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  • St. John is the least developed and most sparsely populated of the three main islands in the U.S. Virgin Islands. That’s not surprising, since more than half its land is protected as a U.S. National Park. Most visitors reach St. John by ferry from St. Thomas, landing at the dock in Cruz Bay, St. John’s main settlement. A village with only a few thousand residents, Cruz Bay has gained a reputation as an upscale retreat for movie stars and other high-profile people looking for a secluded getaway.

    It all started back in 1956, when businessman and conservationist Laurance Rockefeller, who had bought extensive land holdings on St. John, opened the low-key but luxurious Caneel Bay Resort. It’s still going strong, and visitors can stop in for lunch and a swim in the beautiful bay. Rockefeller later donated much of his estate to the national park.

    Snorkelers should make time for an underwater tour in Trunk Bay, where the National Park Service maintains a submarine snorkeling trail. And no sightseeing drive around the island is complete without a stop to see the fabulous panoramic view from the Bordeaux Mountain Overlook. Back in the town, the boutiques at Mongoose Junction offer one-of-a-kind souvenirs, while Cruz Bay Landing is a perfect spot to grab lunch and drinks.

  • Herengracht 255, 1016 BJ Amsterdam, Netherlands
    For its much-anticipated first outpost outside London, the hip Hoxton boutique hotel brand—named for the trendy hipster neighborhood of its first hotel—chose five 17th- and 18th-century townhouses (including a former mayoral residence) on the canals of the Dutch capital. The brand has a formula that works, but rather than impose its signature style on another city—colonial-style, if you will—the designers have done it the other way around, imposing the buildings’ architectural styles and the city’s aesthetic on the brand. Original parquet floors, beamed ceilings, and wood paneling infuse the midcentury leather furnishings, geometric mirrors, and creatively patterned subway-tiled bathrooms with a Dutch feel, while the turquoise of the canal outside is reflected in the paint. Two rooms have original ceiling frescoes, and five have (non-working) fireplaces. In the ways that count, The Hoxton is true to its brand, such as bespoke toiletries, a scenester restaurant, a trendy bar, and its signature daily breakfast bag with a banana, granola, and orange juice.
  • 15 St Stephen's Green, Dublin, Ireland
    If big museums aren’t your thing, but you’d like to get a flavor of the story of Dublin, drop into the Little Museum on St. Stephen’s Green, which is full of quirky memorabilia from times past in the city, all donated by the public. There are guided tours on the hour, and each tour reveals some of the city’s secrets, with letters from famous literary characters like James Joyce and Samuel Beckett, signed U2 albums, and all sorts of things on display—from badges and newspapers to old signs and even bullets—all of which have a story to tell. Set in a Georgian townhouse, with views out over the green and the excellent Hatch & Sons Irish Kitchen in the basement for post-tour grub, this little space offers a lot to love.
  • 7 Rennweg
    Built on the site of Roman and Celtic ruins, the unassuming 5-star Widder Hotel comprises nine medieval townhouses that were painstakingly renovated over a 10-year period by Swiss architect Tilla Theus. The results are jaw-dropping, from the unusual structures such as circular rooms and passages that refer architecturally to a Roman well uncovered during construction, to the mix of antiques and modern designer furnishings (Eames, Frank Lloyd Wright) in the rooms.

    Alongside the 35 standard rooms, 14 suites also mix the old with the new, featuring works of art by the likes of Robert Rauschenberg and Andy Warhol, contemporary design classics by Le Corbusier and Mies van der Rohe, and original medieval frescoes, exposed-beam ceilings, and brick or stone walls. All rooms are equipped with a TV, Quadriga communication system, and two telephones.

    Widder Hotel also features three great restaurants, a bar with more than 1,000 spirits, and a cozy garden restaurant and lounge open in the warmer months.
  • Piazza Vittorio Emanuele, II, 4, 01030 Calcata VT, Italy
    The government said the cliffs of Calcata, a medieval hill town 30 miles north of Rome, where crumbling and the residents would have to abandon the village for a new one a half mile away. They were right. Sort of. There was a government policy, created during the Fascist era, that stated any village that was so decrepit it was dangerous, the government would destroy it and build a new town nearby. The residents of this cramped hill town, tired of the poor living conditions, took advantage of this law. By the 1960s, the new town, Calcata Nuova, was ready and the old residents slowly moved. At the same time, hippies and artists discovered this slowly abandoned village and bought up the houses, knowing the village was to be condemned. They eventually had the law reversed, saving the village, and went on to fix up Calcata. Today home prices have soared and it’s become one of the most beautiful (and bizarre) places in Italy.
  • 116 Broad St. Charleston, South Carolina
    John Rutledge was an active player in early American politics, signing the Constitution and serving as South Carolina’s first governor. But his townhouse on Broad Street, now the John Rutledge Inn, was built before he even attended his first Continental Congress. The house was embellished and expanded over the years, including the addition of elaborate lacelike ironwork that still stops passersby in their tracks. The inn comprises the main building and two carriage houses. In the 1980s, a major renovation prepared it for its new life as an inn, restoring the parquet floors, marble fireplaces, and crown molding to fully honor the property’s past.

