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Located on Fleming Street in the heart of Old Town Key West, the Marquesa has everything you might expect from a romantic coastal-Florida retreat. Wide porches overlook lush gardens and a bijou pool at the center of the complex, and brick paths shaded by large palms and tropical foliage give the 1884 Greek Revival–style property a secret hideaway feel. It’s understandable if you want to hole up in the guest rooms, which reside in traditional clapboard conch houses and are furnished with an eclectic collection of wood pieces sourced from around the world. In 2018, Marquesa 4-1-4 opened across the street, featuring a new compound of three buildings around a central swimming pool and courtyard. After a day spent exploring nearby Duval Street, make your way back to Café Marquesa, which is perennially packed with locals and visitors enjoying fresh seafood and an inventive menu.

Continental’s downstairs bar—with a marble countertop and chilies, garlic, and aged ham hanging overhead—transports diners to Spain or Portugal. Despite the old-world ambience, however, the menu and staff are young and playful. Pop in for a meatball sub and vermouth at lunch, or enjoy king-crab-stuffed zucchini flowers before moving on to slow-roasted lamb in the upstairs bistro. In either case, complement your meal with something canned—the deli’s specialty— whether it’s the seafood plate of the day or a “Cosmopoli-tin” cocktail. A whole wall of canned and jarred concoctions are also available to take home. In 2018, a second, and larger, outpost of Continental Deli was opened in the CBD.

The Wauwinet makes the most of its coastal setting between the Atlantic Ocean and Nantucket Bay. Next to the Coskata-Coatue Wildlife Refuge, the resort has 32 rooms, plus four cottages with separate living rooms and the three-bedroom Anchorage House across from the main inn. In addition to private beach access and bikes to explore the island, guests can take out a kayak, play a game of tennis, or watch a movie in their room with hot buttered popcorn. A spa offers sea-inspired facials, massages, and body treatments. TOPPER’S restaurant is known for its Retsyo oysters, harvested only 300 yards from the restaurant, and offers transfers to and from White Elephant Hotel’s Brant Point Grill on its 21-passenger boat, Lady Wauwinet. The inn also provides regular shuttle services to the ferry and Nantucket town (about 10 miles away), and outside of peak summer season will drive guests to the village of ‘Sconset in its 1947 Woody station wagon.

Upon your arrival at this 556-room resort, you might be disappointed to find a small pool instead of sandy palapas overlooking the sea. But the Renaissance makes up for its location on a busy thoroughfare in the capital city of Oranjestad with its own private island, a 40-acre oasis dotted with pink flamingos and iguanas. After an eight-minute water-taxi ride, you can choose between two distinct beaches—one adults-only, the other designated for families—plus an array of vacation-friendly amenities. A beachside bar and grill serves up burgers and wood-fired pizzas; an open-air spa offers Swedish and cold stone massages, as well as reflexology; and an extensive water-sports program includes activities like snorkeling, scuba diving, and ocean kayaking. If that’s not enough to tire you out for the evening, a steak house and casino await back at the main resort.

Set on St. Lucia’s westerly Anse Cochon beach, Ti Kaye is a secluded, adults-only oasis that feels worlds away from the rest of the island. Each of the 33 cliffside, gingerbread-style houses feature outdoor showers and verandas with double-wide hammocks, and some even include plunge pools. Since there are no TVs, the focus remains squarely on the picturesque beach, home to a PADI diving center, crashing waves, and breathtaking sunsets. The same is true in the resort’s two open-air restaurants (don’t miss the banana pancakes at the beachfront grill) and treetop spa. Rum connoisseurs can schedule a tasting in Ti Kaye’s wine cave, but if you crave a rowdier scene after all the relaxation, know that it’s a 20-minute drive to the nearest fishing village—you’ll want to make the trek on Friday nights though, when Anse La Raye hosts its weekly street parties.

Accessible only by seaplane, Kuredu rewards the adventurous with a secluded stretch of powdery white sand on the Lhaviyani Atoll. The resort is popular with dive enthusiasts thanks to its PADI certification center, but water babies of all stripes will find plenty to love, including snorkeling, catamaran sailing, kiteboarding, and private dolphin-watching trips. Those who would rather stay dry might prefer to hit the links: the country’s first golf course is right next door. A range of simple yet comfortable villas and overwater bungalows, many with private pools or Jacuzzis, provide a low-key crash pad after days spent among the waves; couples seeking even more quiet stay in the adults-only section of the property. Housed in a cylindrical domed aquarium on nearby Hurawalhi Island, the much-photographed 5.8 Undersea Restaurant is open for lunch and dinner, giving guests yet another opportunity to get close to their aquatic neighbors.

Housed on the Grand Cul de Sac, Le Barthélemy specializes in tranquility. All of the 46 rooms and suites have drop-down screens that transform outdoor terraces into private spaces. French chef Guy Martin, of the two-Michelin-star Le Grand Véfour in Paris, developed the menus for the two restaurants. Book the “Picnic Chic” service and a concierge will pack beach chairs, a hamper of canapés, and a bottle of rosé for you to take to any of the island’s secluded beaches.

Following renovations made necessary by Hurricane Irma, the hotel re-opened in October 2018 with an enhanced focus on wellness. In addition to new beachfront villas and three-bedroom suites, the property now features a hydrotherapy area, a traditional hamman, beach yoga, and an advanced fitness center with state-of-the-art equipment. There’s also a new beach grill serving light fare and a rooftop bar with DJs and live music.

