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  • 148 Calle San Sebastián, San Juan, 00901, Puerto Rico
    Feel instantly cool when you slip through the unmarked wooden doors and enter La Factoria. Garden lights hang from the graffiti-covered walls (designed to look artsy-shabby with a stylish restraint), seductive music plays, and the liquor bottles behind the bar are lit from beneath to add to the glow. The flattering amber light in this neighborhood bar invites whispered conversations and lingering glances. La Factoria, which introduced San Juan to the craft cocktail when it opened in 2013, encourages experimentation. Take your time enjoying your drink of choice, but be sure to wander a bit further into the sprawling building where you’ll come upon separate spaces with different moods: a wine bar, a speakeasy, a dance floor.
  • A few kilometers inland from Mykonos Town, Ano Mera is a small Cycladic idyll of a village. To get a feel for how people lived before the tourism boom, wander the streets and smell the scent of fresh baked bread. The Panagia Tourliani church and the Paleokastro Monastery are centuries old, and you can also find graves of the ancient Geometric era of Greece here.
  • 1201 Broadway
    The Art is a worthy base for those looking to explore the galleries of the Denver Art Museum, the Clyfford Still Museum, and the Kirkland Museum of Fine and Decorative Arts, which are all within a few minutes’ walking distance. In fact, the glass-walled property feels a bit like an exhibition space in its own right: Upon arrival, guests are greeted by Leo Villareal’s dazzling 22,000 LED–bulb installation above the entrance, while hundreds of other works by the likes of Frank Gehry appear throughout the public spaces—see them on a guided tour of the hotel’s art collection, offered on Saturdays. Minimal guest rooms have light wood furnishings, luxury linens, and neutral walls—the better to serve as a blank canvas for more original artwork—as well as windows overlooking the mountains or city lights. If you’ve worked up an appetite with all that cultural appreciation, order the signature burger with spicy mayo at FIRE restaurant, or sip a Matisse martini with Colorado-made vodka on the fire pit–warmed terrace.
  • 101 South Shore Road, Southampton SN 02, Bermuda
    Surrounded by swaying palms, tropical flowers, pink sand, and sapphire waters, the 100-acre Fairmont Southampton is Bermuda’s ultimate luxury destination. The 593 rooms and suites are among the largest on the island, and feature marble baths stocked with Le Labo products and private balconies that look out onto the Atlantic Ocean, Great Sound Harbour, or the lush landscaping of the on-site Turtle Hill Golf Club. A pool, beach club, dive center, kid’s camp, and tennis courts—plus that 18-hole championship course—offer plenty to keep guests busy. If you prefer to kick back, opt for a lavender-oil massage at Willow Stream Spa, a sprawling space complete with a well-stocked health club, sauna, and steam rooms, or grab a sundowner at one of the resort’s 10 restaurants, bars, and lounges.
  • 2411 Alaskan Way, Seattle, WA 98121, USA
    The Edgewater made its mark in Seattle history as the place The Beatles stayed when they came through on tour in 1964. Other rock stars (and those who like to travel like rock stars) have since stayed at the Edgewater, choosing it for its singular location on Pier 67 perched over the waters of Puget Sound. The public spaces make design references to the Pacific Northwest, with natural wood and stone everywhere. Waterfront rooms have sunset views that are nothing short of spectacular, and all the rooms are well-appointed, with gas fireplaces and spa-style bathrooms.
  • To get from point A to B on the river delta, you’ll need to board a water taxi. These polished wood boats cruise the canals day and night, dropping passengers off and picking them up at rental houses, cabin complexes and restaurants along the way. The ride, of course, is part of the fun. Board one at the harbor - and make sure you know where it’s going before you sit down, or it might be awhile before you find yourself back in civilization.
  • Little Cayman, Cayman Islands
    Despite its size (10 square miles) and population (fewer than 170 permanent residents), Little Cayman enjoys a worldwide reputation among serious divers. The island is renowned for its exceptional underwater visibility and vertigo-inducing walls, especially north-shore Bloody Bay. Dive boats flock to Three Fathom Wall, where bulbous coral heads teeming with fish rise to within 10 feet of the surface. Snorkelers are likely to encounter schools of blue tang and stoplight parrot fish, as well as hawksbill turtles and nurse sharks.
