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  • 5009 NE 11th Ave, Portland, OR 97211, USA
    Situated on Northeast Portland’s Alberta Street, smack in the middle of the Alberta Arts District, Caravan is an unique alternative to the same old hotels or vacation rentals. The hotel is comprised of six tiny, individually styled houses for rent, from the cabin-like Skyline (made mostly from upcycled material) to the Amazing Mysterium (a vaguely steampunk affair modeled after a vardo gypsy wagon, with lovely additions such as stained-glass windows and lots of built-in shelving). In true Portland style, the houses are clustered together in a “pod,” similar to how many of the city’s famous food carts are arranged. In lieu of a lobby, there’s a central outdoor common area with a fire pit (s’more-making is encouraged, and supplies are provided). Note that live bands perform for guests and a limited number of community members on Wednesday evenings during the summer months, and the whole area gets busy on the first Thursday of every month, when Alberta Street transforms into a pedestrian-only night market-cum-street party that lasts well into the evening.
  • 24 Wharf St, Wellington, ON K0K 3L0, Canada
    Ontario has another wine destination, Prince Edward County, affectionately named “The County.” This cluster of towns, about 2.5 hours east of Toronto, is home to some of Ontario’s best wineries. But never was there a great place to stay until summer 2015 when Jeff Stober, the hotelier behind Toronto’s stylish Drake Hotel, opened a rural clone, the Drake Devonshire. It’s the ideal retreat for travelers wanting their Drake by Lake Ontario. Once a 19th-century foundry, the building is now a contemporary farmhouse-cottage, decked out with 11 individually-designed hotel rooms and two suites in the quaint town of Wellington. The property offers coziness all year round in the communal living room and out back over a lakeside fire pit and s’mores. Guests can hang in the barnlike Pavilion for musical performances, sommelier seminars, seasonal events, or just to gawk at the floor-to-ceiling mural by Brooklyn artist FAILE. It doesn’t hurt that Sandbanks Provincial Park—known for its 60-foot sand dunes—is practically the backyard of the Drake Dev.
  • Frigate Bay, St Kitts & Nevis
    A collection of rambling beach bars, The Strip on South Frigate Bay is the best “lime” on St. Kitts—a beach bash by day that transitions to an open-air dance party, moveable feast, and pub crawl by night. The area is within walking distance of the St. Kitts Marriott Resort, but it’s a popular nightlife destination for locals and visitors from all over the island. Don’t miss Mr. X’s Shiggidy Shack, the most famous bar on St. Kitts, where you can enjoy grilled lobster alongside an ever-changing lineup of live entertainment, from karaoke to fire-eaters. Also worth visiting are Vibes (St. Kitts’ closest thing to a sports bar), ChinChillas (for Mexican food), and The Dock Bar, which offers a more relaxed scene and, as its name suggests, its very own dock. Wherever you land, expect live bands and DJs to keep the dance floor hopping well into the wee hours. If you get tired, cool off and then rev up with a “Ting with a Sting,” a popular drink of local CSR rum mixed with grapefruit soda.
  • 600 F St, San Diego, CA 92101, USA
    At first glance, the lobby is the place to be at this boutique hotel in the Gaslamp Quarter. At check-in guests are offered a selection of local wine and beer—and again during happy hour. Under soaring ceilings supported by leather-wrapped pillars and surrounded by colorful art, you can sip and socialize. But don’t ignore the scene on the roof, either, where you’ll find a pool with oversized, floating pillows; fire pits with food and drink service; and views of the Coronado Bridge, Mount San Miguel, and the old and new architectural icons of downtown. In fact, the rooftop is so special, you may want to book the only accommodation in the 159-room hotel that grants you direct access to it: the Cabana Suite, where a private staircase leads to your own poolside cabana. On the other hand, if you’re traveling as a family, you may find that another option beats private rooftop access: the Star Suite, complete with three king-size beds, two of which form a custom-built bunk bed. Either way, expect ultra-modern furnishings paired with skyline views.
  • Ballyfin, Co. Laois
    For people who lament that they weren’t born into Downton Abbey–style gentility, Ballyfin, which opened in 2010 after nearly a decade-long restoration, is a fast track to 1820s-era refinement from the moment guests pull up to the front drive. A team of butlers and maids line up on the stone estate’s front steps to unload bags and whisk visitors into the lobby, and from there the Ballyfin experience is a dreamy blur: drinking tea out of antique china while wrapped in an Irish-wool blanket by the fire; being lulled to sleep during a massage in the basement spa; soaking in a clawfoot tub and surveying the meticulously sourced antiques in one of 15 rooms.

