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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.

Among vacationers who’ve been coming to Grand Cayman forever, there’s a whole faction that essentially camps out at Rum Point all day every day, and you’ll understand why as soon as you see the place. Tucked away, super low-key, and graced with a ridiculously photogenic pier—its perfectly weathered planks cutting a striking figure against the tranquil, turquoise surroundings—this beach is the ultimate spot for settling into a lounger or hammock between water-sports outings. Rum Point’s namesake booze—which used to wash ashore by the barrel, according to legend—is available in all manner of cocktails here, of course. But order at least one mudslide at its spiritual birthplace: the beach’s beloved Wreck Bar.

Join throngs of locals on the five-minute ferry ride across Victoria Harbour between the Tsim Sha Tsui cruise pier in Kowloon, on the mainland side, and the Central Pier on Hong Kong Island (a slightly longer ride goes to Wan Chai on Hong Kong Island). This is not just any ferry: The historic green and white Star Ferries have been moving the masses back and forth for decades, with the origins of the company going back to 1880 with the service of a single steamboat, the Morning Star. Today, the classic wooden boats make the trip many times daily, and a ride provides a great view of the city’s famous skyline and a whiff of nostalgia to boot.

While Cape Point is not, in fact, the southernmost tip of Africa—as is often claimed—it is generally accepted that the Indian and Atlantic oceans meet somewhere between here and the real tip, Cape Agulhas. Still, Cape Point is about as dramatic as you can get, with the land falling steeply away on three sides, the wind whipping around the cliffs, and the ocean churning below. The road to the point, at the end of a drive from Cape Town, goes through 20 miles of nature reserve full of baboons and antelopes. For those who don’t want to walk up to the lighthouse, there is a funicular, but to reach the point itself, you’re going to have to hike.

There’s no better place than Vancouver to try a Vancouver cocktail, it’s the perfect pre-dinner sharpener, although it works rather well as an after-dinner treat too. It’s said to have been created at the Sylvia Hotel down on English Bay in the 1950s and its fans included Errol Flynn. It’s a riff on the Martinez, made of gin, Benedictine, sweet Vermouth and orange bitters. Although the Sylvia is, of course, the most authentic place to try it, I have to recommend you make for the all-weather patio at Cin Cin to sip bartender David Wolowidnyk’s version which is smooth, delicious, and really far too good to just have one...

Baseball had nothing to do with the naming of Fenway Park: The stadium gets its moniker from the nearby Back Bay Fens, a stretch of saltwater marsh in the heart of Boston that was landscaped into a park by Frederick Law Olmsted. The Fens are among the wilder parts of the Emerald Necklace, 1,100 acres of parklands running from the Charles River to Brookline that include familiar spaces like the Boston Common and Boston Public Garden but also less-traveled (by visitors, anyway) sections like Olmsted Park, Jamaica Pond, the Arnold Arboretum, and Franklin Park. The arboretum, part of Harvard University and established in 1872, is one of Olmsted’s most unaltered terrains, with paths running up and around 261 acres of woodland interspersed with a curated collection of trees, plants, shrubs, and vines native to New England.

Mile-long Newbury Street, lined with handsome 19th-century brownstone homes, is synonymous with shopping in Boston; it’s also the place to go to get your hair done up nice. Between Arlington Street and Massachusetts Avenue you’ll find an eclectic mix of boutique and designer shops, hair salons, art galleries, and restaurants that generally skews upscale (Tiffany’s, Chanel, Dolce & Gabbana) but also includes the original location of the Newbury Comics record store and a T.J. Maxx. Eminently strollable and dotted with sidewalk cafés, Newbury Street is the hip heart of the Back Bay neighborhood, perfectly distilled at eye-candy drinks-and-dining hot spots like Sonsie and Stephanie’s on Newbury.

