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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.

Even if it weren’t arguably the grandest hotel in all of Prague, you’re simply not going to find a more centrally located address than the five-star Four Seasons. At the foot of the Charles Bridge in medieval Old Town—with views across the Vltava to Prague Castle in one direction and over the Jewish Quarter and Rudolfinum Concert Hall in the other—the 157-room property is, in fact, three distinct historic buildings—one Baroque circa 1568, another Neoclassical from 1827, and the last an 1883 Neo-Renaissance edifice—tied together by a contemporary main building built in 2001. Given a sumptuous makeover by renowned French designer Pierre-Yves Rochon in 2012, the rooms and public spaces feel at once stylishly modern and timelessly refined. Though the neighborhood’s attractions beckon, don’t miss a chance to dine at CottoCrudo, the riverside Mediterranean restaurant and bar that is considered one of the city’s best.

If you grow tired of tasting your way around menus of typical Québecois dishes, Stash Café is an appealing alternative in Old Montréal. This budget-friendly Polish restaurant has the feel of an inviting tavern, with seating in old church pews. The menu consists of Polish favorites: perfectly prepared pierogis, kielbasa, and hearty borscht. If you are in Montréal on a gray winter day, it’s a menu that will warm you up before you bundle up again to continue your sightseeing.

There are 14 outposts of the famed chocolate shop in and around town, but the one to go to is its flagship, which occupies a prime corner perch on Paradeplatz. There are gorgeous displays of Sprungli’s signature sweet, the Luxemburgerli, Lilliputian takes on the macaron; its exquisite line of truffles; and its dense, rich, uniquely shaped Truffe cake—quite possibly the best chocolate cake ever. Don’t miss its gorgeous second-floor café.

If one is going to throw around the word “iconic,” let’s make sure it’s used appropriately. As with Zuni. The awkwardly shaped restaurant—it’s in a narrow storefront with wider spaces on the mezzanine—was opened in 1979 by Billy West. West’s best move was hiring chef Judy Rodgers in 1987. She put in a brick oven—and thus the Zuni roast chicken was born. This dish, more than any other (except perhaps the Caesar salad), defines Zuni. The chicken is roasted in the brick oven and served over a bread salad: greens with chewy bread croutons. Simple, perfectly cooked, and seasonal. Rodgers died in 2013, but the restaurant soldiers on without her. The menu changes with the season and with what the local farms are growing, and will doubtless explain the provenance of your meat. Rodgers, along with her peer across the bay, Alice Waters, pioneered California cooking, and the cooks who have passed through here have gone on to define today’s vibrant restaurant scene.

Surprisingly, great cocktails and an ocean breeze can be hard to find in San Diego, which makes JRDN at the Tower23 Hotel somewhat of an anomaly. It may be a scene—there are bouncers at the door, and the 70-foot-long wave wall would be more at home in Miami—but the wind-protected patio is practically on the boardwalk, offering great views of Crystal Pier and surfers catching waves. On warm evenings, drinks like the cava-based Raspberry Sparkler and the spicy chili-mango margarita make the experience even sweeter. JRDN’s happy hour (Mondays–Fridays, 4 p.m.–6 p.m.) offers discounted beer, wine and sake and coincides with the sunset for much of the year, making it a prime time to score a seat outside.

If you like piña coladas, make a beeline for this overwater outpost on glittering Palm Beach. Situated on a pier, the open-air bar and grill boasts uninterrupted views of the water—as well as Aruba’s spectacular sunsets. Here, breakfast, lunch, and dinner are served alongside an extensive array of chilled beverages, attracting a friendly crowd. There’s live music every day during happy hour and, on Sundays, the Travel Session band plays from 7 to 10 p.m. If you’d rather sing yourself, be there on Saturday, when karaoke starts at 8:30 p.m. While the restaurant definitely has a party-like setting, children are more than welcome and high chairs are available for little ones.

If you happen to be interested in architecture, or even if you are not, the Harry Weese-designed River Cottages located from 357 to 365 North Canal Street in downtown Chicago are something you should see. A native of Illinois, Weese is best known for his modernistic style which also focused on historic preservation. The wonderful River Cottages, a mesmerizing display of glass and steel square and triangular shapes, rests beautifully along the edge of the Chicago river. The ideal vantage point for taking in this architectural masterpiece is being perched on a boat in the river. Find a friend with a boat (challenging), or hop on the any of the numerous architectural boat tours originating from Navy Pier (easy), and make your way to Harry’s cottage.

