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  • Otrobanda, Willemstad, Curaçao
    Stroll through Otrobanda for more than five minutes and you’ll immediately understand why locals call it the cultural heart of Willemstad. Located across the bay from Punda—Otrobanda literally means “other side"—the district is a fascinating mishmash of restored colonial buildings and run-down alleys covered in fading murals. Along the Breedestraat, the neighborhood’s main shopping road, you can find rows of Chinese and Indian stores, bars, lotto shacks, bakeries, and hole-in-the-wall restaurants. The best way to explore this area’s complex past is to join Shirley of Dushi Walks on a two-hour trek to her favorite sites—complete with history, art, and stories from the residents you’ll meet along the way.
  • 1095 Hamilton St, Vancouver, BC V6B 5T4, Canada
    Routinely crowned the city’s top seafood restaurant, Blue Water Cafe is also among the continent’s best. After honing his skills at Michelin-starred restaurants in Europe, executive chef Frank Pabst opened this Yaletown classic to marry fine-dining techniques with local, sustainable ingredients. Eventually, the restaurant became a founding member of the Ocean Wise program, which helps consumers make ocean-friendly seafood choices. When visiting, you can belly up to the bar—which boasts more than 200 whiskeys and 1,000 wine labels—or reserve a table in the elegant brick-and-beamed dining room, housed in a heritage warehouse. Come summertime, however, you’ll want to head straight to the patio for sushi and premium sake. Fancy a splurge? Go for the seafood tower, which showcases the bounty of British Columbia.
  • 2706 White Oak Dr, Houston, TX 77007, USA
    Fitzgerald’s has been around since 1977, and has hosted some of the biggest names in music—like James Brown, Tina Turner, and the Ramones—in addition to giving a start to many local bands. The first floor of the two-story building has a full bar, small stage, and large back cobblestone patio with a separate bar. Upstairs is the main stage, accompanied by a full bar, balcony seating, and an inviting hardwood dance floor. Buy tickets online or at the door for shows several nights a week.
  • Cirujano Guzmán 39, Santiago, Providencia 7500513, Región Metropolitana, Chile
    No apologies for screen-staring while you eat or drink here: Insert Coin is all about ingesting entertainment from the multiple arcade games, PlayStations, and Nintendo systems while sipping a novelty drink like a Dive the Tower or a Kong Blast, or munching on the restaurant’s snacky menu. Use the on-table consoles for free as long as you are consuming. Fridays and Saturdays get so busy you might have to wait for a game-equipped table.
  • Astipalea 859 00, Greece
    Spectacular hilltop villages are a dime a dozen on the Greek islands, but Astypalea, a distant speck in the Dodecanese, has the quintessential sugar-cube capital cascading over a rocky outcrop to a sheltered harbor. The oldest houses are huddled along the cliffs circling the Venetian Querini Castle. Castro Bar is built right into the 15th-century castle walls (which look even more dramatic when illuminated by moonlight). A series of small terraces on different levels, painted in white, burgundy, and blue, all offer stupendous views across the island and what feels like the whole Aegean. The vibe is mellow, and the drinks are strong. Stay until the sun rises out of the sea, a trippy experience you won’t forget.
  • 1150 Queen St W, Toronto, ON M6J 1J3, Canada
    Usually, when you travel, it’s to experience a different side of yourself. The more adventurous side, the slightly less scheduled side, the sleep-in-without-guilt side. And when you stay at the Drake Hotel in Toronto, you can’t help but feel like your cooler side is making a much-needed appearance. The recently renovated property on Queen Street West features the kind of interior design that radiates style whether it’s in the kaleidoscopic lobby, the next door theater, or in two wings of suites. That’s because the hotel commissioned artists to showcase their work on plenty of open surfaces — from a black-and-white squiggle accent wall in guest rooms to personality-driven drawings in the elevator — and the results make for surroundings that are the material equivalent of black sunglasses. Paired with of-the-moment details like pink terrazzo showers and wraparound midcentury sofas, and the Drake Hotel is meant to cultivate a see-and-be-seen vibe.

