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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!

The centerpiece of Turks and Caicos is Grace Bay, on the island of Providenciales (known locally as Provo), where the miles-long sugar-sand shore routinely tops “best beach” lists for the Caribbean and the world. The inland area along this stretch of northern shoreline is where you’ll find most of Provo’s hotels, shopping, and restaurants. Grace Bay is part of the Princess Alexandra National Park. It has calm waters and a sandy seafloor with no rocks or corals to step on, making Grace Bay the perfect place for swimming, splashing along the shoreline, parasailing, and stand-up paddleboarding.

Mandarin Oriental’s first Caribbean resort has all the amenities you’d expect from the luxury brand—with the price tag to match. Nestled within lush greenery overlooking the white sands of Godahl Beach, the 26 suites and villas, which sit on the grounds of a 1,200-acre estate on the island of Canouan, are elegantly appointed with modern furnishings, marble baths, and rosy accents befitting the hotel’s name. Here, though, it’s all about the public spaces, including a Jim Fazio–designed golf course overlooking sparkling blue waters, a hilltop spa specializing in island-themed treatments, and four elegant restaurants serving every kind of cuisine, from pan-Asian to Italian. At Turtles, a cocktail lounge straight out of the Hamptons, opt for the Pepper Bliss, made with rum, bell pepper syrup, and pineapple juice.

First domesticated on this tiny island in 1840, the aloe plant is so important to Aruba that its image is emblazoned on the nation’s crest. Crops once extended over nearly two-thirds of the island and, to this day, remain Aruba’s largest export, explaining why the plant is a frequent motif in local art and architecture. For more information, visit the Aruba Aloe Factory, where you take a guided tour and learn about the manufacturing process. Then, head to the museum to browse a small collection of ancient aloe planting tools as well as books on the plant and its history.

One of my favorite places in the whole world—Vieques! I’m actually a little apprehensive to share, because I’d love to keep it the semi-secret it is. If you time it well, you can have this beach all to yourself.

From the moment you touch down on the grounds of the 135-acre working cocoa farm, a stay at the Fond Doux feels like a step back in time. It begins in your suite, one of 15 cottages that have been lovingly restored by owners Lyton and Eroline Lamontagne in the colonial style, with traditional gingerbread trim, four-poster beds, and pastel walls. Though some cottages have private plunge pools, you’ll want to make your way to the cascading main pool, which overlooks a verdant rain-forest glen. If all this sounds a little sleepy, don’t fret: A free shuttle is available to whisk guests to nearby Sugar Beach, and frequently rotating minibuses pass the hotel on their way to restaurants and shops 10 minutes away in Soufrière.

Wide, sandy Cane Bay Beach, on St. Croix, has a lot going in its favor: The medium-size surf, full-service dive shop, barbecue grills, and fun sites to snorkel make the beach popular with families, kids, and even dogs. Choose simply to rent some beach chairs and bask in the warm Caribbean sun, or opt for a game of beach volleyball or a swim in the clear waters.

This small, undeveloped beach with views to St. Kitts is for couples, not kids. Located down a short path from the highway, the beach has an unspoken rule to come back later if you see another car parked on the shoulder—sort of the Nevis version of the towel on the doorknob. Not only does this system preserve privacy, it helps ensure that Lovers Beach remains one of the most secluded spots in the Caribbean.

A narrow strip of land divides the northern Atlantic and southern Caribbean sides of Frigate Bay, making it easy to walk from one section to the other. Many visitors do just that, as hotels like the St. Kitts Marriott Resort and Sugar Bay Club are on the north side, while the beach bars of The Strip sit on the south side. The sand and scenery around the resorts is better, but the nightlife on South Frigate Bay is among the island’s best.

This woman-owned artisanal aged-cheese producer was on the front wave of what is an increasingly vibrant local food movement. Wanda Otero, a microbiologist, decided to start her business in part to offer Puerto Ricans an alternative to expensive imported cheeses. She has since expanded into yogurt-making, and her products are now sold in supermarkets and found on the menus of the island’s finest restaurants. Travelers can visit the Vaca Negra facility for a tour, which includes the opportunity to make their own cheese.

The 1905 Cadillac sparkling under the bright lights really commands the attention of the room. This hot ride, in the center of the Cayman Motor Museum, is the exact model of the first car ever driven on the island. Browse through more than 55 classic and exotic vehicles as well as 18 various vintage motorcycles. This museum displays rare and one of a kind automobiles and isn’t just for motor enthusiasts. Cars like the original Batmobile used in the 1960’s television series of Batman as well as Elton John’s Rolls Royce make this museum a must-see.

My sister freaked out when she heard that Kenny Chesney would be playing a special concert at the Atlantis Resort on Memorial Day weekend last year. She begged me to go, and with neither of us having been to the Bahamas, it was an absolutely fabulous experience. We shopped and laid out by the pool during the days, while experiencing all the nightlife and restaurants that the resort has to offer. We had a great weekend, and Kenny was the topping on the cake!