One of the northernmost of the Lesser Antilles’ Leeward Islands, this British Overseas Territory consists of the main island of Anguilla (population: 15,000) and smaller islands and cays­—none of which are permanently inhabited.

Popular pastimes mostly take place in the water: diving, snorkeling, sport fishing, windsurfing, kitesurfing, and kayaking. For a less strenuous experience, head to Sandy Island, a small cay accessible by boat.

Anguilla makes up for its lack of conventional visitor attractions with its 33 blindingly white beaches—all open to the public and rarely crowded—and renowned luxury resorts. American designer Kelly Wearstler’s first international project, Four Seasons Resort & Residences Anguilla, thrills with chic interiors featuring natural materials. After a comprehensive, nine-figure renovation closed it down for more than a year, the Belmond Cap Juluca has reopened, offering a plethora of new facilities and guest experiences. Zemi Beach House is an award-winning boutique option on Anguilla’s East End. If price isn’t a concern, consider Altamer, an ultraexclusive resort comprised of three villas on the secluded West End. Guests enjoy 24-hour butler service, personal chefs, in-villa spa treatments, and boat charters to neighboring islands.

For a tiny island, Anguilla punches above its weight, culinarily speaking. Among the 100-plus restaurants, rare is the menu that doesn’t focus on seafood; Anguillan “crayfish” (spotted spiny lobsters) are a must for first-timers. Other local delicacies include tamarind balls, saltfish, johnnycakes—simple quick bread found alongside many meals—and rice with pigeon peas.

Annual highlights include Anguilla Day in May, commemorating the Anguillan Revolution of 1967, and the Anguilla Summer Festival, a 10-day celebration with street parades, dancing, competitions, fairs, and boat races.

With its lush rainforests, waterfalls, and hot springs, this sovereign island nation (population: 168,000) in the Lesser Antilles is a magnet for nature lovers. Adventurers can zipline above the rainforest, and active types challenge themselves with myriad hiking paths, none more famous than the trek up Gros Piton, the taller of the two volcanic peaks that form a UNESCO World Heritage Site. Other key activities: seeing wildly colorful flowers and birds at the Diamond Falls Botanical Gardens, and taking a dip in the famous hot springs at Sulphur Springs. Expect large crowds during the island’s annual Soleil Summer Festival. Highlights include the Saint Lucia Jazz Festival (May) and Carnival (June-July).

Two of the island’s most lauded resorts reside in the shadow of the Pitons. Dramatically carved into a hillside, Jade Mountain is one of the most unusual resorts in all of the Caribbean. It offers jaw-dropping views from its 24 “sanctuaries” (as guest rooms are called), each with its own infinity pool. Sugar Beach, a Viceroy Resort, provides a livelier, more versatile option—guests choose from cottages, villas, bungalows, and residences facing a stunning beach.

Visitors dining off-resort are rewarded with the island’s unique blend of French, African, and West Indian cuisines. Classic Saint Lucian fare includes the national dish of green figs (unripe bananas) and saltfish, lambi (conch), breadfruit, accra (salted cod cakes), rice and peas, and johnnycakes.

Notable beaches are everywhere­—silver- and black-sand beaches in the volcanic southwest, and rugged beaches on the east coast, where endangered leatherback turtles go to nest.

Island-hoppers are drawn to the BVI (population: 32,000), one of the few Caribbean destinations where sailing from island to island is common. This British Overseas Territory consists of the main islands of Anegada, Jost Van Dyke, Tortola, and Virgin Gorda, plus dozens of smaller islands and cays, only a handful of which—most notably the gorgeous Guana Island and Sir Richard Branson’s legendary Necker Island—are inhabited.

The BVI is perfect for sailing novices; well-protected from the Atlantic, the islands are clustered near one another, making it easy to sail from one to the next. Many visitors skip the resorts and spend the night on residential boats or chartered vessels, sailing by day between key attractions. These include The Baths (Virgin Gorda), a beachfront area of unique geologic formations where visitors explore natural tidal pools, tunnels, and scenic grottoes; Flamingo Pond (Anegada), a salt pond where colorful Caribbean flamingos can be viewed; White Bay (Jost Van Dyke), a secluded, popular beach with snorkeling close to shore; and Sage Mountain (Tortola), the islands’ highest point, offering hiking trails through the rainforest.

