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Which Caribbean Island Should You Visit?

By Brian Major

Nov 11, 2021

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Each Caribbean island has its own draw, like Anguilla’s long white beaches.

Photo by BlueOrange Studio/Shutterstock

Each Caribbean island has its own draw, like Anguilla’s long white beaches.

Whether you’re looking for adventure, pristine beaches, family fun, or a budget getaway, there’s a perfect destination for your ideal Caribbean vacation.

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The resurgence of travel to the Caribbean is hardly surprising. Despite all the shake-ups in tourism around the globe, the region’s sunny skies, turquoise waters, magnificent natural landscapes, engaging culture, cuisine, and historic sites remain intact and alluring.

Combine these elements with the Caribbean’s extensive air connections to U.S. gateways and the health and safety framework adopted across this tourism-reliant region, and it’s clear that Caribbean destinations will continue to top getaway wish lists.

From families seeking a cost-effective getaway to couples in search of the ultimate romantic getaway, here are the best Caribbean islands to visit based on an array of interests.

Beaches: Anguilla

Anguilla’s greatest treasure may be its magnificent beaches. Virtually all of the 33 found across Cove Bay, Maundays Bay, Rendezvous Bay, and Shoal Bay feature long coastlines, powdery white sands, and deep blue waters. The island’s small-scale character means the beaches are uniformly uncrowded.

Visitors can even take a powerboat trip from Road Bay in the Sandy Ground district to Sandy Island, a small sliver of white-sand beach eight minutes from the shore. The exclusive private island is ideal for an afternoon of easy relaxation sampling barbecue and the tasty local rum punch.

Premium resorts and gourmet dining are standard fare on this British overseas territory in the Caribbean’s Leeward Islands. The big local news is the November debut of the Aurora Anguilla Resort & Golf Club, a beachside luxury resort located on the grounds of the highly regarded former CuisinArt property.

The exclusive new resort delivers three suite categories, a collection of villas offering generous outdoor spaces, and a private jet fleet dedicated for guests’ exclusive use. Boutique property Frangipani Beach Resort and the Four Seasons Resort & Residences both reopened in November. All three are positioned along lengthy stretches of white-sand beachfront with panoramic Caribbean Sea views.

Luxury: Nevis

Encompassing a scant 36 square miles, Nevis offers travelers a fast-disappearing Caribbean experience with no tall buildings, crowds, warehouse stores, or chain restaurants. Its easygoing charm belies an outstanding collection of luxury resorts and high-end dining venues.

A singularly verdant island even by Caribbean standards, Nevis’s green hills surround 3,232 foot-high Nevis Peak at its center. Ruins of colonial-era sugar plantations dot the hillsides, and visitors can explore the landscapes and take in panoramic island views via hiking and ATV excursions.

Luxury resorts are diverse and plentiful here. The 350-acre beachfront Four Seasons Resort Nevis, the island’s largest property, reopened in November following a multi-year, multi-phased enhancement.

The resort features redesigned suites, more than 50 private vacation rental homes, three infinity-edge pools, a Robert Trent Jones II golf course, and a nine-court tennis facility. There are unobstructed Caribbean sunset views at the renovated Mango gourmet restaurant and an extensive collection of the Caribbean’s signature spirit at the Crowned Monkey rum bar.

Built on the site of a 300-year-old sugar plantation, Montpelier Plantation & Beach embraces a laid-back chic with gardens and a private beach equipped with hammocks, cabanas, and a beach bar. The resort’s Mill Privee restaurant serves imaginative, intricate takes on contemporary Caribbean cuisine.

Boutique luxury resort Golden Rock—which has just 11 spacious guest rooms—sits on 100 acres along the slopes of Nevis Peak, amid tropical gardens with views of nearby Antigua and Montserrat.

Locals and visitors alike can enjoy fine seaside seaside at Gin Trap restaurant, but Nevis is also home to casual beach bars, headlined by Sunshine’s Beach Bar and Grill, a stroll across Pinney’s Beach from the Four Seasons.

Water activities—like catamaran sailing, fishing, and diving excursions—are a great way to experience the British Virgin Islands.

Ocean adventure: British Virgin Islands

The British Virgin Islands are a collection of 50-plus islands with diverse landscapes, serene beaches, and green hillsides. The main four are Tortola, Virgin Gorda, Anegada, and Jost Van Dyke, and visitors and residents can journey among them via an extensive system of local ferries.

Not surprisingly, water sports are extremely popular here. Travelers can check the BVI Tourist Board website for links to local operators that lead deep-sea fishing, paddleboarding, snorkeling, and diving excursions. Full- and half-day private boat charters are popular too: Groups traveling on one of Dream Yacht Charter’s catamarans are treated to air-conditioned cabins with a staff including a captain, chef, and first mate.

Best BVI Hotels and Resorts for a Truly Local Stay

The BVI are also home to unique marine sites, most notably the Baths National Park on Virgin Gorda’s north shore. The Baths’ massive granite boulders form sheltered beachfront pools and crevices perfect for exploring, wading, and creating infinite Instagram posts.

Food Fete, the BVI’s premier culinary celebration, returns this year with in-person events across the islands throughout November and December. A highlight will be the Anegada Lobster Festival November 26–28, which includes an island-wide scavenger hunt and tastings focused on Anegada’s spiny lobster, the island’s culinary specialty.

Culture: Puerto Rico

Puerto Rico’s unique heritage combines influences from the Indigenous Taino culture, the island’s centuries as a Spanish colony, and its long stretch as a key port in the transatlantic African slave trade, which profoundly impacted the island’s culture.

