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One of Cancún’s oldest restaurants, La Habichuela was a 1970s original whose owner wanted a place to hang out with friends. It’s become an upscale dining room featuring local Mayan recipes alongside Mexican-Caribbean fare. The now iconic restaurant borders downtown’s Las Palapas Park, and has a charming backyard garden adorned with twinkly lights and climbing vines. Start the evening with balché, an ancestral Mayan drink made from the bark and roots of the balché tree that have been soaked in honey and water. For your entrée, try the amaranth fish bathed in flavorful tamarind and mango vinaigrettes.

Owners Bryan Lewis and Eric Gaspard recently opened the Twisted Cork Café, a wine-focused restaurant located in the historic Frenchtown district of Charlotte Amalie. The neighborhood, which is busy with cruise passengers during the day, slows down to a more mellow island speed in the evenings. Daily specials, which often feature just-caught fish and produce from an on-site garden, are recommended.

As glassy high-rises sprout up on the site of a former gasworks complex on the Amstel River, this early-20th-century red-brick house, where the factory’s director once lived, has been preserved and turned into a smart café and art space. All rooms in the two-story home have been outfitted with mod, vintage furnishings and rotating artwork from area artists, and you’re free to grab a drink or coffee at the bar and enjoy them wherever you wish. The riverfront terrace is the perfect spot for a coffee and a bite; the menu includes sandwiches and goods baked on-site using locally sourced ingredients. Arrive early for a table for the busy Sunday brunch, which occasionally features live music.

Founded in 1838, Amsterdam’s zoo, just east of the Canal Ring, is one of the oldest in Europe, with a parklike setting that also houses an aquarium and planetarium (entrance to both is included in the price of admission). The grounds, while not large, are home to around 700 species, including giraffes, gorillas, penguins, pelicans, sloths, and reindeer. A highlight is Lemur Island, where the freely roaming long-tailed creatures scurry and hop all around you. The zoo also recently updated its Asian elephant and jaguar enclosures. The aquarium, which dates from 1882, was fully renovated in 1997 and counts tropical fish, sharks, and sea horses among its residents; it also boasts an underwater scene of a typical Amsterdam canal, complete with a sunken bicycle.

Hop on the free ferry from the city’s Central Station for the 15-minute ride to the NDSM wharf, an old shipyard that’s transformed into a hipster haven with restaurants, bars, and artists’ studios. The waterfront “beach bar” Pllek is a popular spot here; built out of old shipping containers, the soaring, dual-level space has an industrial vibe, with corrugated-metal walls warmed by bright artwork, an indoor fireplace, and huge windows looking out over the IJ River. But it’s the man-made beach that draws crowds in warm weather, with comfy beanbags and loungers where you can while away the afternoon. There’s a nice selection of beer and wine; the food is simple but surprisingly good, and it’s crafted with fresh, organic ingredients. Pllek also hosts live-music events, DJs, dance parties, films, and morning yoga classes.

A 600-suite hotel within a hotel, The Cove is the most luxurious of the room towers at the Atlantis Paradise Island Resort. Kids aren’t banned, but the vibe is definitely grown-up—witness the adults-only Cove Pool, with its DJ-driven party scene, outdoor gaming tables, and mating-ritual pool wear. But there’s a sense of sophistication in the two-story lobby, which soars above ponds of water lilies, as well as the suites, which have balconies with ocean views, sunken living rooms, and marble-floored bathrooms. All the activities of Atlantis, including those that make adults feel young again—such as the Abyss and Leap of Faith waterslides, or the dolphin encounters—are only steps or a free shuttle ride away. Also available is immersive programming that connects guests to the rich history, art, people, food, and festivities of the islands, from exhibits showcasing regional artists and a weekly Junkanoo Fest & Feast (honoring a more than 500-year-old tradition) to five new outposts of beloved local Bahamian restaurants.

One of Caye Caulker’s best beach bars is also its friendliest. Set right on the Split—a narrow channel dividing the island’s north and south portions—Caye Caulker’s most social corner invites tourists and locals to gather for a swim off an extended dock, or to enjoy a cocktail and music. Lazy Lizard’s recently upgraded look includes a variety of umbrella-covered wooden picnic tables, seating under palapas, and a new beach extension with steps leading into the shallow sea areas for easy entry. On the menu, you’ll find typical bar bites: burgers, fish tacos, and full meals like a lobster plate. The bar holds occasional full-moon parties, live music, family-fun days, and beach volleyball tournaments.

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.