    But that’s not to say that the hotel sacrifices comfort for being camera-ready. The staff is kind and always available through text, the beds are soft and squarely stationed in front of a well-appointed bar and flatscreen television, and designer toiletries are filled to the brim. It’s also possible to eat throughout the day at the hotel’s delicious cafe and patio (get the French toast), and then spend the night at its second-floor bar or ground floor lounge. On weekends, even if you’re not a guest, you can stop by for regularly scheduled events including a DJ who spins old and new tunes. If you do plan on leaving the hotel to see the city, then you’re right in the midst of it, and the surrounding neighborhood can keep you readily entertained.

    When you stay at the Drake Hotel, don’t be surprised if you feel relaxed, in-the-know, and decidedly cooler once you check out. These are sides of yourself the hotel may have encouraged, but feel free to hold on to them after you return home.
  • Calle Benito Juárez SN, Centro, 23033 Todos Santos, B.C.S., Mexico
    “Dude” is a word that’s used a lot around Rancho Pescadero, a small hotel in the surfing town of Todos Santos, located in the Mexican state of Baja California. The rooms here, however, don’t reflect the dude aesthetic, which is to say they are clean and classy. Spacious suites offer comfortable spots to relax, with most having retractable glass doors that eliminate barriers between indoors and outdoors and open up onto terraces that have hammocks or lounge beds. Terra-cotta tile floors, rattan and wood furniture, and locally made accents—such as hand-embroidered throw pillows—are some of the decor elements found in rooms. Surfers won’t feel totally out of their element, though; world-famous breaks are less than 10 minutes away and staff can give pointers on the best spots to hang ten. Apart from surfing, the hotel encourages guests to spend a lot of time relaxing and immersing themselves in the laid-back Baja lifestyle.
  • 3815 N Brown Ave, Scottsdale, AZ 85251, USA
    You will want reservations to get into this place. The Mission Restaurant and Lounge serves modern Latin cuisine in a fantastic bar restaurant with a wonderful outdoor back patio (seen here). The chef is Matthew Carter, also known for the House and Zinc Bistro. For desserts, order the pumpkin bread pudding with scotch, pepitas, and pomegranate.
  • Santa Korda Kalea, 4, 20003 Donostia, Gipuzkoa, Spain
    At La Cuchara de San Telmo, on the corner of the plaza Valle Lersundi in San Sebastian, the specialties were hot pintxos, quickly prepared to order--from the menu or the specials board, or by pointing to what your neighbor was eating. This was one of best scallops I have ever tasted. But then, so was the second one we had when we returned after another hour or so of pintxo bar hopping in the Parte Vieja (Old Town).
  • Nik. Nomikou (Main Street), Oía 847 02, Greece
    Nothing says Santorini like an aqua-blue infinity pool, and Katikies has three of them—all the better to take in westward-facing sunset views. Carved out of the cliff side 300 feet above the Aegean, the hotel’s public spaces are connected by a series of bridges and Escher-esque stairways as they descend from the town of Oia above it. Cube-shaped rooms and suites are minimalist but inviting, nearly every surface painted or clothed in calming white; all have verandas, while a few large suites have outdoor plunge pools or Jacuzzi tubs and alfresco seating areas. Upon check-in, guests are given cell phones to summon 24/7 service from anywhere on the property. They use them to order light snacks at the poolside bar and restaurant or make reservations for some of the best sushi on the island at the champagne bar, but the candlelit rooftop restaurant—serving Greek and Anatolian cuisine—is about as romantic as it gets.
  • Ul. Jurja Barakovića 5, 23000, Zadar, Croatia
    Zadar’s antiques market is located in the old town, on Jurja Barakovića Street, and open daily from 9 a.m. to 1 p.m. and then again from 3 p.m. to 8 p.m. Military memorabilia from the days of Yugoslavia and earlier is popular, but that’s just a small part of the selection you’ll find for sale here. There are also many lovely glass pieces—goblets, beads and objets d’art.
  • 4A Palmotićeva ulica
    Wine is an integral part of life on the Dalmatian Coast, a region with many indigenous varietals; a visit to Dubrovnik shouldn’t go by without a glass of local wine. Tucked away on Palmotićeva Street off the main Stradun, D’Vino offers cozy interiors as well as atmospheric seating at tables set on the narrow thoroughfare outside. Try a glass of something new from the impressive selection of local producers—the knowledgeable staff can help guide you in choosing one. D’Vino features several tasting experiences that highlight the region’s star wines: the Konavle Valley’s refreshing Malvazija, potent Plavac Mali reds from the Pelješac Peninsula, and Korčula Island’s fruity Pošip whites. Pair the wines with a platter of prosciutto and Croatian cheeses for a wonderful welcome to Dubrovnik and its wine region.
  • 5632 Santa Monica Blvd, Los Angeles, CA 90038, USA
    When owner Dave Neupert discovered the history of the Gold-Diggers Entertainment building in East Hollywood, he knew he had to turn it into a music-themed bar and boutique hotel. Originally built as an “inn above a tavern” in 1924, directly on Santa Monica Boulevard back when it was the famous Route 66, the building later became a dive bar with a rehearsal studio in the back that welcomed punk bands and was even used as a sound stage for Ed Wood. Now, the sleek Gold-Diggers bar includes dark-wood chevron paneling, textured wall coverings, a gold-velvet stage curtain, and Art Deco pendant lighting. Justin Gage of Aquarium Drunkard oversees the music and has welcomed such musicians as Iceage, Mary Lattimore, Julianna Barwick, and Luna to perform. There’s also an on-site recording studio, featuring nine professionally designed and acoustically engineered writing, tracking, and mixing studios managed by industry veteran Simon Horrocks and Grammy-award-winning engineer Eric Gorman.
  • Praça Luís de Camões 2, 1200-243 Lisboa, Portugal
    What a wonderful location to stay in Lisbon—in the middle of an elegant neighborhood like Chiado and so close to the trendy Bairro Alto. A five-star boutique hotel, this place is full of charm and luxurious rooms spread across five floors, with views over Largo do Camões and the river. A building from the 18th century, this hotel, with décor by Portuguese designers, features dark wood furniture, mixing classic and contemporary. Visit the bar on the rooftop; it is one of the best spots for a drink with a view.
  • 12 S Michigan Ave, Chicago, IL 60603
    This hotel is on our list of The 11 Best Hotels in Chicago.