Junkanoo is one of the Bahamas’ most colorful traditions, a more than 200-year-old street celebration and parade, like Carnival with a Bahamian twist. It takes place during the Christmas and New Year’s holidays. But visitors can learn about Junkanoo any time of year with a stop at the Educulture Junkanoo Museum on West Street in downtown Nassau. The museum’s exhibits highlight the history of the celebration, along with examples of the elaborate costumes, music, and dances that take place during the events. There’s also an interactive element, with visitors invited to make masks and learn how to dance to Bahamian music. The Educulture Junkanoo Museum is open weekdays from 9 a.m. to 5 p.m.

As a rule, Bermuda’s sense of sophistication includes a certain level of old-school formality. With the opening of this namesake eatery from the internationally renowned and somewhat hipster chef Marcus Samuelsson, the island’s approach to haute cuisine has taken a chic turn. Housed in the Hamilton Princess hotel with its landmark pink facade, the restaurant boasts a vibe that’s contemporary and airy with an emphasis on the turquoise sea. All tables have excellent views of Hamilton’s harbor, and the menu is—as might be expected—seafood-heavy, with dishes like Oysters with Black Rum Mignonette and grilled salmon. The local catch of the day and island-grown onions, along with other dishes, are prepared on a wood-fired grill that’s visible from the dining space.

This casual creperie-bistro sits on Rue Saint-Jean, one of Québec City’s busiest shopping streets. With its brick walls and fireplace, the Breton-owned restaurant has a cozy and casual feel. It’s best known for buckwheat crepes, a favorite typical dish of Brittany, but whether you like your crepes savory or sweet, you’ll find something on the menu to satisfy you. There are traditional fillings like cheese and mushrooms as well as shrimp, salmon, and, this being Québec, maple syrup.

Started by a British master weaver almost 20 years ago, Mungo weaves a wide range of quality linens, throws, blankets, bedding, towels, and apparel, which are sold internationally. The company says that ethical trading and integrity underpin its philosophy, and it is particular about sourcing quality natural fibers. The linen in raw form comes from Belgium, while the cotton, mohair, and wool are from South Africa. You can view some of Mungo’s weaving on its 19th-century Hattersley looms at its Old Nick Village headquarters, outside Plettenberg Bay. Better yet, just go to the Cape Town store (with its own micromill) on Hout Street and see the products for yourself.

Kananaskis Country is a stunning wilderness area that lies just outside of Canmore, Alberta. The region borders Banff National Park and the scenery rivals it’s famous neighbour. The key benefit to outdoor fun in Kananaskis Country is the complete lack of crowds! It might be near Banff, but it feels a world away. Hiking trails, bike paths, and beautiful lakes abound and it’s quite common to have them all to yourself even during the busiest summer weekends! Check out the Upper and Lower Kananaskis Lakes at sunset, as it’s a prime location near the Continental Divide that offers stunning evening light.

North Star Pinball (or North Star Machines à Piastres, if you were wondering how to say pinball machine in French) is pretty much what you would expect from its name, a bar with a collection of about two dozen vintage pinball machines, most dating from the 1960s to the 1990s. There’s a long list of beers in bottles and on tap, cocktails (including seasonal specials), housemade ginger beer, and a short menu of bar snacks—pickled eggs, pepperoni, mixed nuts. Right on “the Main,” as locals refer to boulevard St-Laurent, the bar draws a loyal group of regulars who appreciate this no-attitude place.

A little beyond the city walls, and just a few blocks from the Musée National des Beaux-Arts de Québec and the Plains of Abraham, Avenue Cartier offers a different shopping experience than what you’ll find in Old Town. This is a part of the city more popular with locals than tourists, and instead of shops selling sweatshirts with moose and maple-leaf designs, you’ll find upscale stores and boutiques. The street is also known for its dining and nightlife options, offering a wide selection of restaurants, pubs, and bars where you can take a break from the hard work of shopping.

The most stylish spot in Fort Myers’ River District, Firestone occupies a historic, four-story building right on the water. In the restaurant, guests enjoy steak and seafood specialties paired with fresh, local produce. Also onsite is the rooftop Skybar, open daily from 4 p.m. for sweeping views of the Caloosahatchee River and Downtown River Basin, as well as a special martini bar, which welcomes patrons on Friday and Saturday nights.