Lyons Cottage, built in 1925 on the corner of Knuckey Street and the Esplanade, is famous for being the first residence in Darwin built of stone. It originally housed executives from the British Australian Telegraph Company; today it’s a café and gallery run by Aboriginal Bush Traders, a nonprofit community initiative. Visitors can shop for artworks, jewelry, clothing and woven fabrics made by Aboriginal artists and artisans. The garden is a pleasant spot for coffee, tea or lunch under a frangipani tree. The café serves dishes made with indigenous produce, such as bush tomatoes and Kakadu plums. And the building’s history is preserved in a hologram exhibit that tells stories of the Overland Telegraph line, which first linked Australia to the rest of the world in 1872.

Craving a Cuban sandwich, but not quite enough to wait in an hour-long line at Paseo? Just a few doors down is Geo’s Cuban and Creole Cafe, which serves up deliciously messy, meaty sandwiches and other Cuban specialties without the wait. The fluffy tostones come piping hot with garlic aioli and Geo’s spicy Cajun mayo for dipping, and the pan con bistek is stuffed with tender strips of marinated sirloin, sauteed onions, and spicy sauce on Cuban bread. You won’t leave hungry — but just in case, you can buy their house-baked Cuban bread to take with you for snacking on later. Try not to look too smug when you stroll, stuffed and happy, past the line at Paseo on your way out.

You won’t find any mediocre pastries or kitschy mugs at Savaya. Here, it’s all about the coffee. Owner Burc Maruflu hails from Turkey, and his passion for coffee permeates this intimate space — which is just big enough for a long mesquite bar, a few tables, and a bright green roaster. The map painted on the wall and the hanging burlap bags show where the fair-trade organic beans are sourced. They’re roasted at the café daily, and small classes are occasionally held for those who want to learn more. Tucsonans regularly name this place as one of the best spots to get a cup of coffee in the city. In addition to the original Midtown location, there are also Savaya cafés in the Santa Catalina foothills and Dove Mountain.

Lake Matheson is a magical little spot near Fox Glacier. It’s a great place to take a walk at sunset, before enjoying dinner and some local wine at the Matheson Cafe. On a clear day, the reflection in the lake proudly displays all the reasons to be in love with the Westland National Park region of New Zealand, while the rugged peaks of Mount Tasman and Mount Cook rise out of the mountain range. This is glacier country at its best. The lack of wind—the lake is set within the dense rain forest—means Lake Matheson’s surface is calm and still. The reflection photo opportunities have made this lake the most photographed body of water in New Zealand (and that is saying something). The walk around the lake takes about an hour and a half, and you have three viewing platforms offering exceptional perspectives along the way. Hit the trail just before sunset and have a glass of Otago Pinot Noir at the cafe while you watch the sun set over those mountains. The cafe opens at 5:30 p.m. and I’d suggest the mushroom risotto.

The Salt Cellar is perched at the top of Gold Hill in Shaftesbury with sweeping views across the Blackmore Vale. This very picturesque hill is really steep and has been used in films. This is a very popular cafe with locals and sits underneath the town clock in Shaftesbury.When visitors come to look at Gold Hill they often walk by without noticing the cafe. If only they turned around. There are benches outdoors and highly sought after window seats indoors with views to enjoy. And then the food. Delicious locally produced salads, sandwiches, daily specials and coffee and cakes. Worried about the calorific value of any of this food? Just walk up and down that hill a few times.

El Charro sits in a converted set of historic houses & buildings a block off Tucson’s old town district—the same location where it began serving food in 1922. We had lunch here, at a big old wooden table in a warmly decorated dining room. Ask to be seated inside, or else in the garden, if the weather’s amenable. It’s a bit cold and dim in the front of the restaurant. I had an amazing vegetarian burrito, stuffed with roasted veggies, avocado and a green corn tamale. The others went for the excellent chimichangas, reputedly invented here (you can read the story on the menu). The special-brewed beer, an amber, was great, the salsa verde addictive, the decor a great talking point.

Prague is one of Europe’s centers of culture, but it was without a proper contemporary art center for far too long. In 2008 the DOX Centre for Contemporary Art opened, with exhibits of provoking art, educational and cultural events, and a mission to encourage critical reflection and dialogue through the presentation of works that speak to social issues of the day. The 32,000 square foot building, converted from a former factory by architect Ivan Kroupa, is a work of art in itself. And even if you tried to, you can’t miss Gulliver, a wooden zephyr-like airship that appears to have landed on the roof (it is used for literature-focused events.). Back inside, DOX also boasts one of the city’s best design shops and a cafe.