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Hello, rooftop pool! Leave it to Chicagoans to remain optimistic that summer will be amazing, even if winter lasts well into May. The rooftop pool (open to restaurant as well as hotel guests), occupies a prime spot on one corner of Six Points, that crazy intersection where three major shopping streets cross paths. That means the regulars are a mixed bag, but all come in for a good time, whether that means for brunch in the newly redesigned Café Robey street-level restaurant, to drink until dawn at the poolside Cabana Club bar, or to sneak up to its new sister, the Up Room, at the top of the deco tower.

With no sign above its unassuming storefront, Tartine is most easily recognized by the line that snakes out its door and down Guerrero Street. People patiently wait for flaky pains au chocolat (the best outside Paris, in my opinion), decadent banana cream tarts, and hot-pressed sandwiches stuffed with fillings like smoked sheep cheese and quince jam. The bakery’s James Beard Award–winning pastry chefs also turn out loaves of stone hearth–baked bread, available every day after 4:30 p.m. Nurse a coffee and nibble on a croissant at the communal table, or take picnic provisions to nearby Dolores Park.

This former industrial site is a one-stop shopping spot for last-minute souvenirs. Weave in and out of the countless alleys and stalls; among the art galleries, toy shops, crafts stores, farmers market and waterfront restaurants, you’re likely to find something tasty to sample or so unique that you have to bring it home.

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.

This NoMad hotel was developed with a community of influential, savvy travelers in mind. Case in point is the upscale-urban design by studio MAI, which includes both modest and globally-inspired décor (think raw-bronze shelving, rich fabrics, and hand-carved benches in a carefully devised layout to maximize space). MADE Hotel, developed by The Devli Group, also anticipates travelers’ needs with a variety of venues, from Paper (a neighborhood coffee shop serving serious caffeine fixes) to Ferris (a new American eatery with plates like lobster toast with kombu and sesame). If you decide to venture out, the team still has you covered—literally. Sutterheim raincoats and Foak sunglasses are available to rent, rain or shine.

The brick-and-iron warehouses of the old Eveleigh Railway Workshops host a diverse lineup of experimental music, theater, film, and fine art. Located on the border of Redfern and Waterloo, Carriageworks was restored to keep the historical roots intact while providing a space for cutting-edge culture. Every Saturday, more than 70 stalls fill the former railyard outside with organic produce, artisan breads, specialty coffee, and exotic flowers as well as street food from the likes of chef Kylie Kwong during the farmers’ market. Fuel up at the market and then get inspired by whatever is on display inside this artist-run venue. Big annual events for Sydney Contemporary, Pacific Runway, Sydney Gay and Lesbian Mardi Gras, and the Sydney Festival are also held here throughout the year.

Charleston is a relatively small city to sport a food court, and Workshop’s out-of-the-way location on the Peninsula’s Neck underscores that. Situated in a Silicon Valley-esque complex of start-up office spaces, you’ll need to drive to get there, and once at the modern, industrial food hall, you’ll be faced with some tough decisions. The rotating vendors have included Juan Luis, a Tex-Mex spin from BBQ master John Lewis, and seasonal booths where the city’s up-and-coming chefs test out their latest concepts, from Japanese sliders to shareable Indian small plates. Although the vendors change regularly, there’s always a coffee shop, a craft pizza or burger stand, and a variety of ethnic options, making Workshop a must on any dining tour of Charleston’s latest and greatest. It’s also directly adjacent to Edmund’s Oast Brewing Co., a popular hangout and generally regarded among the city’s best breweries.

Right in the center of town, Capri Tiberio Palace mixes la dolce vita glamour with a globe-trotting sensibility that’s equal parts quirky and elegant. Wanderlust-inducing knickknacks such as globes, vintage trunks, and an eclectic collection of art stud the public spaces, and bookshelves are stocked with coffee-table tomes from the publisher Taschen. A white baby grand provides the soundtrack for aperitivo hour at the Jacky Bar, where wicker poufs, striped blue-and-white banquettes, and Panama hats repurposed as wall decor signal vacation vibes; things are slightly more reserved at the terrace restaurant, a formal space whose brightly colored dishes (think seared scallops with almond sauce and beef tartare with chestnut cream as well as kosher fare) are rivaled only by the panoramic views of the island’s craggy peaks coast and azure sea. And the indoor-outdoor swimming pool, though small, is a savior in the summer heat.

When you’re feeling rejuvenated and ready to venture out of Aqua’s quiet beachside retreat, the resort can arrange for you to take a day trip to Granada on the shores of Lake Nicaragua, about an hour and a half drive from the resort. Rich in colonial architecture and colorful buildings, Granada is arguably the most photogenic city in Nicaragua and a popular tourist destination. You can stop at Mombacho Volcano on your way there for zip-lining and a tour of a coffee farm, or at the lake for a boat tour of the isletas, 365 tiny islands that were originally rocks spewed out of Mombacho in an eruption thousands of years ago. Visit the Granada Cathedral and the city’s museums, then wander the narrow streets to admire the old haciendas that have been turned into boutique hotels and artisan shops. Shop for handcrafted leather goods, carved wooden furniture, and hand-woven hammocks that can be easily folded up for the trip home. Photo by Marianna Jamadi.