The BVI offers world-class windsurfing and fishing opportunities, too. Scuba divers tackle one of the Caribbean’s most famous wreck dives, the RMS Rhone, where underwater scenes for the 1977 film The Deep were filmed.

Among the most notable hotels, Guana Island Resort and Scrub Island Resort have both recently reopened after renovations; others, such as Virgin Gorda’s Rosewood Little Dix Bay and Bitter End Yacht Club, are reopening in 2019.

Tortola, the largest and most populated island, is best for those looking to visit historical ruins or experience native culture, which draws upon West African, Creole, and British influences. Popular BVI dishes include regional favorites (johnnycake, peas and rice, saltfish) along with fresh snapper and conch. Epicures visit in November for the annual BVI Food Fête, a collection of food festivals and celebrations.

As one of the largest and most versatile destinations in the Caribbean, the Dominican Republic (population: 11 million) provides a worthy alternative to the smaller, pricier options nearby. The DR, as many call it, shares the island of Hispaniola with Haiti, its western neighbor. Santo Domingo, the bustling capital, delights cultural-minded visitors with its merengue-fueled nightlife and colorful Colonial Zone (a UNESCO World Heritage Site). Other options run the gamut from sleepy beach towns to lively megaresorts.

While the DR has long been lauded for its excellent rum, chocolate, and coffee, young chefs have elevated Dominican cuisine to the point where Santo Domingo—reputedly home to more restaurants than any city in the Caribbean—and the resort hub of Punta Cana offer a variety of fine-dining destinations that wouldn’t be out of place in Miami or Medellín.

There are hundreds of miles of coastline, and adventurers choose among eco-tourism activities spread across national parks, mountain ranges (including Pico Duarte, the tallest mountain in the Caribbean), and rivers. One notable option is Punta Cana’s Indigenous Eyes Ecological Park and Reserve, a pristine nature reserve with freshwater lagoons, lush forest trails, and native animals. And with 26 attractive courses, the country was named the “2019 Golf Destination of the Year for Latin America and the Caribbean” by the International Association of Golf Tour Operators. The DR’s wildly colorful and boisterous Carnival celebration consumes the entire country throughout the month of February, with the biggest parties often taking place on Dominican Independence Day (Feb. 27).

One of the DR’s most famous natives, the late designer Oscar de la Renta, contributed to two resorts: Casa de Campo Resort & Villas (where de la Renta kept a lavish estate), in the popular seaside city of La Romana, and Punta Cana’s Tortuga Bay, where de la Renta designed the interiors. Sanctuary Cap Cana is another big-ticket Punta Cana destination, a Spanish Colonial-style property that’s the country’s most exclusive adults-only resort. More recently, jet-setters have been flocking to the northeast coast for the private Playa Grande Golf and Ocean Club, which includes Amanera, a romantic, Balinese-inspired hideaway that’s part of the Aman Resorts collection.

The Turks and Caicos Islands (TCI) is a British Overseas Territory consisting of the larger Caicos Islands and smaller Turks Islands. A majority of the 31,000 residents live on Providenciales, one of the Caicos Islands.

Having become a trusted, zero-tax option for offshore investors, TCI now boasts one of the fastest-growing economies in the Caribbean. The islands are exceptionally popular with Americans, thanks to the proximity, easy flight connections, and official use of the U.S. dollar.Plus, there are the postcard-perfect beaches and ample water activities (snorkelling tours, boat charters, kayak eco-tours). The islands’ underwater topography and thriving coral reef ecosystem attract expert divers who gawk at sharks, rays, turtles, and dolphins, plus migrating humpback whales.

To most visitors, the islands’ tony resorts and idyllic beaches are the main draw, none more so than Grace Bay. This five-mile stretch of white sand along the northeast coast of Providenciales houses several notable properties, including the Grace Bay Club, an all-suite, all-oceanfront resort—the host site of the annual Caribbean Food and Wine Festival. A few miles away is the first resort on Long Bay Beach, the Shore Club, which opened in 2017 as one of the most anticipated luxury newcomers in all of the Caribbean. Como Parrot Cay, situated on a private 1,000-acre island, offers breezy beachfront villas that are popular with celebrities. Islanders are known as Belongers, and many can trace their heritage back to the African slaves who were brought in to work the islands’ salt pans and cotton plantations. To get a taste of the local culture, seek out authentic dishes—TCI favorites include conch, blue crab, boiled or fried fish, and peas and hominy grits, which are easier to find at casual eateries away from Providenciales.