  • Woodstock, Cape Town, South Africa
    A colorful working-class neighborhood near downtown that had fallen on hard times, Woodstock has been revitalized with a mix of galleries, artists’ studios, boutiques, and restaurants. Much of the area’s original vibe remains, however, thanks to the long rows of colonnaded shops that edge Albert and Victoria roads. Among the nearby storefronts that are open throughout the week are Espresso Lab Microroasters and Luke Dale-Roberts’s award-winning restaurant, the Test Kitchen. Continuing down Albert Road, you’ll find spots like the Woodstock Co-op and the very trendy Woodstock Exchange, with a great array of places to eat and stores selling local goods. At the end of Albert Road, there’s a concentration of galleries, including the Stevenson, Goodman, and SMAC. On Saturdays, Woodstock draws crowds to the Neighbourgoods Market, a prepared foods extravaganza in the Old Biscuit Mill.
  • Capitol Driveway Northwest
    The U.S. Capitol Building is the epicenter of all D.C. political action—this is where the country’s most important battles are fought. Home to the House of Representatives and the Senate’s meeting chambers for more than two centuries, it’s also an art gallery in its own right, with priceless paintings and murals adorning the walls and ceilings. Take the free guided tour and marvel at the parade of political heroes and villains who have roamed its halls during pivotal moments in U.S. history. The Capitol is located within easy walking distance of the Library of Congress, the Supreme Court, and the U.S. Botanic Garden.
  • Dongzhimen, Dongcheng, Beijing, China
    When Beijing’s hutongs—narrow alleyways that connect to form mazelike neighborhoods—were originally built, they were lined with stone houses that had central courtyards. In 1949, with the founding of the People’s Republic of China, there were more than 3,000 hutongs; so many have been razed since that time that there are now fewer than 1,000. The remaining hutongs are where locals chat with their neighbors, sit outside on hot summer nights, buy fruit, and tend to their gardens, all without leaving their own alleyway. Seeing this side of traditional Beijing life is delightful and serves as a marked contrast to the many shops, restaurants, cafés, and bars that now occupy the courtyard homes lining the alleyways.
  • Bankside, London SE1 9TG, UK
    It’s impossible to ignore the hulking 1950s architecture of the Tate Modern, slap-bang in the middle of the most-walked part of the South Bank. A visionary refurb of this former power station has resulted in an artistic behemoth with multiple gallery spaces (containing both free exhibitions and ticketed exhibitions), including the fantastic Turbine Hall for oversize installations. Outside, the Millennium Bridge leads over the Thames to the City and the great domed St. Paul’s Cathedral.
  • 225 7th St SE, Washington, DC 20003, USA
    The Eastern Market, now a National Historic Landmark, opened in 1873 to serve the Capitol Hill neighborhood (an 1805 version, located down by the Navy Yard, was a casualty of the War of 1812). The brick market hall, packed with butchers, bakers, vegetable markets, cheese vendors, flower kiosks, and a lunch counter, is bright and charming. Under the shed roof outside, additional local produce is displayed and sold. On weekends, booths selling vintage goods and handmade jewelry, housewares, and clothing do a brisk business down the center of 7th Street. Crowds spill out of the cafés, taco joints, and bagel shops occupying the first floors of the row houses along the block, adding to the lively mix at the market.
  • Piazza San Marco, 328, 30124 Venezia VE, Italy
    The Basilica San Marco is Venice‘s crown jewel. Situated at the eastern end of Piazza San Marco, the cathedral was built around 1078 on the site of an earlier house of worship. It is famously the home of the remains of the apostle Mark, which were said to have been smuggled from the Holy Land by Crusaders in a barrel of pork. The basilica is not just a wonder from the outside; its glittering gold mosaics make it one of the most breathtaking examples of Byzantine design in the West.
  • Highway 1
    The island’s first settlement, Holetown, on the west coast, is a favorite destination of shoppers thanks to Chattel Village. Beautiful old fretwork houses painted in a rainbow of bright colors have been turned into a collection of shops. Visitors can browse for gifts and souvenirs as they wander the landscaped grounds before enjoying a meal or drink at one of two restaurants.

  • Norzagaray 204, San Juan, 00901, Puerto Rico
    Old San Juan is known for its atmospheric and historic hotels, but none quite match the Gallery Inn for personality and creativity. Composed of six intertwined town houses, this endlessly fascinating hotel beckons guests to wander through its nine interior gardens and patios, and seven parlors and porticos. Dating to the mid-1700s, the oldest building, La Cueva Del Indio, is located above Old San Juan’s north walls, meaning the views out to sea are the same ones that captivated the conquistadors.

    Owner Jan D’Esopo, is a well-known sculptor and her works dot the hotel’s meandering interior, which has enough comforts and homey character to avoid feeling like a museum. Equally unique are the 25 rooms, decorated with everything from silk screens and watercolors to sculptures and paintings. Some even feature elegant, four-poster beds and balconies with views of the ocean. Just don’t expect to watch TV—one, there are no TVs, and two, the views out over the old fortress walls are better than anything on Netflix.