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Giving new life to an old haunt, the Cayman Spirits Company has turned the onetime bar area of the historic Pedro St. James into a rum-centric saloon and café: the Outpost Bar. Go for a tasting, and you’ll try as many as five local rums, one of which—the 1780—is aged and available exclusively on-site. The next most important variety to sample here is the Seven Fathoms, if only so you can say you’ve tasted rum that’s been anchored and aged 42 feet (i.e., seven fathoms) below the Caribbean’s surface. Of course, considering the Outpost’s view—prime, uninterrupted seascape—you could have pretty much any drink in hand and be happy.

Lemon Arbour began as just another one of the many rum shops that can be found all over Barbados, but as its reputation for spectacular local dishes grew, so did the actual shop. Now, Lemon Arbor has become the place to go on Saturdays for an extended lunch of souse, fried pork, and other pork dishes, plus cheap Banks beers and rum. Locals often spend all day Saturday limin and meeting up with friends over good food and inexpensive drinks… And you could too, for a real taste of Bajan culture.

Just 25 minutes from Cancún’s international airport is Belmond Maroma Resort & Spa, surrounded by 200 acres of preserved jungle. Guests here still enjoy direct access to the Caribbean Sea and its powdery, white-sand beach, as well as to a wide variety of physical fitness and wellness activities and services. Rooms are generous in size and are filled with sunlight, let in through large windows. Tile floors and design accents—throw pillows and furniture, for instance—have an earthy color palette. Many rooms feature indigenous artwork and handmade furniture. Though it might be tempting to stay within the confines of the resort, the area is home to a number of worthwhile attractions, including the Maya site of Tulum and a biosphere reserve; the concierge can provide information about both, as well as tips for guided excursions and reputable outfitters.

This open-air hotspot with a colonial flair melds Asian and Caribbean flavors for combos such as shrimp with lemon-tequila sauce and coconut rice and carpaccio of squid with wakame. Order a chilled cocktail (we love the ginger drinks with crushed ice) for a refreshing antidote to the Caribbean heat.

Soaking tubs big enough for two and double walk-in showers provide a clue that this beachfront all-inclusive, located less than 20 minutes from the airport on a peninsula just to the southwest of St. John’s Harbour, encourages families to look elsewhere. And while only the Premium Beachfront Suites have those particular romance-inducing amenities, there are other features, such as hideaway tropical dining, that will convince honeymooners and other couples that they have stepped into their own Gauguin landscape. Hence, the most secluded rooms, each with its own plunge pool, are called the Gauguin Cottages. Even among Antigua’s 365 beaches, Galley Bay’s is a visual standout that is longer and less crowded than most. The ocean here can get too rough for swimming, but the beach seldom fails to please for sunsets. Guests with limitless energy can choose from complimentary activities such as tennis, sailing, and stand-up paddleboarding. Or they can save their energy for honeymooning.

Escape the bustle of the city by ducking into the quiet courtyard garden of Begijnhof. Located just a few minutes on foot from the Koningsplein and the Singel canal, this tranquil oasis dates back at least as far as the 14th century. Look among the row houses around the perimeter to find the city’s oldest home, the Houten Huys, built in 1420. And within the courtyard is the Engelse Kerk, or English Church, first constructed in 1390 and refurbished after a fire 100 years later.

Often called one of the world’s most beautiful beaches, Trunk Bay is a crescent of snow-white sand with a small green islet on the north side of the aquamarine lagoon. Part of the Virgin Islands National Park, Trunk Bay is known for its underwater snorkeling trail. Submerged signs along the trail describe the corals, tropical fish and other marine life found within the bay. Visitors can rent snorkeling gear on the beach, and lifeguards are in attendance.

With its own shuttle flight service from St. Lucia and Barbados and an unbeatable location on one of the Caribbean’s most picturesque stretches of sand, Bequia Beach Hotel is an island unto itself. The 10-acre property, easily Bequia’s most luxurious, also includes a spa, two swimming pools, two restaurants, and a canvas-tented bar on nearby Princess Margaret Beach, plus 56 individually appointed rooms and suites furnished in an eclectic, island-chic style (think red four-poster beds, wicker armchairs, and palm-accented throw pillows). Adventurous types can take advantage of the hotel’s free sports equipment (including kayaks, paddleboards, and bikes), while those who prefer more subdued activities can opt for complimentary yoga classes.

