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Hotel Nacional de Cuba wasn’t built to look historic; it is historic. Since its doors opened in 1930, the grandiose lobby has been a hub of activity, and nowadays the buildings well-preserved interiors offer an authentic glimpse back in time. The hotels halls have been walked by some of the most notable international figures of the past century; from Ernest Hemingway and Frank Sinatra to Vladimir Putin and John Kerry (though, separately). For a classically Cuban experience, treat yourself to a room that overlooks the waterfront, grab a drink at one of the property’s six bars, and watch the sun set as colorful jalopies zoom by on the Malecón.

Ybor City can boast that it is home to the oldest continuously operating restaurant in Florida. The Columbia Restaurant opened in 1905 as a café serving coffee and Cuban sandwiches to local cigar workers. Today, the original family continues to run the eatery, and while it now has a much larger menu, the Cuban sandwiches remain a favorite.

Don’t be confused by the name: This isn’t street food so much as dockside warehouse food. Walk over Inderhavnsbroen, one of the city’s newer bridges (opened in 2016), and you’ll cross from the heart of Copenhagen to a former industrial area that is now a foodie paradise. It is to the city what Borough Market is to London—a hugely popular attraction where people flock to eat great food off paper plates. Chinese, Korean, Italian, Moroccan . . . It’s all here and so inviting that it’s hard to know where to start. The only note of caution: Copenhagen Street Food is so popular that the weekend crowds can be intimidating.

Hogfish Bar and Grill, under a thatched palapa roof with open sides, is tucked in among the boats and gulls of Safe Harbour Marina in Stock Island. In short, a meal or a drink there makes you feel like an insider, a salty local far from the crowds downtown. That in-crowd feeling is burnished on weekends, when local bands play sets, or during one of the events held by Hogfish during the season, like shrimp boils. The simple food is served generously on plates crowded with side dishes. The hogfish sandwich, served fried on Cuban bread, is the stuff of late-night-post-beer legend.

This three-mile stretch of white sand is the only public beach at the gated Puntacana Resort & Club. Even so, non-guests can only reach the beach after dining at the resort’s oceanfront Playa Blanca Restaurant. It’s worth it, though, as the calm turquoise water is ideal for swimming, kayaking, and catamaran sailing. A mesh barrier keeps seaweed out of the swimming and beach areas, ensuring pristine water and sand as far as the eye can see.

For those who aspire to travel as trendsetters in Jamaica, it helps to know that Port Antonio, way out on the eastern end of the island, is the destination to head for. And the address to shelter at is the Trident Hotel, whose 13 waterfront villas would not look out of place on South Beach. Nor would the crowd that hangs around its infinity pool or in its restaurant, Mike’s Supper Club, where local musicians and the occasional celeb sit down to knock out tunes on the 1917 Ferrari-red grand piano. The Trident Castle, a kind of fantasy annex, is a former private residence whose grand rooms, sea-view terraces, and dollhouse-size chapel make it ideal for destination weddings. A hard road to get there? Not for guests who avail themselves of the helicopter pad.

The Hermosa Inn, first opened in 1936, has the kind of history that a cowboy keeps under his hat. With 43 rooms and casitas spread across six acres of Arizona desert in the upscale Phoenix suburb of Paradise Valley, the inn was originally the home and studio of cowboy artist Lon Megargee. A $5.5 million renovation completed in March 2017 updated the hotel for the modern era. It still retains a historic feel, but without the possibility of escape it had when Megargee, a welcoming host clearly uninterested in background checks, built a tunnel from the main building to the stable in case a visit by the sheriff made it necessary for less law-abiding guests to execute a quick getaway. But then, with Camelback Mountain as a backdrop, few guests nowadays are in a hurry to leave.

Mexico City’s fabulous Sundays-only flea market—in a down-at-the-heels neighborhood near the Centro Histórico that looks worse than it is—is a must-do for anyone who loves the nostalgic or the campy. No fewer than six block-long aisles host dozens of stalls featuring all manner of trash and treasure, including antique furniture and light fixtures; frilly housewares that get you back in touch with your inner grandmother; books and vinyl LPs (record players, too); artworks that might be worth a fortune; toys; dolls and action figures; and fantastic vintage beer and soft-drink trays that make great, practical CDMX souvenirs.

