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It’s hard to believe that this iconic property once consisted of just two 17th-century “caves” that had been used to store wine when it launched in 1985. Today, the family-owned hotel has 17 rooms spread out over five floors, all of them with terraces or balconies and jaw-dropping views of the caldera and brilliant blue Aegean. The rooms were completely refurbished in 2015—followed by the public areas and infinity pool in 2017—favoring clean, contemporary lines, white-washed walls, and luxury that envelops you without distracting from the stunning scenery; several rooms feature heated plunge pools, while one has a free-form “river pool” that runs through it. A poolside bar serves lunch and snacks, but you shouldn’t miss dinner at sister property Canavas Oia Suites, just a short walk away. For a truly unforgettable experience, you can even charter the hotel’s yacht for a sunset tour.

One of the newer boutique inns to emerge in the Catskills, this 11-room property is a gorgeous mix of old-fashioned elegance and urban styling. Guests can expect classic features such as stone fireplaces and sheepskin rugs along with a glorious hodgepodge of vintage sofas, Moroccan tiling, and framed butterflies. Rooms feature white walls and matching linens, with pops of color in the form of grass-green rugs, tufted velvet chairs, bright wallpaper, and serene, forest-inspired art prints. Just be aware that about half the rooms—specifically, those on the third floor of the old house—share common bathrooms. There’s also a cottage with three bedrooms and its own kitchen, where guests can bring their pets provided they let the owners know ahead of time. Don’t miss the Sunday brunch served in the intimate Bar Room—one of the inn’s owners is a chef by profession, and his culinary artistry gets consistently rave reviews.

Continue west beyond Boulder’s iconic Pearl Street walking mall, and you’ll find yourself surrounded by incredible restaurants. New to the block is Bartaco, a fun, hip South American–inspired eatery that always seems to be hopping; while there might be a wait for a table, keep an eye on the first-come, first-served bar seating. Choose from unique taco flavors like glazed pork belly with arbol chili sauce or tamarind-glazed duck, and sides like a spicy cucumber salad or fresh pineapple with lime—and make sure to save room for the fresh, hot churros. The Kitchen, self-described as an American bistro, is one of the fancier, albeit relaxed, eateries, offering brunch, lunch, and dinner that have been sourced as much as possible from local farmers. For delicious pub food, jump into the classic West End Tavern. Burgers, beers, ribs, BBQ, and more make this a place to satisfy everybody.

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.

Located at the Casa del Mar Beach Resort, this casual, indoor-outdoor restaurant starts serving breakfast at 7:30 a.m. and stays open until 10 p.m. Whether you visit morning, noon, or night, you can look forward to everything from local fish to oversize salads and hearty sandwiches. Cocktails are another specialty—in fact, the restaurant hosts happy hour three times a day with two-for-one drink offers. Other nightly specials popular with both visitors and locals include all-you-can-eat ribs on Tuesdays and karaoke on Wednesdays, made all the more fun by the breezy location and ocean views. Die-hard sports fans don’t even have to miss the game, since the restaurant tunes its TVs to whatever patrons request.

Named for the Japanese word for enlightenment, this boutique property marries classic Cycladic architecture (cube-shaped structures, whitewashed stone walls, arched entryways) with the clean lines of locally made furnishings in naked wood. None of the 25 rooms and 10 suites are the same, but most have private outdoor whirlpools or plunge pools, plus plush beds that make it impossible to leave. Nearly all of the public spaces, however, offer stunning views over Mykonos (about 1.5 miles away) and the bay, and make striking use of night-lighting, especially at the pool, which is built into the natural rock face. A grottolike spa features two treatment rooms, a futuristic-looking whirlpool area, and a hammam for stylish pampering sessions. The hotel offers complimentary transportation to Mykonos, but with its inviting Bar & Sunset Lounge and a restaurant that is garnering awards and accolades, you may decide to stay put for the duration of your vacation.

Built in 1907 by the same architect who designed the National Theatre and Hallgrímskirkja church, Apotek is full of historical resonance. The Art Nouveau–style building was once the country’s largest edifice and served as the city’s primary pharmacy from 1930 to 1999, a distinction that gave the hotel its name when it opened in 2014. The property’s 45 rooms blend elements of the past while seamlessly incorporating modern design touches, employing neutral colors, parquet floors, and simple-but-refined furnishings to create a sense of calm; subway-tiled bathrooms with walk-in showers have a bright, clean look. You don’t have to wander far to enjoy one of the busiest watering holes in Reykjavik: Apotek Kitchen + Bar is a hot spot for artisan beverages, where cocktail “pharmacists” craft potions for every ailment. Bonus: Not only does it overlook the Austurvöllur park, it’s just around the corner from the Icelandic Punk Museum.