    Guests are basically lords or ladies for a night or two at this neoclassical home an hour west of Dublin in the county of Laois (pronounced “Leash”). For those who bore of pure leisure, there’s a stone tower to climb, horses to ride, 600 acres to explore, and a lake to walk laps around or row through. The pricey room rates can (almost) be rationalized by the inclusive evening champagne receptions, fancy three-course dinners, snacks, picnic lunches, and Irish breakfasts.
  • 78 Queen St, Charleston, SC 29401, USA
    The salmon-colored stucco buildings comprising the Elliott House Inn have a long history that runs parallel with the city’s. Built in the aftermath of a citywide fire, the property’s main structure was then shaken in an 1886 earthquake (the characteristic Charleston earthquake bolts are visible on the building’s facade) and battered by 1989’s Hurricane Hugo. The bed-and-breakfast reopened in 2011 after two years of renovation and redecoration, reinventing itself yet again. The main building is a classic Charleston single house, built with its narrow end on the street and a long piazza running along its length.

    The rooms, with their botanical prints, hardwood floors, and Oriental rugs, are traditional in a way that’s elegant and charming rather than fussy. Rooms are available both in the main house and the single-story building across. The quiet courtyard provides an oasis from the city streets with its wisteria-dotted pergola and light-draped palmetto trees.
  • Via Romana, 17, 50125 Firenze FI, Italy
    La Specola, one of the oldest science museums in Europe, contains a collection of specimens of the natural world—some of which date back to the 16th century. It includes strange and wonderful objects ranging from tiny iridescent green beetles and multicolored butterflies to whale and rhinoceros skeletons. There’s even a hippo, preserved by taxidermy, that was once pet to the Medici family and lived in the Boboli Gardens! The extraordinary, if slightly creepy, anatomical waxes filling the last four rooms of the museum were once used to train Florentine medical students. The frescoes and elaborate pietra dura inlays that decorate the walls and ceilings detail Italian scientific achievements.
  • Vicolo dell'Oro, 5, 50123 Firenze FI, Italy
    A hotel with the words “gallery” and “art” in its name would be remiss not to include at least a nod to the art world in its decor (though more than a few establishments have been known to throw up a wall-sized painting by a well-known artist and declare themselves art hotels). As Florence’s pioneering design hotel, the Gallery Hotel Art doesn’t skimp. Virtually the entire ground floor, from the lobby through to the lounge and trendy Japanese-Mediterranean-Peruvian fusion restaurant, is one giant gallery, its sleek white decor acting as the calming, understated counterpart to the contemporary art and photography not often found in this city.

    Indeed, don’t underestimate the groundbreaking nature of this hotel. Design hotels may be a dime a dozen these days, but when the Ferragamo family’s Lungarno hotel collection launched with this modern getaway designed by Michele Bönan, its clean-lined furnishings and chrome, white, and natural wood hues were a challenge to a city outfitted in rich brocades and dark wood antiques. As such, the Gallery Hotel Art isn’t the flashiest stay, but it is the kind of place you can relax and unwind and feel like you aren’t living in the Renaissance days.
  • Via della Scala, 18, 50123 Firenze FI, Italy
    Hundreds of years ago, at the height of Florence’s Renaissance heyday, visitors to this cultural capital wouldn’t have stayed in the kinds of luxury hotels that now line its picturesque streets. Rather, the well-heeled would have come at the behest of friends, lodging in private homes whose unassuming facades in the best neighborhoods belied their sumptuous interiors and private gardens, outfitted with art and artifacts collected from around the world.

    A guesthouse to its core, Casa Howard continues this Florentine tradition; there is neither lobby nor restaurant, and the owner Massimiliano Leonardi di Casalino lives in his own apartment here while in town (note, it can be rented when he’s away). Jennifer Howard Forneris, one of the design-conscious proprietors who has since passed away, was the daughter of renowned textile designer Luciano Forneris. She gave each room its own look, with finds from her and Leonardi di Casalino’s world travels. A media room is the sole common area, and a hammam steam room and an on-site concierge service are the only nods toward traditional hotel services. Insider recommendations are personalized according to guests’ preferences, and the honor bar feels more like a friend’s (well-stocked) fridge.
