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  • When I first moved to the island, I joined a friend in the Old City for a tour and lesson on the history of Puerto Rico. When passing by this little section of town near Pigeon Park, my friend and native-turned-tour-guide said that this was the smallest house in Old San Juan. Wow, okay, so this little yellow portion is technically a house? I’ve visited this site several more times since then and have never actually seen anyone enter or leave this door. Whether it’s true or not, it makes for a cool story and great photo.
  • Las Terrenas 32000, Dominican Republic
    Located on the Samaná Peninsula, 300 feet above Playa Cosón and the Atlantic Ocean, this 18th-century, plantation-style home impresses with Victorian trim and wraparound terraces perfect for sipping cocktails in the shade. Inside, antiques from Asia, Europe, and Turkey; rugs from Istanbul; and details like Brazilian hardwood floors and French doors add further charm. The six guestrooms, all housed on the second floor, feature four-poster beds, mahogany soaking tubs, and private terraces—rooms 5 and 6 have the best ocean views.

    Breakfast and dinner are served on vintage china in the main house, while lunch takes place a seven-minute shuttle ride away at the Beach Club. This is where you’ll also find the inn’s pristine beach, a nearly 90-foot stretch of sand that’s mostly empty, great for swimming, and considered one of the country’s best places for kiteboarding. When you’re not lounging here, visit the town of Las Terrenas (just 10 minutes away) or try to spot the humpback whales that migrate from as far off as Greenland and Iceland to mate and calve in the warm waters surrounding the Samaná Peninsula (every January through March).
  • 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.
  • Bennelong Point, Sydney NSW 2000, Australia
    Designed by Danish architect Jørn Utzon, the Sydney Opera House was inspired by its dramatic setting on Bennelong Point in Sydney Harbour, a location that’s long been sacred to the native Gadigal people. While construction took 16 years, including four years to figure out the spherical solution to the icon’s soaring sails, any controversies melted away when the masterpiece was completed in 1973. The same outside-the-box thinking that built the shell-shaped sculpture seeps through its walls today in the form of boundary-pushing opera, theater, and dance as well as contemporary music and mind-opening lectures. The landmark is also home to the beloved Opera Bar and Bennelong Restaurant upstairs, where diners can eat pavlova shaped like the landmark in which they sit.
  • 1000 Mountain Rest Rd., New Paltz, New York
    A historic New York state resort, Mohonk Mountain House first opened in 1869 in the Hudson Valley, about 90 miles from New York City. This Victorian castle has welcomed five U.S. presidents (including Bill Clinton) in addition to countless artists, authors, and actors. Surrounded by thousands of acres of nature, the resort is perched on a cliff overlooking Mohonk Lake. Guests travel specifically for the dramatic, vibrant fall foliage and expertly manicured gardens. Rates are all-inclusive and comprehensive—all meals and activities are included for a single nightly rate. Yoga classes, boating, tennis, horseback riding, and rock climbing are all popular activities. During the winter, ice skating and cross-country skiing lure guests into the great outdoors. Rooms with wood-burning fireplaces and a huge spa with heated indoor and outdoor pool create a peaceful retreat.
  • 1222 4th Ave N, Nashville, TN 37208, USA
    Locals love the Sunday Supper at City House, when chef-owner Tandy Wilson serves his highly creative Italian-influenced menu, but you really can’t go wrong any night here. Wilson, a 2016 James Beard Award winner, is a Nashville native who spent time in Italy and California before opening his restaurant in the former home of a sculptor in the trendy Germantown neighborhood. Since then, he’s been drawing visitors and locals alike with his belly ham pizzas, corn bread gnocchi, and main dishes like roasted chicken and corn meal–crusted catfish with peppers, garlic, anchovy, lemon, and parsley. Those in the know bookend their visits with a perfectly crafted cocktail at the bar and a dessert from pastry chef Rebekah Turshen, like the almond ricotta skillet cake with lemon marmalade and lemon ricotta gelato.
  • Torstraße 1, 10119 Berlin, Germany
    Looming over one of central Berlin’s most vibrant intersections, this restored Bauhaus building with its distinctive 1920s curved facade was transformed in 2010 into the Berlin outpost of the glamorous Soho House hotel and private members brand. The building has heaps of history, having started as a Jewish-owned department store before being taken over by the Nazis and then occupied by the Communist regime for archival purposes.