“The island’s African legacy manifests itself in all aspects of daily life,” says Dr. María Elba Torres Muñoz, director of the Instituto Interdisciplinario y Multicultural, General Studies Faculty at the University of Puerto Rico. “It is felt and lived in their songs, in the dance, their food, their bodies, their way of speaking, their vocabulary, the way of loving.”

Contemporary visitors can trace Puerto Rico’s African influences through creations on view in seminal collections at the Museo de Arte de Ponce, Museo de las Américas, and Museo de Historia de Caguas, or at the Samuel Lind Studio in San Juan’s colonial district. They can also taste it in dishes such as mofongo, bacalaitos, and pasteles that are based on African cuisine. Try authentic crab-based Puerto Rican cuisine at El Burén de Lula in Loiza, home to Puerto Rico’s largest Black population, a legacy of its 16th-century settlement by Yoruba people from the West African countries of Nigeria, Benin, and Togo.

Puerto Rico’s unique heritage can be seen across the island in its art and architecture.

Romance: St. Lucia

Lush natural beauty, soaring mountain landscapes highlighted by the UNESCO World Heritage Pitons, and multi-hued sunsets make St. Lucia a paradise for couples and an ideal Caribbean romance destination.

The scenery creates a dreamy backdrop for St. Lucia activities that bring lovers together: Picture detoxifying mud baths and relaxing hot-bath treatments at the volcanic Sulfur Springs in Soufrière and strolls through the Botanical Gardens’ flowery canopy. Couples can also opt for more adrenaline-inducing pursuits, from helicopter tours to zipline and horseback excursions.

There’s plenty of romance in accommodations too. The suites at hilltop luxury resorts Anse Chastanet and Ladera were built with fourth “open” walls that overlook the Pitons.

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Destination spa resort BodyHoliday reopened in October with programs that couples will appreciate, including (if they need some separate “me” time) a personalized Wellness Rehabilitation that incorporates relaxation techniques, fitness programming, holistic nutrition, and spa treatments. Beachfront sister property Rendezvous has also reopened with a focus on amenities and services designed to help couples to “reinvigorate” their relationships, including intimate, private beachfront dinners with chef-designed menus and “date nights” with champagne service and live entertainment. Couples planning destination weddings will find buy-out options here so they can create an on-property “bridal bubble.”

Family-friendly: Dominican Republic

Infinite stretches of coconut-palm-lined, white-sand beaches, and upscale resorts are de rigueur in the Dominican Republic’s Punta Cana district, the Caribbean’s all-inclusive resort kingdom and an easy win for families. Dozens of U.S. flights connect daily with the Punta Cana International Airport, and although the phrase “all-inclusive” can raise some travelers’ eyebrows, the combination of accommodations, cuisine, amenities, facilities, and activities makes this type of resort a hassle-free option, especially for family trips. You don't need to be stuck on campus the whole time though; resorts’ tour desks can arrange off-property excursions, such as coastal catamaran tours.

Properties range from family-themed to adults-only and include branded properties familiar to sun-and-fun-seeking U.S. travelers.

Nickelodeon Punta Cana is a haven for families with its seven flexible accommodation categories, including two- and three-bedroom “super villas” measuring 2,200 square feet. Kids (and their parents) can cool off at the Aqua Nick water park. Plaza Orange features live entertainment and family-friendly movie premieres, while kids can meet their favorite Nickelodeon characters throughout the day at Character Central.

The “ecochic” Club Med Michès is at the other end of the design spectrum. Located on pristine Playa Esmeralda, a barely touched coastal region surrounded by tropical forest, the property emphasizes sustainability across four distinct boutique “villages,” each offering customized environments, activities, and accommodations. It's a family-friendly option, thanks to kid-focused amenities, but it also caters to parents who may need the occasional break at one of its adults-only areas.

For grown-ups looking to ditch the kids entirely, the D.R. has plenty of adults-only properties, including TRS Cap Cana Hotel, where they’ll find the Zentropia Palladium Spa & Wellness Centre, an Ibizan-style beach club, and à la carte eateries serving Argentinian and Japanese fare. Or they can check into Breathless Punta Cana and burn off a few calories under tall palms with beachside fitness classes, or pump up the jam at the resort’s swim-up bar and multi-level Freestyle Pool, featuring live DJ music and curated cocktails.

Bonus: Belize for Adventure

While Belize is not an island, its prime coastal location on the Caribbean Sea makes it feel like one. What's more, the temperate weather, many direct flights from the U.S., and the fact that the country's official language is English, all make Belize a great—and often overlooked—warm-weather vacation option. The country is a wonderland of natural attractions, with extensive cave systems, lush jungles, and world-class dive sites. Combined with diverse cultures and historic treasures, Belize stands at the forefront of Caribbean adventure destinations.

Belize is a nexus for Maya, Caribbean, Garifuna, and even Mennonite cultures. English is the official language, although Belizean Creole is the most widely spoken.

The Maya civilization flourished in the region from 1500 B.C.E. through 1200 C.E., leaving behind archaeological sites now open to visitors. Several are located within Belize’s caves, which are accessible via guided tours that can range from easy walks to challenging excursions that require spelunkers to squeeze, crawl, climb, rappel, and swim through different sections.

Cave’s Branch Adventure and Jungle Lodge offers adventure-themed stays in the Belizean rain forest. Travelers can select their degree of exposure to nature, with “tree house” accommodations located 200 feet above the Caves Branch valley or jungle bungalows and cabanas located deep within the rain forest and equipped with separate air-conditioned and screened-in rooms, plus outdoor showers.

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