Each Caribbean island has its own draw, like Anguilla’s long white beaches.
Photo by pics721/Shutterstock
This article was originally published in November 2021 and was updated June 6, 2026, with new information. Laura Begley Bloom contributed to the reporting.
The Caribbean is home to thousands of islands. Some are all about long beach days and laid-back luxury. Others are known for sailing, food, culture, family-friendly resorts, or year-round sunshine. To help narrow down the options, we’ve picked the best spots for a range of travel styles and interests.
A trip to the Bahamas could include a day at a festival like Junkanoo and another at a turquoise beach like Cabbage Beach.
Photo by jo Crebbin/Shutterstock (L); photo by Sandra Foyt/Shutterstock (R)
The Bahamas: for arts and culture
Most travelers visit the Bahamas for its beaches, but the archipelago’s arts and culture scene is also getting serious attention. Proof positive: In 2026 the country was invited to take part in the Venice Biennale with a pavilion featuring Bahamian artists John Beadle and Lavar Munroe. Visitors can check out the country’s creative spirit at the National Art Gallery of the Bahamas, which showcases both contemporary and historic works. Another must-see is Hillside House, where sculptor Antonius Roberts transformed a Nassau home from 1840 into a gallery, studio and gathering place for artists.
Beyond Nassau, visitors can sign up for the country’s people-to-people program, a deep dive cultural experience that matches visitors with local residents from various islands who volunteer to spend the day sharing their real Bahamian life. The program has been going on for more than 50 years, and activities might include going to a fish fry, family gatherings, seeing their homes, going to church, or just hanging out and getting to know each other.
Another way to dip into Bahamian culture is through its year-round festivals, including the costumed dance performances of Junkanoo in the winter and the Goombay summer festivals.
Anguilla has 33 beaches, several islands and cays, and more than 100 restaurants.
Courtesy of Anguilla Tourist Board
Anguilla: for beautiful beaches
Anguilla is small but mighty, with one of the highest concentrations of great beaches in the Caribbean—33, to be exact. Across the island, the sand is soft and white, the water is clear, and the beaches are rarely crowded. Each has its own personality. Meads Bay is lined with some of Anguilla’s top restaurants (don’t miss Blanchards, with both fine dining and tables on the sand). Rendezvous Bay is known for calm swimming conditions. Shoal Bay is popular for snorkeling. The crescent-shaped Maundays Bay is home to the Santorini-inspired Cap Juluca, a Belmond Hotel.
Beach bars are practically a way of life here. On Sandy Ground, you’ll find Elvis’ Beach Bar, which is built from an old sailboat and hosts legendary full moon parties. Sunshine Shack on Rendezvous Bay is famous for its ribs and live music. To get away from it all, hop on a boat from Sandy Ground to Sandy Island, a tiny offshore cay where you can order spiced shrimp kebabs and rum punches.
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 quiet luxury
When people think of Caribbean luxury, they often picture St. Bart’s. Nevis offers a different kind of quiet luxury, where historic plantations take the place of beach clubs and bottle service. The 350-acre Four Seasons Resort Nevis is the island’s largest property. Guests can tee off beside a centuries-old windmill on the Robert Trent Jones II golf course and swim in three infinity-edge pools. Just next door, the new Palm Garden Nevis is a six-acre private estate powered entirely by solar energy. There are two villas for rent and one of the world’s largest private collections of palm trees.
Travelers looking for something even more low-key can check into Montpelier Plantation & Beach, built on the site of a 300-year-old sugar plantation and known for its private beach lined with hammocks and cabanas. The resort’s Mill Privee restaurant serves imaginative takes on Caribbean cuisine, including crispy pumpkin ravioli and deconstructed coconut Key lime pie.
Related: The 31 Best Luxury Resorts and Hotels in the Caribbean You Should Book Right Now
Massive granite boulders create pools at the Baths in Virgin Gorda.
Courtesy of British Virgin Islands
British Virgin Islands: for aquatic adventures
More than 60 islands and cays make up the British Virgin Islands, often called the Sailing Capital of the World. Travelers who want to embrace the sailing lifestyle can charter a yacht with Dream Yacht Worldwide or stay at the Bitter End Yacht Club, a longtime favorite with sailors. Days in the BVI are spent hopping between islands and dropping anchor in hidden coves. No visit is complete without a stop at the Baths on Virgin Gorda, where massive granite boulders form sheltered beachfront pools and crevices for exploring. Besides sailing, there are plenty of other ways to get out on the water, including paddleboarding, kayaking, kitesurfing, surfing, and deep-sea fishing. Divers can explore one of the Caribbean’s most famous underwater sites, the RMS Rhone (which sank in 1867), or venture to Wreck Alley (a collection of historic shipwrecks).
