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The Old Town’s main street, Stradun, also known as Placa, can’t be missed—it’s the biggest and widest of all the thoroughfares, and you will probably walk it several times during your stay here. It’s especially nice in the late afternoon, when the angle of the sun makes the pavement shine and the swallows soar overhead. Continue down to the old port and along the waterfront to the far end. Porporela Pier, built courtesy of the Austrian administration’s rule in Dubrovnik during the 19th century, is today somewhat of a lovers’ rendezvous. After your stroll, the benches along the pier provide a simple relaxing moment to take in the views of Lokrum island and Cavtat in the distance.

Galeries Lafayette Haussmann is worth a visit if only to stand under its magnificent glass dome. The family business has survived as a one-stop-shopping hub for five generations, thanks to steady innovation and an emphasis on high fashion and design. Shoppers appreciate its easy VAT refund policy. There are also multiple restaurants, a rooftop terrace with stunning city views and a cultural space for rotating art exhibitions.

Not every celebrity who visits Harbour Island stays at the Pink Sands Hotel. Bill Gates, for instance, has his own home on the island. But Keith Richards has checked in here, as have Martha Stewart and Kate Moss. Since its opening in the 1950s, the 25-room hotel, like the island itself, has been a low-key enclave of the rich and famous, drawn not just by the like-attracts-like vibe (one of the previous owners was Island Records founder and Bob Marley “discoverer” Chris Blackwell), but by its location on Pink Sands Beach, widely considered one of the world’s prettiest. Accommodations are in plush one- and two-room cottages that have king beds and ocean or garden views; some have outdoor showers. Reserve a table at the British-colonial–inspired Malcolm 51 for island-style bouillabaisse and charred octopus salad, but don’t get too carried away with the sundowners. All manner of aquatic activities (snorkeling the nearby coral reef, bonefishing in the shallows, or merely swimming in the heated freshwater pool) await in the morning.

After strolling through the Prague Castle complex and seeing the Cathedral and square, the traveler is further rewarded with a beautiful view of the city from a high point. Parts of Lesser Town can be seen among the sea of red-orange rooftops and greenery.

Ontario has another wine destination, Prince Edward County, affectionately named “The County.” This cluster of towns, about 2.5 hours east of Toronto, is home to some of Ontario’s best wineries. But never was there a great place to stay until summer 2015 when Jeff Stober, the hotelier behind Toronto’s stylish Drake Hotel, opened a rural clone, the Drake Devonshire. It’s the ideal retreat for travelers wanting their Drake by Lake Ontario. Once a 19^th-century foundry, the building is now a contemporary farmhouse-cottage, decked out with 11 individually-designed hotel rooms and two suites in the quaint town of Wellington. The property offers coziness all year round in the communal living room and out back over a lakeside fire pit and s’mores. Guests can hang in the barnlike Pavilion for musical performances, sommelier seminars, seasonal events, or just to gawk at the floor-to-ceiling mural by Brooklyn artist FAILE. It doesn’t hurt that Sandbanks Provincial Park—known for its 60-foot sand dunes—is practically the backyard of the Drake Dev.

Sound Table is a true food and beverage bar, rewarding members of the industry every Tuesday night with dinner and drink specials. For the rest of the working masses, the Sound Table is focused on cocktails and its award winning bar program with accompanying food menu. All drinks are sorted by flavor profile, whether you prefer sours and citrus or bright and dry.

Along the glittery street of Collins Avenue in South Beach is the Raleigh Hotel, a smart and stylish blend between sparkling lights of Miami and the rich history that old Florida is known for. Immerse yourself in the calming and relaxing vibe of the hotel from the moment you enter the the lobby. Sip a martini at the bar that has been serving shaken cocktails for nearly 50 years.

Take a seat on one of the plush couches and get into the luxurious and sensual atmosphere that keeps South Beach at the top of its game. If you are hungry, make your way to the outdoor restaurant, Restaurant Michael Schwartz located along the twinkly lit bar on the patio. Chef Michael Schwartz helms the kitchen, using farm fresh ingredients and local seafood.

Once you are finished sampling the variety of specialty cocktails with fresh smoked herbs and prime liquors along with crispy crab cakes and shrimp toast, head to the expansive pool patio, which seems to go on forever. It is commonly known as the most famous pool in Miami.

