The Caribbean’s sunny skies, turquoise waters, and magnificent natural landscapes are among the many reasons the region is a perennial favorite with travelers. Add in engaging culture, unique cuisine, and extensive air connections to U.S. gateways and it’s clear that destinations like Anguilla and Puerto Rico will continue to top wish lists. The islands are alluring for families seeking a memorable trip, couples in search of the ultimate romantic getaway, and adventurous solo travelers. These are some of the best Caribbean islands to visit based on an array of interests.
In this article
The Caribbean islands we most recommend planning a trip to include:
- Best for Beaches: Anguilla
- Top Luxury Pick: Nevis
- Aquatic Adventure: British Virgin Islands
- Cultural Hot Spot: Puerto Rico
- Romantic Retreat: St. Lucia
- Family Friendly: Dominican Republic
“With 33 beaches, several islands and cays, and more than 100 restaurants, Anguilla packs a lot into its 35 square miles,” Sarah Greaves-Gabbadon said when Afar picked the island for its 2022 Where to Go list.
Courtesy of Anguilla Tourist Board
Anguilla: Best for Beaches
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. And added bonus? They’re uniformly uncrowded. Visitors can take a powerboat trip from Road Bay in the Sandy Ground district to Sandy Island, a sliver of white-sand beach eight minutes from the shore. The exclusive private island is ideal for an afternoon of easy relaxation sampling spiced shrimp kebabs or lobster salad 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. A standout is the Aurora Anguilla Resort & Golf Club, a beachside luxury resort located on the grounds of the highly regarded former CuisinArt property. It delivers three suite categories, a collection of villas offering generous outdoor spaces, and a private jet fleet dedicated for guests’ exclusive use. Other options include 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.
The Four Seasons Resort Nevis offers a variety of excursions, including a catamaran trip and a tour tracing Alexander Hamilton’s life here as a child in the mid-1700s.
Courtesy of Four Seasons Resort Nevis
Nevis: For Luxury
Encompassing a scant 36 square miles, Nevis offers travelers a fast-disappearing Caribbean experience with no tall buildings, crowds, or chain restaurants. Its easygoing charm belies an outstanding collection of luxury resorts and high-end dining venues.
A singularly green island even by Caribbean standards, Nevis’s 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.
The 350-acre beachfront Four Seasons Resort Nevis, the island’s largest property, reopened in 2021 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.
Built on the site of a 300-year-old sugar plantation, Montpelier Plantation & Beach embraces a laid-back vibe 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: think sous vide calamari salad, crispy pumpkin ravioli, and deconstructed coconut Key lime pie. Boutique luxury resort Golden Rock meanwhile—which has only 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 cuisine at the 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.
The Moorings boasts a modern fleet of more than 400 active yachts across the globe, including in the British Virgin Islands.
Courtesy of the Moorings
British Virgin Islands: Aquatic Adventures
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 that includes a captain, chef, and first mate.
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.
Sampling Puerto Rican street food is a must in the coastal Piñones region.
Courtesy of Discover Puerto Rico
Puerto Rico: Food & Culture
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 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 (mashed plantains with pork rinds), bacalaitos (codfish fritters), and pasteles (pork-filled tamales) 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 settlement by Yoruba people from the West African countries of Nigeria, Benin, and Togo.
St. Lucia’s striking scenery offers a dreamy backdrop for a couple’s retreat.
Photo by Shutterstock
St. Lucia: For Romantic Getaways
Verdant natural beauty, soaring mountain landscapes highlighted by the UNESCO World Heritage Pitons (volcanic plugs), and multi-hued sunsets make St. Lucia an ideal Caribbean romance destination.
The scenery creates a dreamy backdrop for activities for couples: 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. Destination spa resort BodyHoliday offers programs that couples will appreciate, with a focus on relaxation techniques, fitness programming, holistic nutrition, and spa treatments.
The Dominican Republic is full of family-friendly hotels with suitable activities.
Photo by EMS-DOP/Shutterstock
Dominican Republic: Family-Friendly
Seemingly 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 if you’re traveling with kids. You don’t need to remain on campus the whole time; resorts’ tour desks can arrange off-property excursions, such as coastal catamaran tours.
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 “eco-chic” Club Med Michès Playa Esmeralda 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.
This article was originally published in November 2021 and was updated in November 2024 with new information.