Sampling Puerto Rican street food is a must in the coastal Piñones region.
Courtesy of Discover Puerto Rico
Puerto Rico: for food and culture
Puerto Rico is home to an exciting food scene that blends Spanish, Indigenous Taíno, African, and American influences. One of the best ways to sample Puerto Rican cuisine is on a food tour with Spoon, which takes travelers to family-owned restaurants and markets in San Juan. Classic dishes not to miss include mofongo (mashed plantains with pork rinds), bacalaitos (codfish fritters), and pasteles (pork-filled tamales). Another must is the Pork Highway, where roadside stands serve up slow-roasted pork. And then there are next-gen restaurants putting a fresh spin on island traditions. Following a $70 million transformation, Wyndham Grand Rio Mar recently unveiled several new culinary concepts, including Amaya (a Spanish-inspired restaurant led by chef Daniel Lugo, a protégé of José Andrés), Roots Coastal Kitchen (with farm-to-table Caribbean comfort food), and the Vault (a speakeasy cabaret hidden behind a former bank vault door). In Rincón, the sustainable Chef’s Garden combines modern techniques (fermentation, foam) with ancestral ingredients.
Related: For Some of the Best Food in Puerto Rico, Head to the “Pork Highway”
St. Lucia’s striking scenery offers a dreamy backdrop for a couple’s retreat.
Photo by Shutterstock
St. Lucia: for romantic getaways
St. Lucia is one of the Caribbean’s most romantic destinations, thanks in large part to its dramatic scenery. The twin Pitons create a spectacular backdrop for everything from adventurous outings to romantic resorts. Spend the day soaking in the mud baths and hot springs at Sulphur Springs (the world’s only drive-in volcano) or strolling through the Botanical Gardens. Adventurous couples can opt for an ATV excursion with Eastern Exotic Tours (which passes through banana farms and local communities) or Wild Wheels (which explores secluded beaches and rainforest landscapes).
When it comes to romantic accommodations, St. Lucia delivers. The suites at hilltop luxury resorts Anse Chastanet and Ladera were built with fourth “open” walls that overlook the Pitons. Windjammer Landing has candlelit dinners on the sand, sunset cruises, and villas with plunge pools. For couples seeking even more privacy, Windjammer recently opened La Belle Hélène, a 10-suite villa estate on the other side of the island with jaw-dropping views of the Pitons.
Related: It’s Not Worth Visiting the Caribbean if You Never Leave the Resort. Here’s How to Travel Deeper
The Dominican Republic is full of family-friendly hotels and activities, like whale watching.
Photo by EMS-DOP/Shutterstock
Dominican Republic: for family-friendly vacations
With seemingly infinite stretches of white-sand beaches, plenty of flight connections, and a wide range of all-inclusive resorts, the Dominican Republic is an easy win for families. In Punta Cana, the country’s tourism hub, Nickelodeon Punta Cana is a haven for families. You’ll find character meet-and-greets, live entertainment, the Aqua Nick water park (where you can get slimed), and plenty of options for picky eaters.
Travelers looking for a quieter alternative should consider Miches, an emerging destination about 90 minutes north of Punta Cana that’s home to more than 30 miles of beaches. Set on secluded Playa Esmeralda, the new Zemi Miches Punta Cana All-Inclusive Resort, Curio Collection by Hilton encourages families to connect with Dominican culture through artisan workshops, chocolate-making classes, music, dance, and more. Families can also venture beyond the resort for horseback riding, snorkeling, waterfall excursions, and seasonal whale watching.
In Aruba, the weather is perfect for all kinds of outdoor enjoyment.
Photos by Michelle Heimerman
Aruba: for great weather for any activity
For travelers chasing sunshine, Aruba is hard to beat. There’s nearly perfect beach weather year-round, with more sunny days than any other Caribbean island. Rainfall is rare. And thanks to its location in the southern Caribbean outside the hurricane belt, Aruba is an appealing choice in summer and early fall when other islands are keeping a nervous eye on the forecast.
Besides keeping the temperatures comfortable, the island’s steady breezes make it ideal for outdoor activities such as windsurfing, kitesurfing, and sailing. Those seeking more adventure can try horseback riding or hiking in Arikok National Park or diving to the Antilla Shipwreck.
Nature lovers can also visit the Butterfly Farm, where hundreds of colorful butterflies flutter through a tropical garden setting. The newest place to stay is the Westerly, an oceanfront hotel-within-a-hotel that opened at the Hilton Aruba Caribbean Resort & Casino. The property brings a boutique-style experience to Aruba’s first luxury resort, complete with an adults-only rooftop retreat, Terrace on 10, known for its panoramic island views.
Related: The Adventure Lover’s Guide to Aruba