    Today, it’s one of Mitte’s foremost havens of hip, offering quirkily decorated rooms that mix vintage with contemporary design tropes—think Marshall speakers and old-school record players, floral armchairs, and art deco bathtubs. The lofts are even more astonishing, both for their capacious size and their industrial-chic aesthetic—some come with grand pianos and foosball tables. The hotel also has a rooftop pool and adjacent bar with views of Alexanderplatz, a concept retail area, a private cinema and library room with a bar that hosts occasional events open to the public, an in-house restaurant, and a Cowshed spa that’s a popular destination in its own right.
  • 1113 Smith St, Honolulu, HI 96817, USA
    From the dingy exterior, you might expect Little Village Noodle House to be a hole-in-the-wall, but it’s surprisingly cute and nicely decorated inside, with fountains, decorative woodwork, and nice tables and chairs. The chef’s special fried rice is justifiably a signature dish: piled high with pork, shrimp, duck, egg, and other goodies. The orange chicken was intensely citrusy with lots of orange flavor — but not that gross, sickly-sweet syrupy coating that usually makes the dish a soggy mess. Lunch items are around $10-12, and portions are decent, though not huge. Considering the unexpectedly fancy decor and fast, friendly service, this is a great choice for a meal in Honolulu‘s Chinatown.
  • 7111 E 5th Ave, Scottsdale, AZ 85251, USA
    A contemporary take on a traditional pub, Citizen Public House is known for its craft beers, classic and modern cocktails, and interesting pub grub. Snacks include bacon-fat popcorn and a beer fondue made with the local Kilt Lifter brew. Main courses like short ribs with a coffee rub and pan-seared scallops with grits are hearty and delicious. The spot is beautiful, too, with mahogany furniture, oversize leather booths, and a large stainless steel–topped center bar. Speaking of the bar—Citizen Public House is a good spot to tip one back with the locals. Because the bar supports Arizona brewers and wineries, you’ll find Four Peaks Hop Knot IPA and Pillsbury Wild Child white blend on the list, along with wines from Caduceus Cellars and Dos Cabezas.
  • 31 Leeson Close
    Ask someone who’s stayed at Number 31, a downtown Dublin house-hotel, what it’s like and he or she likely won’t get past the breakfast: the pears poached in vanilla syrup, Wexford strawberries, eggs scrambled with smoked salmon from the west coast, and slices of zesty cranberry loaf. Such homey food served in a sunlit dining room is part of what makes Number 31 feel less like a hotel and more like the pied-à-terre you’ve always dreamed of. Comfortable rooms and unobtrusive staff add to the urban townhouse vibe; the hotel owners, Noel and Deirdre Comer, manage to be warm and welcoming while also leaving guests to make themselves at home around the peat fire in the sunken lounge.

