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For a taste of the good life, head to South Beach, known for its Art Deco hotels lining Ocean Drive and Collins Avenue, glittering nightlife, and see-and-be-seen vibe. The long stretch of beach, starting with the pier at the top of historic Washington Avenue, is a great place to take in the Miami of postcards and enjoy the sunset over the cityscape. This is where you’ll find some of Miami’s best shopping, top-tier nightlife, and award-winning restaurants, not to mention great people-watching and luxury-car spotting.

Go for the scene, not the food, and enjoy the Art Deco décor and great people-watching at this buzzy Left Bank landmark. Despite a limited menu and steep prices, the place is packed day and night. Order a chocolat chaud and sit on the terrace, watching the world go by.

Parque de los Novios, in the center of Santa Marta’s colonial sector, is perfect for people-watching in the late afternoons when the tropical heat abates. Everyone from the gentry to the common folk—not to mention a plethora of brides posing beneath the gazebo—seems to treat themselves to a nice stroll around the park. Nearby restaurants and bars come alive after night falls, as do, of course, street artists and musicians.

With its medieval churches and soft rolling hills covered by vineyards, Kakheti is Georgia’s answer to Tuscany. Among the region’s most charming places to stay is Chateau Mere, located near Telavi, the largest city in Kakheti. The place calls itself a chateau, but the quaint, turreted, rough-hewn stone complex feels slightly like a ramshackle estate of an eccentric, over-hospitable uncle who treats hotel guests like friends. Owner George Piradashvili is gregarious (even by Georgian standards) and is the entrepreneur behind the excellent Winiveria winery. He opened the hotel in 2011 because he wanted a place for his friends, who are mostly Georgian musicians and actors, to stay in. The living room is crammed with photos of Georgian celebrities who usually stay here, along with a piano, antlers galore, Georgian textiles, and an antique gramophone that all create a homey feel. The 15 guestrooms have pine floors and tasteful, minimal furnishings. Most guests prefer to hang out by the pool or on the terrace, taking in the romantic views of the lush Alazani Valley and the dramatic Caucuses mountains beyond, drinking the owner’s juicy Saperavi wines or the aromatic white Khikhvi, and tasting his house-cured meats and stringy, briny artisanal cheeses. The hotel also arranges grape-picking and crushing activities, cheese-making and bread-baking demos, and horse riding. Piradashvili also owns the romantic lakeside Royal Batoni hotel.

Vice Versa is the best of many worlds. It serves Western fare by day as a cafe and restaurant, and at night it morphs into an underground bar serving cocktails and local and foreign beers. The bar also hosts a variety of bands for intimate live music nights. Frequented by both locals and expats, Vice Versa also has a stellar rooftop space for those sunny days and breezy nights. Still not enough? There’s also a skate shop run by pro skater Xiao Jian on the premises.

From the 16th to the 19th century, drovers were the men responsible for leading cattle out of the rugged Highlands to the markets in nearby towns and cities. Today, they serve as the inspiration for the Drovers Inn, a hotel and pub just north of Loch Lomond. Nestled near the banks of the River Falloch, the property offers a rustic setting for filling meals, frosty pints, and drams of malt whisky. Come for bar-food favorites like steak-and-Guinness pie, fish-and-chips, and venison casserole, and stay for the live musical acts that play every weekend. As the inn has been in operation for some 300 years, tales of various hauntings are part of its appeal.

After Toronto, Montréal is the Canadian city with the largest population of residents of Italian descent. For more than a century, the community has been centered in one of the city’s most charming neighborhoods, Little Italy. The way to the heart of this neighborhood is arguably through its stomach or, rather, the Jean-Talon Market, where residents have come to buy produce and stock their pantries since 1933. Even if you aren’t shopping for fresh vegetables or fruits, it’s a good place to come to sample Québecois products and buy gifts like local jams, jellies, and maple products to take back home.

Set on Cox Bay, one of the best surf spots in Canada, the Pacific Sands resort offers one- bedroom suites and two-story beach houses with fireplaces and bay-view patios. If you forgot your raincoat or rubber boots (two must-haves in Tofino, which receives 100 inches of rain per year), don’t worry. The resort stocks them in every room. From $144. (250) 725-3322. This appeared in the August/September 2013 issue.

Volunteer Park is a beloved neighborhood park in the heart of Seattle’s Capitol Hill. Originally created in 1876, the park was named in 1901 to honor the volunteers of the Spanish-American War. The Seattle Asian Art Museum is located inside the park, as well as the Volunteer Park Conservatory, which features 600 varieties of orchids and a cactus house. Take in a stunning 360-degree view atop the historic water tower, or stroll the walking paths around the reservoir.

Tucked on the corner of Hopkins Avenue and Monarch Street, White House Tavern occupies one of Aspen’s oldest buildings, a small Carpenter Gothic–style white house that was built in 1883. The offerings here don’t change from when the restaurant opens for lunch at 11 a.m. to when the sky darkens and the cocktails start flowing into the night. The menu is made up mostly of hearty salads (Thai steak and noodle, kale with rotisserie chicken) and tasty sandwiches, including an incredibly crispy chicken sandwich and a flavorful, perfectly cooked prime rib au jus piled high on a homemade roll. The cocktail list is short and tends toward the classics—negroni, margarita, martini—but the wine list is surprisingly ambitious.

Austrian wines are made all the better by a visit to the many vineyards and wine taverns (Heuriger) on the outskirts of Vienna. Wieninger vineyard is located north of the city on the Nussberg. A light meal and wine outdoors among the vineyards is a great way to cap off an evening in Vienna. Trams run from the city center to Nussdorf. To explore more heuriger, the little Vienna Heurigen Express train runs from Nussdorf to Kahlenberg and Grinzing.

Bray Farm is located in Yarmouth Port, Mass on Cape Cod. There are some scenic walking trails there and a variety of animals. Just behind the farm is a nice Cape Cod marshy area. If you go there during mealtime the animals can get animated. These sheep were too busy eating to care that I was taking a picture of their backsides; Either that or they were in time out.

This acclaimed ice cream parlor with more than 15 locations (most Santiago malls have one) dishes out every imaginable flavor. Regulars crave dulce de leche, lifted from the namesake caramel dessert. Or try the Chilean classic called café helado, a tall glass of strong, chilled coffee with a scoop of ice cream at the bottom and whipped cream on top. ¡Ay, yi, yi! A rare spot for decaf coffee, as well as sugar-free and gluten-free treats, La Rosa serves breakfast, lunch, and high tea.

Rooftop pizza restaurant Mambo Italia is a great place to go with friends or to listen to the live music regularly playing here. There’s a covered indoor area with colourful chairs and mismatched tables in case the weather turns, but on a sunny evening grab an al-fresco table and watch the traffic streaming by below. Best items on the menu are, of course, the pizzas. There’s a creative range of options the team here have dreamt up, or you can simply create your own.

Part concert, part traditional resort show, The Spazmatics are a throwback to the 80s. The band members, each of whom has a dorky on-stage persona, play a myriad of popular songs from this decade of dance hits ranging from hip-hop highlights to pop classics. This is a long show, spanning several hours with an intermission in the middle. Audience members are encouraged to get up and dance the night away to music that we all so fondly remember from yesteryear.