The Raleigh is most well known for hosting Miami Swim Week, where the top names in fashion will sit along the twinkling trees and poolside cabanas to view the next seasons swimsuit trends.

One of the South’s top art institutions, the High Museum was established in 1905 with a collection of European works. Over time, it has expanded to include modern art, regional artists, and rotating exhibits on everything from designer sneakers to the Terracotta Warriors to the Louvre’s most notable works. Outside, guests can view Rodin’s famous sculpture The Shade, which serves as a memorial to the 106 art patrons from Atlanta who died in a plane crash in 1962. Also outdoors are several interactive exhibits that encourage visitors to get up-close-and-personal with the art.

Oenophiles exploring South Africa’s Cape Winelands have a fashionable new place to rest their heads. In the gallery- and boutique-filled village of Franschhoek, Leeu House is a Cape Dutch–style building decorated with a breezy countryside aesthetic. The 12 individually styled rooms have neutral hues, sisal and oak accents, and marble bathrooms; two suites have private gardens. After a stroll through town or a trip to the surrounding wineries, guests can cool off in the hotel’s mosaic pool before heading to its glass-ceilinged Conservatory for such seasonal dishes as masala-spiced yellowtail, caught off Cape Point. Hoping to get even closer to the vineyards? A sister property, the 17-suite Leeu Estates, opens in June on the grounds of a first-class winery of the same name, just a three-minute tuk-tuk ride away. Doubles from $220, including breakfast

If you’re hoping to see all of Laguna in a short amount of time, hop on the free trolley, which runs in five neighborhoods during the week and along the Coast Highway on weekends. Hours vary by day and season, but are long enough to make the trolley a fun, convenient way to get around town. For special occasions from September through mid-June, you can even charter a trolley for a tour or a memorable ride to your event.

Bontemps Pâtisserie may have a name inspired by the fictional Louisiana town from the vampire series True Blood, but this retro-chic bakery is French through and through. The pâtisserie offers a refreshing twist on the signature French sable, a classic shortbread cookie, by using seasonal fillings (wild strawberry, passion fruit, blood orange). Don’t miss the larger tartes, from pecan to apple, which use the same light and crumbly shortbread crust. Take a box of minis to the Square du Temple across the street for an al fresco goûter.

Barba offers a fresh take on fast food, serving tasty items like octopus and shrimp burgers, anchovy sandwiches, and fried calamari, all made with today’s catch. Located on a small side street off Stradun, the shop is tiny and friendly—the perfect pit stop during a day of Dubrovnik sightseeing. Snag the prime table by the front window and watch the rivers of people entering town through the Buža Gate as you eat. Then, be sure to contribute to the restaurant’s growing collection of wooden forks, on which customers from all over the world write messages commemorating their travels.

After strolling Storm King Art Center or DIA Beacon, Tarry Lodge is the perfect stop on your way back to New York City. Mario Batali opened it up as a neighborhood restaurant for the Port Chester crowd and a go-to for out-of-town Manhattanites who love his Italian comfort food. Don’t miss the clam, chili, and oregano or pistachio and goat cheese pizzas. Waits can be long so if you’re trying to beat traffic just get take out from their curbside service.

Everybody loves the highs and lows of Bergamo. The charming city is actually two towns--Bergamo Alta (high) and Bergamo Bassa (low). Bergamo Alta is a beautiful walled city whose architecture dates back to medieval times. Its Piazza Vecchia, slightly overhauled in the Renaissance, is considered the most beautiful square in Italy. Bergamo Bassa is the more modern city, with architecture from the 19th and 20th century, though it still has some signs of early Renaissance. Bergamo is the gateway to the Swiss Alps.

With a massive apertivo buffet, stop by Storico for the cheapest dinner/drinks combo in town (and delicious, to boot!). For 7 euros, get a cocktail or a glass of wine, and fill your plate as many times as you like from the buffet of warm snacks—focaccia, pizza, pasta dishes, cold salads, and chips are always found on the “menu”! Make sure you sit outside, though, to get the best view of the people milling about in the beautiful Piazza de Ferrari.