Housed in side-by-side 19th-century townhouses amid the gas streetlights and cobblestoned streets of Boston‘s Beacon Hill, the high-end Beacon Hill Hotel retains a distinctly European feel. The original owners and neighborhood residents Peter and Cecilia Rait bought the properties with the intent of opening a hotel and bistro. Nowadays, the property is managed by Saunders Hotel Group, but the who’s-who clientele hasn’t changed. Since the hotel opened in 2000, the intimate property has hosted innumerable A-listers seeking a lower profile, including Todd English.

Each of the 13 rooms has plantation shutters, pedestal sinks, flat-panel TVs with DirecTV, and windows that actually open for fresh air. The second-floor common area invites guests to meet and mingle. Plus, the hotel has a private, residential-feeling roof terrace overlooking Charles Street, perfect for morning coffee or afternoon reading.

Despite being located just outside Reykjavik’s main center, the Hilton Nordica maintains its popularity thanks to its superb service and welcoming Scandi-mod interiors. Though working travelers tend to favor the property for its many functional conference rooms and business center, leisure visitors prefer to cozy up in a leather armchair by the fire in the plush neutral-toned lobby. The aesthetic continues in the spacious rooms and suites (the smallest is 300 square feet) with their calming, natural palettes, colorful photos of Reykjavik, and large windows that allow Iceland’s generous light to flood in; suites also enjoy separate lounge areas. The VOX restaurant serves gourmet New Nordic cuisine with an emphasis on Icelandic and Scandinavian ingredients, and the open-concept bar serves coffee, tea, and cocktails, and is a comfortable spot for lounging or mingling whether you’re coming in from a busy day of sightseeing or getting ready to hit the town.

In 2001, hotelier Ian Schrager tapped French designer Philippe Starck to reconceptualize The Clift Royal Sonesta Hotel’s wildly modern interiors. A complete contrast to the building’s historic facade, the lobby is dark, edgy and filled with a quirky smattering of cool furniture—among them chairs by Ray and Charles Eames, a coffee table by Salvador Dali, and a surreal stool by Renee Marguerite. Upstairs, splashes of lavender brighten more neutral rooms, which feature wheelbarrow-shaped chairs and sleigh beds designed by Starck. Merino wool blankets are primed to battle foggy nights, while MALIN+GOETZ bath products soothe well-traveled skin with natural ingredients and science. Downstairs in the Redwood Room, a see-and-be-seen crowd nurses drinks. The swanky lounge sports sleek backlit shelves, its original redwood paneling, and a bar supposedly crafted from a single redwood tree. Though The Clift sits just up the street from Union Square, it feels far away from the tourists.

The Goldberg brothers gave Nashville acclaimed restaurants and bars such as the Catbird Seat and Patterson House, plus a kitschy honky-tonk on Lower Broad. In 2013, they did it again with Pinewood Social, a coffee shop, restaurant, bar, karaoke space, and, yes, bowling alley. There’s even an outdoor pool and bar for when the weather is nice. Amid all the fun, however, don’t forget about the food and drinks served morning, noon, and night, from pot roast and fried chicken to house-made tagliatelle with mushrooms, asparagus, and egg.

Almost any time of day, the Sea Point Promenade is filled with walkers and joggers, many of them residents from the apartments nearby. Though named after Sea Point, the best known of the areas the walkway fronts, the three-mile promenade begins in Granger Bay, closer to the city, then goes past the red-and-white-striped lighthouse of Mouille Point and continues to Sea Point itself (don’t miss the Art Deco Pavilion, site of many international fashion shoots), before curving around to dramatic, Riviera-like Bantry Bay. A path high above the cliffside apartments of Clifton extends for several more miles to Camps Bay. All along the promenade’s way (except along the fairly long Clifton stretch), there are restaurants and coffee shops.

Casa Antucura is an idyllic eight-suite wine lodge with majestic views of the Andes Mountains. Located in the heart of the Uco Valley, the farmhouse-inspired boutique hotel is a remote getaway for relaxing and contemplating Mendoza’s beauty. Characterized by elegance and refinement, the country home was built for guests to enjoy the picturesque working vineyard and its fine wines.

Peruse the lodge’s art collection and expansive second-floor library, which features more than 7,500 multilingual books amassed by the hotel’s French owner. From coffee-table books on travel to celebrated classics, the library has an eclectic collection worth exploring. Grab a book and curl up next to the fireplace in the luminous sitting room, or swim off jet lag in the large outdoor swimming pool surrounded by a beautiful rose garden. For relaxation, book yourself a treatment in the spa.