While not as large as other ancient Mayan cities in the region, Tulum draws in visitors for its stunning setting of centuries-old temples perched on a cliff by the Caribbean Sea. You’ll pass a large market with souvenirs, a casual Mexican restaurant, and even a Starbucks before reaching the entrance, where a train can take you to the site if you’re not up for the 10-minute walk. It’s advisable to hire a guide to fully understand each structure’s significance and the history behind the ruins; informative signage is all but nonexistent. Don’t forget to bring your swimsuit, as the site encompasses a white-sand beach with soothing waves and beautiful rock formations that’s reached by a long wooden staircase.

Island chic meets urban cool at the Caribbean’s first Park Hyatt, a welcome addition to Banana Bay’s powdery shores. With floor-to-ceiling windows, Scandi-mod furnishings, and freestanding tubs (that come with trendy Le Labo toiletries), the 126 luxe rooms and suites are hard to leave. However, you won’t want to miss the adults-only infinity pool or the on-site Miraval spa, which incorporates local flora into treatments like the soothing aloe-and-lavender body wrap. Also on offer are kid-friendly activities like rock climbing and storytelling with a local historian, making the Park Hyatt perfect for couples and families alike.

Fans of organic skin care make a beeline to this shop for its all-natural, St. Croix products. Ultrahydrating lotions are made with 100 percent aloe vera juice and packed with avocado and jojoba oil. Bar soaps are spiced with Caribbean scents. (The shop just opened a second outlet on the eastern part of the island, across from Government House. )

Old San Juan offers historically and culturally significant experiences including a walk through 500-year-old forts, visits to UNESCO sites, historic churches, museums, the second oldest cathedral in the Americas and Ponce de Leon’s mansion. Cobblestone streets and pastel buildings are perfect for exploration during the day and variety of restaurants and shops make for a complementary evening.

All across Antigua you can find what may, at first glance, appear to be regular pineapples, but if you pass up on sampling the Antigua Black Pineapples, or just Antigua Blacks for short, you’d be missing what many call the sweetest pineapple on the planet. It’s said that Arawak Indians brought the first pineapples to Antigua’s shores more than 1,000 years ago. Upon cultivation in the island’s unique environment, these early pineapples soon adopted the distinctive flavor, appearance, and make-up of the Antigua Black we know today. The flavor being crisply sweet, not cloying, thanks in part to the Antigua Black’s low acidity. The appearance is so diminutive that you may think these pygmy pineapples aren’t ready for primetime compared to their oversized cousins from Hawaii, but one taste and you’ll change your tune. Check out Cades Bay Agricultural Station down south on Old Road to learn the history and explore the Antigua Black’s cultivation first hand.

This is it. The moment you arrive on-island, do not pass go, do not collect $200 — just get yourself to the La Reine Chicken Shack to immediately immerse yourself in the uniquely local St. Croix vibe. No, this is not haute cuisine, this isn’t even a nice looking place, but what it is is an institution sporting the best BBQ chicken on island. Everyone eats here from senators to sanitation workers and all walks of life in between. On Sunday’s you can even expect some roast pork added to the menu. Whatever you order, you won’t go wrong pairing your styrofoam wrapped meal with a nice rum & Coke!

Strolling down Marnixstraat you wouldn’t suspect it’s there, unless you notice a small sign near a stairwell adjacent to the Q-Park. From Nassaukade, there’s no access, but you can see the buzzing venue across Singlegracht canal: Waterkant, a tropical-themed bar and restaurant serving casual fare on the waterfront behind the twin towers of the parking garage. The brainchild of the catering team that brought popular Bukowski Bar, Café Kuijper and Maxwell to Amsterdam, Waterkant debuted to instant success in August 2014. Seemingly overnight, the trio transformed the dilapidated night shelter behind the Q-Park into a canal-side bar and restaurant perfect for a romantic date or evening out with friends. At colorful tables on an expansive terrace, you can watch boats passing by and the Nassaukade street scene over beer, snacks, lunch or dinner. Looking to Amsterdam’s colonial past, the new hotspot features a Suriname-inspired menu with specialties like peanut soup, curried duck spring rolls, fried dumplings and roti roll. If you’re starving, order the Jamaican Jerk ribs—a whopping 16 barbecued bones served with coleslaw and fries. Or blow the budget on a whole Canadian lobster for €25. Wash it all down with traditional Parbo beer or a local craft brew.