No matter what the season, it’s worthwhile to wander through the exquisite Retiro Park when you’re in Madrid. Here you can find a tranquil escape from crowded streets and museums. The unrivaled architecture of Madrid is echoed here in the wonderful monuments, statues, and buildings. Be sure to visit the gorgeous Crystal Palace (Palacio de Cristal), originally a greenhouse and now used for art exhibitions. Look for the beautiful black swans in the lake.

Head to Willemstad’s Pietermaai district at happy hour, and you’ll quickly stumble across a row of festive Euro-style bars on Nieuwestraat—but none are as funky and eclectic as the Cuban-themed Mundo Bizarro. This indoor-outdoor lounge-restaurant is filled with antique furniture, bold paintings on colorful walls—look for the older Cuban woman wielding a cigar and a sassy stare—and knickknacks from around the planet. Try some of the most beloved items from its international menu, such as smoked-beef carpaccio, rib eye, salads, and quiches. Fridays at 10 p.m. are popular for the live salsa band.

One of only two hotels right on Biscayne Bay (the other is the Standard), rooms at Mondrian South Beach are coveted by guests wanting a stellar view. Designed by Dutchman Marcel Wanders, the hotel’s decor is intended to evoke a sense that one is floating around in an underwater world, and the property is described as an homage to Sleeping Beauty’s castle. The slightly whimsical and slightly creepy mermaidlike woman whose face appears on walls throughout the hotel is the “keeper” of this “castle,” where incongruous elements—traditional blue-and-white Dutch porcelain juxtaposed with busy black-and-white patterned wallpaper, say—somehow work in odd, unexpected harmony. Everything about the hotel feels spacious, including oversized rooms, many of which are flooded with sunlight and enjoy bay views.

You don’t have to go far to find fun at Hawks Cay, nor do you have to go far to relax by the water there. The resort, which takes up much of tiny Duck Key, is known for its lagoon, five pools (including one reserved for adults and another featuring a pirate ship slide), and a Dolphin Connection program that offers complimentary viewings and hands-on experiences. Water sports are plentiful as well, with kayaks, paddleboards, and boats to rent, and guests can book fishing trips, scuba and SNUBA diving, and kiteboarding instruction. There’s also a Cliff Drysdale tennis program, a spa and fitness center, and a kids club. The resort closed for one year after Hurricane Irma, reopening in September 2018 after a $50 million renovation to the main hotel, a project that included the redesign of all 177 rooms and suites, as well as the creation of a new upscale steakhouse, a seafood-focused café, and a marketplace with to-go options—these supplement the three poolside grills and cocktail bars. Privately owned two-and three-bedroom homes are also available to rent through the resort.

Key West’s most famous literary resident, Ernest Hemingway, lived in this two-story Spanish-colonial villa for nearly a decade and composed several of his best-known works here. His second wife, Pauline, insisted they add a pool to the spacious grounds—the first inground pool in Key West. The cost ballooned to around $20,000, a fortune in the 1930s, and was said to have contributed to the breakup of their marriage. It’s just one of the fascinating stories guides will share on the half-hour tour of the home and gardens (included in the price of admission). And yes, you’re guaranteed to see plenty of six-toed cats, descendants of Hemingway’s original six-toed cat, Snow White.

Founded in 1984, this is the oldest cigar factory operating in the Florida Keys, and it uses traditional Cuban methods to cure and roll its stogies. You can choose from a large selection of cigars and also watch a skilled torcedor (cigar roller) in action.

Visitors can browse an extensive selection of cigars—ranging from mellow to full-bodied blends—many of which are rolled on-site using premium tobacco sourced from Central America and the Caribbean. One of the highlights of a visit is watching a master torcedor (cigar roller) at work, offering a rare glimpse into the artistry behind every hand-rolled cigar. Whether you’re a seasoned aficionado or a curious first-timer, the factory’s welcoming staff are happy to guide you through the selection process and share insights into the island’s rich cigar-making heritage.

Whistler Blackcomb receives lots of press about its big-mountain features, but the resort offers plenty of terrain for every family member and skill level. The Whistler Blackcomb Snow School, among the best in North America, is great for both seasoned skiers and kids as young as toddlers. Even tweens and teens can enjoy small-group lessons, which offer equal parts socializing and instruction in the terrain parks and beyond. Welcome on the Whistler and Peak 2 Peak gondolas, non-skiers will have the village to themselves during the day. When back with their group, they can hang at one of the more than 25 on-mountain restaurants.