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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.

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.

Gothic and grand, this 18th-century former nobleman’s home stands proudly on the banks of the Grand Canal in the San Marco district. Venetian-born owner and interior designer (among her many talents) Francesca Possati has restored this historic home to its regal glory. She has worked with local artists to breathe new life into original woodwork, ornate trompe l’oeil ceilings, and silk wall hangings, resulting in a once-again polished and posh palazzo. The distinctly Venetian rooms—many with canal views—are styled with rich fabrics, bold wall coverings, and pristine period antiques and illuminated by Murano glass chandeliers. Of course, they’ve been updated with the latest modern perks (like Italian marble and whirlpool tubs in the bathroom).

Stroll the art-filled hallways, splurge for a tasting menu at the elegant restaurant, and watch the gondolas float by from the red-awninged terrace. La dolce vita, indeed.

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.

Romance is easy to come by at Emelisse, on a private beach on Kefalonia. One turquoise infinity pool spills into another before seeming to pour directly into the glittering Ionian Sea. Come evening, dozens of glowing lanterns illuminate the stone terraces and two outdoor restaurants, as well as the open-air cinema. Framed by dark cypress and cedar trees, the suites, villas, and two-story maisonettes cater to every combination of adults and children with teak canopy beds and fine Italian linens. Just as enchanting as the setting are Emelisse’s myriad activities. Guests can sign up for scuba lessons and tennis matches, or take a 25-minute walk to the quaint port town of Fiskardo. If you’re looking for more adventurous pursuits, the largest of the Ionian islands offers everything from steep cliffs and mountains (Mount Aenos is the third highest in Greece) to stunning sand and pebble shorelines.

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.

Hotel Solamar is all about providing warm SoCal hospitality. Mingle in the lobby during the daily happy hour, and rent a free designer bike for beachside cruising. You can even turn your room into your ideal retreat, thanks to an eight-option pillow “menu” and in-room spa services. Wellness-minded travelers should take advantage of the available yoga mats and tune into yoga, Pilates, and core-strengthening exercise programs on TV. Pets are also given special attention with free amenities that include welcome treats and beds.

The chic downtown hotel is design-focused without being stuffy, creating a laid-back vibe throughout the property. Oversized chairs, sleek mahogany furniture, and plush stitched walls adorn the rooms. Sunny days aren’t hard to come by in San Diego, so don’t miss the fourth-floor terrace with its memorable skyline views. You can also take a dip in the heated Shore Pool or catch some rays on one of the lounge chairs.

The most exclusive lodge in New Zealand, having hosted everyone from Queen Elizabeth II to the late Robin Williams, Huka Lodge feels like a refined country getaway set on the banks of the Waikato River near the North Island resort town of Taupo. Founded in 1924 by a charismatic Irishman named Alan Pye, the property was later reimagined by entrepreneur Alex van Heeren with the help of interiors specialist Virginia Fisher and famed New Zealand landscape designer Suzanne Turley. The surrounding grounds are ranked as a ‘Garden of National Significance’ by the New Zealand Gardens Trust. Whether staying in the lodge suites—which feature French doors that open up to a wooden terrace just steps from the river—or the lofty private cottages, guests will feel like royalty here.

Built as an aristocratic country manor in 1746, Kokkedal Castle was a private residence for much of its existence, hosting salons and parties for Copenhagen’s elite. Restored and opened as a hotel in 2011, the castle is now one of Denmark’s most luxurious stays, set on acres of sprawling parkland along the Danish coast, just 30 minutes north of Copenhagen. With its manicured gardens, afternoon tea on the terrace, and 18th-century–inspired decor, it feels like that friend’s country estate you’ve just been waiting for an invitation to—if, that is, your friend has an excellent restaurant in the original cellars, specializing in Danish and French country cuisine, and a world-class holistic spa ready to cater to your every whim.

To top it all off, thanks to the castle’s location, both Copenhagen and the region’s myriad other sights are within an hour or two’s reach, either by train or by car.

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.

Even during Antigua Sailing Week, when English Harbour is chock-a-block with yachts from all over the world, the 28-room Inn at English Harbour remains serenely detached from the chaos. The inn is five minutes by water taxi from the center of things at historic Nelson’s Dockyard, but its tucked-away location on a white-sand beach backed by 19 leafy acres (and a no-kids-under-10 policy) ensures tranquility. Four snug rooms, with marble floors and queen beds, occupy two beachside cabanas, while 25 more generously proportioned suites, all with dark mahogany floors, four-poster king-size canopy beds, and verandas or balconies, are in three wooden buildings sitting farther back among the tropical greenery. Although the Terrace Restaurant and Stone Bar are in the property’s original stone house, the rooms, despite their colonial look, are relatively modern, which means there is a flat-screen TV, an iPod docking station, and Internet access.

The Aubrey sits at the edge of Barrio Bellavista, a few steps from Santiago’s bottle-green 1925 funicular (which takes visitors up to Cerro San Cristóbal) and just below the zoo (sometimes guests can hear the animals when they’re lying by the pool). Open since 2010, this 15-bedroom boutique hotel is housed between two 1920s mansions built by the same architect. The larger of the two houses once belonged to famed Chilean railway magnate Domingo Durán. Today, the hotel is owned by a Brit and an Aussie who spent $3 million and several years transforming it into its current state.

The bedrooms are split between the two mansions, and there’s also an outside block housing a few pool suites. A cobbled terrace runs between the restaurant and piano bar. The interiors are inspired by the early 20th-century art deco movement and feature statement art deco furniture, printed fabrics, and elaborate wallpaper.

This top-of-the-line property of the San Vicente Hotel Group (which owns the nearby San Vicente and Hostal Villamil), is a three-level, all-white hotel that feels almost like a beach villa. It’s actually just a couple of blocks from Puerto Villamil’s two-mile-long stretch of municipal sand, and most of the surrounding sandy streets are filled with palm trees. The facilities here provide enough so that guests’ only real concern will be getting to other parts of the island. The restaurant stays open all day with a varied menu and drinks list. There are flat-screen TVs in the rooms and free Wi-Fi in common areas. Shaded by a few umbrellas and a cane canopy over the Jacuzzi, the rooftop terrace is the favorite hangout for most guests at this small hotel. In every direction comes another jaw-dropping view, such as the Pacific Ocean, the Sierra Negra Volcano, the highlands, or a saltwater lagoon filled with flamingos.

Located just outside of Santa Cruz in the heart of the Colchagua Valley, Clos Apalta Residence (formerly Lapostolle Residence) is known for its premium Chilean wine. In 2005, the Marnier family opened the stunning property on a steep hillside in the micro region of Apalta. In addition to a state-of-the-art, gravity-fed winery, they built four villas, giving wine lovers a unique place to stay. Today, Clos Apalta functions as a Relais & Chateaux luxury hotel, complete with beautiful views of the valley and its surrounding mountains. Guests can relax on their private terrace, in the lodge, or by the infinity pool, sipping house wines while enjoying the vistas. They also have exclusive access to the dining room, where chefs use produce from the hotel’s own organic garden, and tours of the owners’ wine cellar during visits to the winery.