  • Piazza di Santa Croce, 50122 Firenze FI, Italy
    Standing in the Piazza Santa Croce, a statue of Dante looms over the square from the corner. Florence, where Durante degli Alighieri’s journey through hell, purgatory, and paradise was to begin but not end. In 1829 a tomb was built for him in the Basilica of Santa Croce—the largest Franciscan church in the world. The tomb has remained empty ever since as Dante’s body lies in Ravenna.
  • 100 Pointhouse Rd, Glasgow G3 8RS, UK
    Looking like the graph of a boom-and-bust financial market, the Riverside Museum’s jagged tooth–like facade, designed by the late Iraqi-British “starchitect” Zaha Hadid, is an iconic bit of development on the banks of the River Clyde. Inside, you’ll find Glasgow’s extensive collection of all things related to transportation, from skateboards and locomotives to prams, cars, and an Imperial Stormtrooper. Wander through the interactive displays to visit city shops, bars, and subway stops, then climb aboard a train, tram, or bus and get a feel for old public transportation. Visitors can also discover Glasgow’s rich shipbuilding history, explore the car and motorbike walls, and help put out a blaze with an interactive fire engine. Before leaving, head outdoors to the quayside to see the Tall Ship Glenlee—one of only five Clyde-built sailing ships that’s still afloat.
  • Piazza di Santa Trinita, 5R, 50123 Firenze FI, Italy
    What began in pre-war Italy as two small workshops in the Palazzo Spini Feroni on Via Tornabuoni has grown into a fashion empire and a brand synonymous with Hollywood glamour. A museum dedicated to the craftsmanship of Salvatore Ferragamo opened in this grand palazzo in 1995. The collection includes the wooden lasts, or forms, that Ferragamo used to shape shoes for stars like Marilyn Monroe, Audrey Hepburn, and Sophia Loren. Glass cases display some of the company’s colorful and iconic creations—many that seem more sculpture than shoe. There is also a small space that hosts contemporary art exhibitions.
  • 1011 Fort Stockton Dr, San Diego, CA 92103, USA
    Inspired by a former Ford car dealership that once sat on the site in upscale Mission Hills, Fort Oak’s interior mixes old and new; hexagonal tiles and brass accents give the space a vintage feel, while a black oak communal table and plank flooring bring a modern industrial vibe. Executive Chef Brad Wise excels at wood-fired cuisine—the exhibition kitchen has a 7,000-pound grill and range where he fires up 45-day dry-aged ribeye and Australian wagyu beef—but what really sets Fort Oak apart is a raw bar serving seafood towers and buttery hamachi poke. For a decadent night out, slide into Fort Oak’s chef’s counter for a six-course tasting menu cooked by Wise (offered Wednesday and Thursday nights every other week; reserve ahead).
  • Calle Dinamarca 44, Cuauhtémoc, 06600 Ciudad de México, CDMX, Mexico
    A brother-sister expat duo has opened this chic slice of Brooklyn in Colonia Juárez, the neighborhood currently angling to be Mexico City’s hippest. No complaints on that account at Cicatriz, whose open, industrial-styled storefront is a forum for several daily moods. No-compromise coffee and a variety of alternative baked goods form the morning agenda; lunch means a major emphasis on locally sourced greens in great salads and roasted iterations; the meatball and fried-chicken sandwich are both major crowd-pleasers as well. After five, it’s time to get your drink on; the bartenders deliver superior, crafted quaffs, but free from all the fuss you’ll see at other haute mixology spots. The earnest, healthful menu is enhanced by an overall vibe of do-it-yourself chic.
  • 1 Manele Bay Rd, Lanai City, HI 96763, USA
    In 2012, one of the world’s richest men—Oracle founder Larry Ellison—bought 97 percent of the island of Lanai. The single sweeping deal (reputed to cost $300 million) included the exquisite Four Seasons Resort, overlooking a marine reserve. The resort’s dining experience par excellence is Nobu, where celebrity chef Nobuyuki Matsuhisa presides over the perfect marriage of Japanese dishes and Peruvian ingredients. Kick things off with crispy Brussels sprouts or scallops with jalapeño salsa, then move on to sushi, hand rolls, or Wagyu beef. Save room for the Bento Box dessert with green tea ice cream and chocolate flourless cake. Or go old-school, if it’s on the menu, and order the mochi pound cake backed by yuzu-cherry jelly and peanut butter ice cream.