The phrase “Dedicated to Art” is engraved in stone over the entrance of the Renwick Gallery, a reminder of its rich history as the nation’s first building created expressly as an art museum. More than a century and a massive renovation later, this mission continues to hold true. The Renwick celebrates contemporary craft and decorative arts through immersive installations, special exhibitions, and impressive collections of jewelry, wood art, and studio furniture. The curated works are both elegant and innovative, much like the Second Empire architecture of the building when it was first designed by Renwick in 1859. As with all Smithsonian Institution museums, admission is free.

Arriving at Viceroy Los Cabos (formerly Mar Adentro) is like getting a glimpse into the future of hospitality. Linked by a seemingly boundless plane of water, a series of minimalist white cubes—housing a rooftop bar, spa, world-class fitness center, movie theater, and more—rises from the desert landscape like a mirage, the work of Mexican architect Miguel Angel Aragonés. The view is memorable at Nido, a ceviche restaurant that sits under a nestlike dome of twigs. Equally striking are the 104 modernist guest rooms. Unlike the region’s traditional stucco and terra-cotta haciendas, they’re serenely spare, with floor-to-ceiling windows overlooking the Sea of Cortez and tablets that guests can use to create their own lighting concept.

To dress like the gondoliers you’ll need to pick up a pair of genuine friulane slippers at Gianni Dittura, one of the few remaining purveyors of the original footwear in Venice. Friulanes (or furlanes) were born of frugality in the 19th century, when the women of poor families in the Friuli countryside began hand-stitching cast-off fabric scraps to old bicycle tires to make shoes for their families. The slippers eventually made their way to Venice, where gondoliers snapped them up because they were cheap, comfortable, and didn’t scratch the paint on their boats. But as the years passed, friulanes inevitably went from lowly upcycled footwear to cult object and luxury product coveted by tourists. Today Gianni Dittura has two Venice shops, and you’ll find every color and size of the original velvet and rubber shoes, as well as more chic and contemporary winter models by in-house designer Laura Biagiotti.

The doorway of the Portrait Roma is one of a growing number of blink-and-you-miss-it boutique hotel entrances behind which contemporary luxuries await. Tucked behind an unassuming facade on a side street off the busy Via dei Condotti, the Portrait Roma is part of the Lungarno Collection, a small group of boutique hotels owned by the Ferragamo fashion house. Opened in 2006, the property prides itself on customized service, and each of the rooms comes with a Lifestyle Manager, or 24-hour concierge, who provides personalized holiday management throughout the stay based partly on the guest questionnaire completed before arrival.

All 14 rooms are suites, and each is classically decorated and designed to mirror the prestige of the Ferragamo brand. Rooms are accented with linen, leather, and cashmere, as well as artwork that evokes the beauty and spirit of Ferragamo. Weather permitting, the rooftop terrace hosts food and drink service and offers views of the historic center.

Opened in 1890 as an unofficial state guesthouse, the country’s first Western-style property built for the aristocracy to welcome an increasing number of foreigners, the Imperial Hotel has had a momentous history. Ravaged by a fire in 1922, it was rebuilt in 1923 by Frank Lloyd Wright in Maya-Revival style, though it fell into disrepair over the decades and was demolished in 1967. The blocky current version comprises a main building and a tower that together house 931 rooms, but the interiors stick to the property’s past with leather headboards and velvet-covered furnishings. The hotel boasts the largest executive center in Japan, but more leisurely activities await in the 20th-floor swimming pool and sauna, in the fully equipped music room (complete with Steinway piano), and in 11 restaurants that range from upscale French and traditional Japanese cuisines to snack-worthy sushi and confections.

If you’re looking for a chic lodging with personality to spare, Park Hotel is it. Designed under the concept of ART—atrium, restaurant, travel—it occupies 10 levels of the triangular Shiodome Media Tower and pays homage to Japan’s natural beauty with a glass-enclosed courtyard (purported to be the largest hotel atrium in Tokyo) and trees and greenery dotting the spaces between the building’s 25th and 34th floors. An artist-in-residence program ensures that every room on the 31^st floor features unique murals and paintings by local creatives, while more conventional rooms come in light, neutral tones, but all are furnished with stylish pieces by B&B Italia. The hotel also houses a wood-paneled spa, an art gallery, and a kaiseki-style Japanese restaurant and casual French bistro where the dishes are pieces of art in and of themselves.

The creative energy of the Garment District in Midtown Manhattan has long been behind closed doors, but Archer Hotel, opened in early 2014, puts that artistic spirit on appealing display. A mix of fabrics, graphic prints, exposed brick, and floor-to-ceiling windows (with dramatic skyline views) pays homage to a neighborhood known for pushing the boundaries of fashion. Beyond its quirky style—including a house art collection with pieces spanning several mediums—this property entices with its rooftop bar, Spyglass, perched on the 22^nd floor with views of the Empire State Building and the Chrysler Building. Archer excels at the small stuff, from in-room Nespresso machines and free Wi-Fi to gorgeous black-and-white subway tiled bathrooms with luxurious walk-in showers. Unwind after your day with an aperitif at the Foyer Bar, complete with seasonal outdoor patio.

Housed in side-by-side 19th-century townhouses amid the gas streetlights and cobblestoned streets of Boston‘s Beacon Hill, the high-end Beacon Hill Hotel retains a distinctly European feel. The original owners and neighborhood residents Peter and Cecilia Rait bought the properties with the intent of opening a hotel and bistro. Nowadays, the property is managed by Saunders Hotel Group, but the who’s-who clientele hasn’t changed. Since the hotel opened in 2000, the intimate property has hosted innumerable A-listers seeking a lower profile, including Todd English.

Each of the 13 rooms has plantation shutters, pedestal sinks, flat-panel TVs with DirecTV, and windows that actually open for fresh air. The second-floor common area invites guests to meet and mingle. Plus, the hotel has a private, residential-feeling roof terrace overlooking Charles Street, perfect for morning coffee or afternoon reading.