    Set directly across from the Art Institute of Chicago, this former members-only men’s gymnasium is now the Chicago Athletic Association, which is part of Hyatt’s Unbound Collection. Enter at street level off Michigan Avenue and walk toward the back to find a staircase that leads to the old swimming pool, now a venue for parties and pop-up concepts. Take the nearby elevator to the restaurant, Cindy’s, easily the best rooftop scene in the city, with highly Instagrammable terrace views overlooking Millennium Park, the swooping Frank Gehry–designed bandshell, and Anish Kapoor’s Cloud Gate (aka the Bean).

    Park yourself in the second-floor lobby and hang with locals as they tap away on their laptops and sip lattes by the two oversize fireplaces. Walk through that expansive by Roman & Williams–designed room, where light beams in through ornate stained-glass windows, and you enter a warren of table games and darts, all festive and typically open to the public. There’s also the secret six-seat bar, the Milk Room, a relic of Prohibition, and the James Beard Award–winning Cherry Circle Room—a sexy, dark restaurant with a circulating martini cart and a meat-centric menu.

    Upstairs in the 1893 landmark, 240 guest rooms reflect the building’s former life, with gym horses as foot beds, working fireplaces in some rooms, plasterwork ceilings, ornate carved wood wainscotting, and a clubby vibe. Some of the rooms are rather small, but the location is hard to beat, and the cozy, wintry ambiance makes it a popular (and fun) place to spend a weekend. And because the CAA keeps an eye on its water conservation, sources its food locally, and adheres to strict recycling standards, eco-conscious travelers can feel good sleeping here.