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  • İstiklal Ave
    The lifeblood of modern Istanbul is the two-mile-long pedestrian street Istiklal Caddesi (Independence Avenue), running from Taksim Square to the Tünel train station. It’s equal parts touristy and local, commerce and culture, and strolling down the avenue to shop, dine, or just socialize is a favorite pastime of many Istanbullus. (The beloved red-and-white tram is out of service for the foreseeable future while the street gets some much-needed maintenance.) Though many complain about encroaching international chain stores and shopping malls taking the thoroughfare’s distinct character away, there are still plenty of gems if you follow the backstreets and duck into the historic passages. Don’t forget to look up: Many of the art nouveau and Ottoman-era buildings house rooftop cafés and businesses above street level.
  • 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.
  • Rue de la Liberté, Marrakech 40000, Morocco
    Often described as a “Little Paris,” Gueliz has grown into itself in recent years with many of the city’s designers and restaurant owners choosing to set up their flagship fronts there. The Rue de la Liberté is now shoulder to shoulder with fashionable restaurants such as Kechmara for live music, cold beers, and killer burgers; Bistrot Le Loft for platters of French cheese and charcuterie; and the swanky new Asian Resto-Lounge for Chinese steamed dumplings, sushi, and Thai classics; as well as the wine bar Le 68. There’s a Caudalie Spa for great pep-up facials and some must-visit boutiques for snagging made-in-Morocco gifts. Try Lalla, just across the junction at Boulevard el Mansour Eddahbi, for must-have handbags, weekenders, and clutches; Patisserie Al Jawda for delectable Moroccan pastries to take home; and Sidi Marrakech for men’s tailoring. Cross over the main boulevard Mohammed V, and you’ll hit Atika for Tod’s-style suede loafers—brilliant for traveling—in a kaleidoscope of colors. Then hit the Rue Vieux Marrakchi, home to stalwart Moor, for natty embroidered kaftans and cushions, and the envelope-pushing David Bloch Gallery, which showcases the best contemporary urban artists from North Africa.
  • 28r Via di Mezzo
    Italy never had Prohibition (can you imagine the country going wine-free?), but this intimate bar, opened in 2017, brings a touch of that era’s speakeasy style to central Florence. Owner and veteran bartender Cristian Guitti places equal importance on taste and aesthetics, creating concoctions that both excite the palate—with a hint of smoke here, and some barrel aging there—and also do your Instagram proud. The menu is heavily inspired by ‘20s-era cocktails, with nods to both America and Italy, so you’ll find drinks like Old Sport (based on Wild Turkey 81 Bourbon), Coney Island (rum with popcorn, chili, dark chocolate, and more), and Aglio Olio & Peperoncino (tequila blanco with olive oil and the essential oils of orange and chili). Guitti considers this a “cocktail experience,” which means the multi-step drinks may take a while to be prepared, but you’ll have fun soaking up the retro atmosphere while waiting for them to arrive.
  • 100 E Colorado Ave, Telluride, CO 81435, USA
    A Telluride favorite since 1978, Last Dollar Saloon is renowned for two things: $5 margaritas (made with agave tequila and served in a pint glass) and an eclectic selection of beers from all over the world (more than 60 at last count). Start your evening on the right note at the bar’s popular happy hour, which goes from 3 to 5 p.m. and includes four Telluride Brewing Company beers for just $4 each.
  • 31740 Mulholland Hwy, Malibu, CA 90265, USA
    Wind through the Santa Monica Mountains to Malibu Wines, a grassy garden retreat with gorgeous views for picnicking and sipping wine with friends. The space is accented by Instagrammable features like the metal WINE sculpture that emulates the iconic LOVE sculptures by artist Robert Indiana that are found in cities around the world. Entry is free; just order wine from the farmhouse-style tasting room and enjoy the live music and festive atmosphere on the weekends. (Weekdays are more mellow.) Table reservations, including one inside a vintage school bus, are recommended for groups—but if you’re more flexible, simply bring a blanket and some food, find a spot to spread out on the lawn, and explore the grounds.
