks include a tour desk, car rentals, and, soon, a pier set within the jungle that will be equipped to welcome sailboats.