    Rooms in the main house evoke the property’s Colonial Era origins, with canopy beds and brass fireplace screens. All rooms have Tempur-Pedic mattresses, property-wide Wi-Fi, and flat-screen TVs help guests remember that they’re still in the 21st century. Around the property, visit the sumptuous ballroom for evening sherry, or stroll the lush, secluded courtyard.
  • The Paseo
    Gaze at the beautiful floor to ceiling mosaic that pictures the marine life and coral reef in Grand Cayman as you climb the double helix staircase to the top of the 75ft observation tower. Located in Camana Bay, this tower offers 360 degree panoramic views of Seven Mile Beach, George Town, and the North Sound. Not up for the big climb? No worries, there’s a full service elevator available to take you to any floor for observation, including the very top.
  • 2952 Sidco Dr, Nashville, TN 37204, USA
    One of the most popular new breweries in town, Black Abbey Brewing Company opens its “fellowship hall” tasting room Thursday through Sunday. Have a seat at one of the communal tables for a bite of cheese, olives and meats while tasting your way through beers like The Rose, a belgian-style blonde, or The Special, a traditional monastic-style beer. Black Abbey’s brews also are available at many restaurants and bars in town.
  • 7 Weltevreden Street
    Located in the 160-year-old Leinster Hall, The Stack has to be seen to be believed. Its recently refurbished interiors are both outrageous and sublime, with emerald and sapphire walls, a leopard-print couch, and a rainbow of velvet chairs. There’s a beautiful garden out front, a brasserie and bar downstairs, and a private club on the top floor. Dining here feels like you’ve gained entry to a private, Old Cape Town world, but with a modern menu. Standout dishes include the duck rillette and the onion tart with king oyster, shiitake, and shimeji mushrooms.
  • 15 Rose Ave, Venice, CA 90291, USA
    A breezy little beach hotel filled with rough wood, natural linen, and flea market finds, the Rose seems, to the uninitiated, like a pure product of quirky Venice’s hipsterfication. In fact, the historic, wood-and-stucco building was built by the beach town’s founder, Abbot Kinney, in the early days of the 20th century; rumor says it was his private brothel, frequented by such friends as Charlie Chaplin. By the 1970s, at the height of Venice’s drug culture, the building had become a flophouse of sorts, and neighbor Dennis Hopper was known to drop by. Before two British photographers discovered it, the house had turned into a mural-covered crash-pad for surfers, yogis, and beach bums of all kinds.

    Looking at the low-key Rose now—the town’s first true boutique hotel, barely half a block from the beach—one would hardly know that the entire history of Venice had passed through it. The rooms are spare but stylish, with large windows, art photography, and vintage furniture. Some rooms are large enough to live in, whereas others share a hallway bathroom. Amenities are minimal—Stumptown coffee, bicycle rentals—but a relaxed beach house that attracts artists and creatives looking to delve into Venice’s eclectic, vibrant culture doesn’t need to try too hard to be cool.
  • Silo Square, V & A Waterfront, Cape Town, 8801, South Africa
    The new crown jewel of the Cape Town hotel scene, The Silo is housed in an old grain elevator, perched above 42 cement silos on the V&A Waterfront. The silos, which extend outward below the hotel, are home to the world-class Zeitz Museum of Contemporary African Art, opened in September 2017. Inside the hotel, owner Liz Biden seamlessly blends her penchant for bold colors and animal prints with some of the best in contemporary African art. The 28 guest rooms feature handmade headboards and Egyptian crystal chandeliers; concave, floor-to-ceiling windows overlooking the city or harbor; and deep-soaking tubs in the bathroom.

    On the sixth floor, you’ll find the concierge (Hoon Kim, one of only 12 South Africans to hold the coveted Crossed Keys—a distinction from the prestigious hotel concierge association Les Clefs d’Or), the Granary Café, the Willaston Bar, and several private meeting rooms. Also on-site is a spa, gym, and rooftop infinity pool and lounge with views of Table Mountain. If you’re visiting over New Year’s, head to the rooftop—or book a west-facing room—for spectacular views of the V&A Waterfront fireworks.
  • 38 Long St, Cape Town City Centre, Cape Town, 8001, South Africa
    You might hear Long Street before you see it—this bustling artery is the heart of Cape Town, home to some of the city’s most popular restaurants, bars, and boutiques, all within a few blocks’ radius of the Grand Daddy Hotel. Built in 1895, this landmark building has been transformed into one of the city’s quirkier havens, though it somehow manages to walk the fine line between campy and classy. It’s a spot that’s beloved by tourists and locals alike (don’t be surprised to stumble onto a local fashion shoot in the gilded Daddy Cool bar).

    Behind the stately gray exterior lies a whimsical world: snuggle into crisp white sheets in one of the 26 colorful rooms or suites, or settle into a stylishly appointed Airstream in the rooftop trailer park. And speaking of the rooftop: there’s no better place to take in the view of Table Mountain presiding over the city.
  • 19 Buitenkant Street
    One of the best coffee shops in the city, the Haas “Collective” (haas means “rabbit” in Afrikaans) has grown organically over the years to include not only coffee, but also design, art, and advertising. Formerly located in an old slave home in the Bo Kaap, Haas now takes up a refurbished colonial building in the city, where you can also have light meals at the plush yet relaxed venue. Selected artworks for sale include must-have gilded African bowls by Michou.
  • Beach Rd, Chapmans Peak, Noordhoek, 7979, South Africa
    The Red Herring in Noordhoek is a local pub that is a nice place to dine in all seasons. In the summer, you can toast the sunset over Noordhoek Beach from the rooftop balcony (but arrive early to ensure you get a seat). In the winter, you can dine downstairs next to this cozy fireplace. Their pizza is a delicious, too. Their large, crispy pies and rival that of the nearby pub The Toad. The setting and menu are varied enough that you can eat there more than once.
  • Jalan Dato Syed Omar
    The Westin Langkawi Resort & Spa has a lovely pool overlooking the sea. Perfect for relaxing and taking it easy and doing absolutely nothing. But if you do feel like going out and about, the main town, Kuah, and its jetty is pretty close by.