“For those folks who enjoy camping, Hix is the Four Seasons. And for those who stay only at the Four Seasons, at Hix they will think they are camping.” So goes the saying of the owners of Hix Island House, located on remote and beautiful Vieques Island. Puerto Rico’s first sustainable lodging facility, the hotel caters to guests who know that going green and living luxuriously are not mutually exclusive. Rooms come with See Design bedding as well as Frette robes and towels. Solar panels provide power, and wastewater from each room supplies the lush gardens. Canadian architect John Hix is responsible for the hotel’s striking concrete exterior, which stands in stark contrast to the surrounding hills, yet provides guests with both privacy and sweeping views out to sea.

Blending a cheerful, laid-back spirit with a splash of formal elegance, The Reefs Resort & Club is uniquely Bermudian. Staff greets you with a rum swizzle upon arrival at the family-owned and operated property, then whisks you up to a room where bright botanical prints complement crisp white linens, deep wood tones, and tile floors, and windows offer views of the Atlantic’s turquoise-tinged waves. Days are spent indulging in frangipani salt scrubs and ayurvedic massages at the spa, sitting in on a sunrise yoga session on the beach and hitting the links nearby, or simply napping on a chaise at the freshwater infinity pool. Sited to capture awe-inspiring vistas of the water, limestone cliffs, and lush vegetation that surround the resort, three restaurants serve classic continental fare, but more adventurous types can rent a scooter across the street to sample the local food scene on a culinary tour of Hamilton and St. George.

This funky spot stands out among Amsterdam’s many urban “beach bars.” You can laze away a sunny afternoon at one of the picnic tables or chairs set up on a wide stretch of sand. Cocktails and beer slake your thirst, while decent pulled-pork tacos, burgers, and poke bowls keep hunger at bay. If the weather isn’t agreeable, the café—located inside a converted warehouse—strikes all the right hipster notes: Think distressed, graffitied concrete walls; leather sofas; vintage television sets; and groovy lighting. An adjacent warehouse hosts all sorts of events, from flea markets to film screenings to dance parties.

Experience fine dining in a tropical outdoor setting at Coco Bistro, one of the top restaurants on Providenciales. Not only is the dining room set among the largest palm grove on the island, but also the chef is known for artfully blending island flavors with continental ones. Entrées may include homemade conch ravioli or jerk pork tenderloin with sweet potatoes and hot pepper honey. You can also pick up a copy of The Coco Bistro Cookbook to replicate your favorite restaurant dish at home.

A recent addition to the Puerto Rican capital’s culinary scene are food hall–style spots where diners can choose among multiple kiosks, or stalls, each featuring a distinct kind of cuisine. Lote 23 is one such spot, located in the working-class neighborhood of Santurce. More than a dozen food entrepreneurs have fare on offer here, from pizza and tacos to bao and burgers. If you just need something to cool yourself off in the tropical heat, there are popsicles and cocktails, too. The alfresco eating area has plenty of picnic tables where you can sit and enjoy whatever you’ve ordered.

This collection of 5,000-plus bags, purses, and accessories—the largest in the world—spans more than 500 years, from a practical 16th-century goatskin money pouch to a whimsical shoe-shaped purse by contemporary Dutch footwear designer Jan Jansen. Displayed beautifully throughout a grand 17th-century canal house and arranged by time period, the collection includes rare French silk bridal bags from the 1800s, delicate art deco beaded purses, chic 1970s Lucite clutches, and contemporary handbags by luxury brands like Louis Vuitton, Mulberry, Gucci, and Prada. Items owned by the rich and famous are here as well: a Versace evening bag Madonna carried at the Evita premiere; the cat-shaped “Socks” clutch that Judith Leiber designed for Hillary Clinton; and Margaret Thatcher’s iconic gray Asprey handbag, which she referred to as her “weapon.” Don’t miss the café’s renowned afternoon tea, with sweet and savory bites served in the museum’s period rooms.

Old San Juan may look, at first glance, like a few other charming cities built during the height of Spanish colonialism—Havana or Santo Domingo, for example—but what sets it apart is the extent to which its architectural infrastructure from that era remains visible. It’s the only city that has its original colonial wall almost entirely intact, and both of its principal forts are in excellent condition, remain accessible to the public, and offer panoramic views of the Atlantic Ocean (so bring your camera). Both El Morro and Fuerte San Cristobal are run by the National Park Service; guided tours will leave you with greater knowledge about the era, as well as the forts’ construction and their role in Puerto Rican history. (There are other, smaller forts in and around the capital, next to the Caribe Hilton, and in Luís Muñoz Rivera Park, plus Fort San Juan de la Crúz in the nearby town of Cataño.)