    A wild garden separates the hotel’s two buildings, a Georgian terrace house and the coach house, and the overall modernist-meets-classic design owes to architect Sam Stephenson, who lived in the house as he renovated it in the 1950s. Number 31 is a favorite of Dublin insiders, from artists to architects to the designer John Rocha.
  • 7011 E Indian School Rd, Scottsdale, AZ 85251, USA
    Tis the season to be jolly! If you’re feeling festive around the holidays or perhaps you want to keep Christmas going all year long, then a visit to the Coach House should be on your holiday wish list. When the holiday season approaches, Scottsdale locals make a trip to their favorite local watering hole to experience a festive spirit unlike anywhere else. Staffers shut down the joint for a few days in order to deck the bar from head to toe with wrapping paper, tinsel, ornaments and twinkle lights that overtake you with Christmas cheer. The bartenders and staff are laid back, friendly and really love what they do. Note: This place can get packed during the holiday season on a late Friday or Saturday night. And, the lights stay up all year!
  • 49 Village Run Circle
    For those of the sporting lifestyle with discerning taste, this local boutique houses European brands of elegant and decadent alpine chic wear. There are very rare finds, from rich leather blazers embellished with horn detailing, to handmade, embroidered Austrian cashmere ski sweaters. It also dabbles in mountain lifestyle décor with furnishings, dishware, and fixtures to outfit any house in to the ultimate Colorado ski lodge.
  • Shanagarry, Midleton, Co. Cork, Ireland
    Myrtle Allen is Ireland’s answer to Alice Waters: The centenarian chef has lobbied the Irish parliament for better food policies, earned some Michelin stars, and, 50 years ago, opened a restaurant called the Yeats Room in the town of Shanagarry, an hour east of Cork City. She eventually added bedrooms upstairs and called it Ballymaloe House, and her sous-chef-turned-daughter-in-law, Darina Allen—who has written canonical Irish cookbooks and helped lead Ireland’s Slow Food movement—tacked on the Ballymaloe Cookery School and farm two miles from the main house.

    This is thus the seat of Ireland’s food royalty, and it shows. The restaurant spins flavorful dinners out of whatever comes in from the farm or East Cork’s fishing boats, and the cookery school has become known the world over for teaching expert and novice chefs to make pizzas, ferment pickles, cook baby food, and grow fruits, vegetables, and herbs. Even without all that, the ivy-fronted house—and cabins and cottages on the farm’s grounds—make for a simple, pleasant country retreat.
  • 118 7th Ave N, Nashville, TN 37203, USA
    In a fantastic location just a few minutes walk from the Honky Tonks lining Broadway, Holston House Nashville is a fun new Music City sleep that also happens to be very dog friendly (this author’s service dog, Bobbi, had a fabulous visit). And if you’re traveling without pup, but find yourself in need of a little canine loving, don’t fear, the Holston House has plans to adopt a house dog, who will reside at the property. The hotel, which is part of the Unbound Collection by Hyatt, has partnered with Miranda Lambert’s non-profit MuttNation that promotes and facilitates the adoption of shelter pets and will adopt the pup through this organization. Additionally, MuttNation receives 100% of the fees the hotel charges for your pup’s stay.

    Dogs aside, the Holston House is an eye-catching meticulously restored 1920s Art Deco boutique property that comes with a side of modern country flourishes like sliding barn doors. Even the standard rooms are quite spacious for a city sleep with the most delightfully comfortable beds draped in silky sheets and soft duvets and plenty of light streaming in from big windows overlooking the city. The bathrooms are massive with toilets separate from the shower space. There are also four plush one-bedroom suites and two signature 12th-floor Penthouse Suites that are massive and come with stunning views and catchy decor.

    The food and beverage program here is excellent with the signature restaurant serving up hearty portions of southern American comfort fare that is hard to stop eating: it is that good. The TENN Bar is responsible for the delightful craft cocktail menu that includes a number of locally distilled spirit choices served in a speakeasy style environment overlooking the lobby with a performance stage for live music. Up on the rooftop you’ll find TENN on Top, the bar next to the vibey outdoor swimming pool — it becomes quite the scene on hot summer weekends, although it is not open to the public — that offers stunning city views and more drinks from the in-house mixologist.

    Away from the hotel there is much to experience in Nashville, where country music stars from Taylor Swift to Blake Shelton got their starts, including amazing live music at seemingly every bar on Broadway. And country music aside, Nashville is one of America’s top music cities in general and is home to Jack White’s Third Man Records Studio where visitors can cut their own track on a 33 RPM single using the 1947 Voice-O-Graph recording booth White first debuted with Neil Young on the Tonight Show with Jimmy Fallon for just $20.
  • 72 Andrew Lane
    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.