Right in the center of town, Capri Tiberio Palace mixes la dolce vita glamour with a globe-trotting sensibility that’s equal parts quirky and elegant. Wanderlust-inducing knickknacks such as globes, vintage trunks, and an eclectic collection of art stud the public spaces, and bookshelves are stocked with coffee-table tomes from the publisher Taschen. A white baby grand provides the soundtrack for aperitivo hour at the Jacky Bar, where wicker poufs, striped blue-and-white banquettes, and Panama hats repurposed as wall decor signal vacation vibes; things are slightly more reserved at the terrace restaurant, a formal space whose brightly colored dishes (think seared scallops with almond sauce and beef tartare with chestnut cream as well as kosher fare) are rivaled only by the panoramic views of the island’s craggy peaks coast and azure sea. And the indoor-outdoor swimming pool, though small, is a savior in the summer heat.

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.

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.

Anchoring a $1.2 billion mixed-use development, the 23-story Palace Hotel sits opposite the ancient Otemon Gate of Edo Castle and was designed to juxtapose tranquil green space and vibrant concrete jungle, with all guestrooms featuring views of the Imperial Palace’s gardens and moats; most have open-style bathrooms, while more than half feature terraces and balconies, a rarity in Tokyo. Natural motifs—from the leaf-shaped counter and shadowy outlines of trees on the walls of Bar Lounge Privé to the hand-tufted, mossy-hued carpets in the lobby—reinforce the link to the outdoors. The hotel’s artwork brings to light the work of Japanese contemporary artists, with about 1,000 paintings and watercolor, glass, metal, and other pieces on display.

Starwood’s W Hotel chain is known for its contemporary style and design, and the W Seoul-Walkerhill is no exception. Set against the picturesque backdrop of Mt. Achasan—a popular hiking destination in the area—and overlooking the Han River, the hotel is located in a peaceful location rather than amid the chaos of downtown Seoul. Opened in 2004, the W Seoul-Walkerhill has earned a reputation among trendsetting locals for hosting some of the city’s best events. Fashion shows, DJ parties, and design fairs are just a smattering of the happenings you can expect to experience during your stay. The hotel’s futuristic Woo Bar has been featured on countless Korean television dramas, and it’s a popular place for young celebrities to see and be seen. Got a smartphone? Use it to check in upon arrival, and throughout your stay as your room key.

No, your mastery of languages hasn’t led you astray—“amigo” isn’t a French or Flemish word. Rather, when the Spanish controlled the city in the 16^th century, they misunderstood the Flemish word for “prison,” and so the city jail earned its incongruously friendly nickname. Now one of Brussels’ premier luxury hotels, under the discerning eye of hotelier Sir Rocco Forte, the landmark has finally earned its name, welcoming celebrities, captains of industry, and international dignitaries into its refined space. Designed by Forte’s sister and longtime collaborator, Olga Polizzi, the hotel blends contemporary Italian and Belgian styles—clean-lined furnishings, velvets and Belgian linens in muted tones, soaring windows framed by heavy drapes—with distinctive Flemish classics like Magritte paintings and original flagstone floors. As impressive as it all is, especially when paired with its acclaimed fine-dining restaurant and popular bar, the real star is the view, which, from most rooms, includes the city’s famous town hall.

Though it lacks a beach, this family-owned and professional diver–managed resort on the rocky coast just south of George Town has direct ladder access into the Caribbean. Grand Cayman’s two famous underwater sites, Eden’s Rock and Devil’s Grotto, are just a short swim away, and boat trips offer the option of two daily dives (including night dives). Images by some of the world’s most respected underwater photographers decorate many of the tiled and comfortable smoke-free rooms, some of which have kitchens and private balconies or terraces. The vibe is laid-back; post dive, guests sit by the pool or swap stories at the palapa bar, which has the island’s best sunset vista. Managers Anne Briggs and Lisa Evans, the granddaughters of Sunset House’s founders, make sure everything runs smoothly and ensure visitors explore the best of Grand Cayman both on shore and underwater.

There’s a touch of Old World glamour to the Cape Royale—the imposing facade, the dramatic lobby, the bellmen in top hats—but just when you start to wonder if the whole experience is going to be resolutely old-school, you’ll find yourself pleasantly surprised by the sleek rooms. They feature contemporary furniture, granite and porcelain bathrooms, and a soothing palette of mostly grays and whites with the occasional punch of lime green or aqua blue. It’s also the site of six restaurants, cafes, and bars, each with its own theme, from Italian cuisine to healthy eating to Thai or Middle Eastern fare.

The city’s best beaches and nightlife—not to mention Green Point’s dazzling Cape Town Stadium, erected for the 2010 World Cup and now the site of many a mega-concert and local soccer match—are minutes away.