  • 8639 Lincoln Blvd, Los Angeles, CA 90045, USA
    Hotel June is a fairly new addition to L.A.’s hotel scene, but the historic Malibu spot, which re-opened in 2022 and was once home to Bob Dylan, has swiftly risen up the ranks. Why? For one, its minimalist design offers a calm, relaxing respite from the hectic Southern Californian lifestyle—while also paying homage to its ‘60s roots. There are only 13 bungalow-style rooms, and the vibe is strictly laid back. Private patios feature hammocks, a small pool invites you for a dip, and nearby beaches and trails offer outdoor exploration.
  • 12, Kings Court, Glasgow G1 5RB, UK
    An air of casual cool permeates the atmosphere at this, one of Glasgow’s best gathering spots for fans of alternative music. A judiciously curated events schedule runs the gamut from book readings to live performances, while the cafe serves great vegan food and a wide selection of beer and wine. In house record store Monorail has a small but excellent choice of sounds.
  • 205 Meeting St, Charleston, SC 29401, USA
    The largest luxury hotel in the city, the Charleston Place takes up a full city block with entrances on King and Meeting streets; the latter leads to the grand lobby, with its imperial open-arm staircase, 12-foot crystal chandelier, and Italian marble floors. Its 433 large guest rooms have old-fashioned Southern details like mahogany and damask furnishings. The hotel’s lower level houses fine-dining restaurant Charleston Grill, an attractive hotel bar, a large indoor saltwater pool with a retractable glass roof, and a shopping arcade with designer stores. The hotel recently began a $150 million renovation but will remain open as the property is upgraded from stem to stern.
  • 615 2nd Ave S, Minneapolis, MN 55402, USA
    This boutique hotel in the downtown business district exudes timeless class, with accents of wood and leather throughout. While the rooms are spacious and elegant, the most impressive features are the amenities. They rebooted the hotel’s historic 1915 beginnings as the Minneapolis Athletic Club with a massive modern fitness center, including a full indoor six-lane lap pool, running track, and racquetball, handball, and squash courts. The swanky hotel lobby serves food and drinks from the infusion specialists at Six15 and has a complimentary wine reception hour for guests each night.
  • 1 Stocking Island | Volleyball Beach Stocking Island, The Bahamas
    At Chat ‘N’ Chill, a beach bar on Stocking Island in the Exumas, you can enjoy cold drinks with your feet in the sand and eat your fill of local fare like BBQ ribs and grilled fish. The menu also has burgers, hot dogs, and made-to-order conch salad. This laid-back spot is a classic island beach bar, and you can even wade into the clear water to feed the conch scraps to the local stingrays. Chat ‘N’ Chill is also famous for its Sunday pig roasts, a lively event with a whole, slow-smoked pig, drinks, and island music on the beach.
  • 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).
  • 186 Concord Street
    Chef Drew Hedlund combines classic and contemporary Southern fare here in a retired 1940s naval building on the east side of the Charleston peninsula. Long used for storage by the South Carolina Port Authority, today it’s home to one of the city’s most popular waterfront restaurants, with incomparable views of the harbor. Some highlights of the menu include crispy whole flounder with apricot glaze, Charleston shrimp and grits, crab cakes, Lowcountry boil and lump crab bruschetta.
  • 14 Rue Crespin du Gast, 75011 Paris, France
    We admit, it’s not the easiest place to find—the entrance is through an unmarked door on a bland residential street in Menilmontant. But once you do (hint: look for the velvet rope) and take the elevator seven floors up, you’ll be rewarded with 360-degree views of Paris from the sprawling rooftop. You can sit at communal picnic tables or lounge on comfy sofas, but get there early (it opens at 6 p.m. weekdays) or late to ensure a seat. Beer and wine are your best bets. There is also a restaurant one floor below.
  • 13D Kloof Nek Rd, Gardens, Cape Town, 8001, South Africa
    The Power and the Glory is a cool bistro in the center of Cape Town that has attracted a cult following among locals. The relaxed style, the bearded staff, the folding chairs, and the sidewalk stools may remind you of a Brooklyn cafe. If you can snag a chair, it makes for a great place to work or to have a meeting over a light breakfast. In the evening, the place is usually packed with revelers. Try the quiche in the morning, the pretzel bun hot dog in the evening, and the Nutella cheesecake for dessert.