6 Caribbean vacations that check every travel style

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Whether you plan around beaches, nightlife or food, experts have a Caribbean trip for you

With its sun, sea and slower pace, the Caribbean beckons travelers looking for an escape from daily life. It’s easier to forget about your job, your commute or your next parent-teacher conference when you’re lazing on a tropical beach.

“That paradise vibe is very attractive right now as everyone is burned out and grieving from everything the pandemic has brought us,” says Terika L. Haynes, owner of Dynamite Travel.

But the region is not a monolith. Stretching from the Gulf of Mexico to South America, every pocket of the Caribbean offers something unique to visitors. To find the right version of paradise for you, we spoke with Caribbean travel experts to share their recommendations. Here are six ideas, whether you’re most into diving, unwinding, dancing or dining.

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For the ultimate beach trip: Antigua

If a post-card-worthy beach is what you’re after, Haynes suggests Antigua (pronounced an-TEE-guh). With Antigua advertising 365 beaches, “you could go to a different beach every day of the year,” Haynes says.

A small island that is easy to explore, Antigua has soft sand and clear, blue water. You may want to post up at a resort and enjoy what’s on your doorstep, but “with so many beaches to explore you may want a [rental] car to beach-hop,” Haynes says.

Laura Sangster, the founder of Caribbean Journey who has been to the region more than 150 times, says Guana Island in the British Virgin Islands is the best beach option. “If you want pure white sand, crystal-clear water and to share the beach with only a handful of other guests, you have to go,” Sangster says. An 850-acre private island with seven beaches, Guana also has lush tropical forest and mountains that are great for hiking. All of that comes at a price: An all-inclusive Sea View cottage at the Guana Island hotel is listed at $890 a night.

For eating and drinking: Anguilla

Joshua E. Bush, chief executive of the travel agency Avenue Two Travel, calls Anguilla “a culinary paradise within paradise.”

Haynes feels the same. With influence from Indigenous Caribbean, African, French, Spanish and English cuisines, “Anguilla is known as the culinary capital of the Caribbean,” she says. “You can experience great dining and still enjoy really pretty beaches.”

Haynes says travelers love Anguilla’s culinary variety, from its farm-to-table dining scene and roadside barbecue stands to its fine-dining restaurants run by Michelin-awarded chefs. Don’t miss delicacies such as grilled spiny lobsters, barbecue ribs with fried johnny cakes or pigeon peas with rice, Anguilla’s national dish.

Sangster picks Saint Barthélemy, or St. Barths, for food. Shayna Mizrahi, founder and CEO of Vive Voyage, agrees. “The quality of food and culinary options on St. Barths is unparalleled in the Caribbean,” she says, vouching for the island’s range of casual to high-end restaurants. As an overseas collectivity of France, St. Barths is known for its French cuisine as well as West Indian and Creole. The move here is ordering fresh seafood; one of Mizrahi’s memorable meals was a whole sea bass barbecued over an open fire at Gyp Sea beach club.

Amina Dearmon, founder and owner of Perspectives Travel, votes for Puerto Rico, birthplace of the piña colada. “The food scene in San Juan is influenced by all of the cultures that have inhabited the city over its 500-year history,” she says. “Take a food tour so that you can get a mix of history and taste tests, and then go back to your favorite restaurants for full meals.”

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For budget flights: The Bahamas

While technically in the North Atlantic Ocean vs. the Caribbean Sea, the Bahamas works as an island destination for travelers worried about overspending.

Mizrahi points to the extensive list of hotels, resorts and all-inclusive properties available at a range of price points. Plus, “flights to the Bahamas are usually the least expensive as well,” she says.

Dearmon also vouches for the Bahamas. “Travelers will appreciate that some of the most sought-after Bahamian cuisine like conch fritters, grouper, and peas and rice are well-priced and plentiful,” she says.

Hayne’s budget option is Mexico’s Riviera Maya. The region stretches south of Cancún to Tulum, and it “works really well for groups and families who need good value for their money,” Haynes says. Additionally, getting to Mexico tends to be a shorter and cheaper ordeal than flying to other parts of the Caribbean.

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For nightlife with stamina: Barbados

For locals in Barbados, “everyone seems like they want to have a good time,” Haynes says. For evidence, she points to the fish fry, a big street party with food, drinks and dancing that takes place every Friday in the town of Oistins. She also likes that there is a diverse spread of nightlife options, from clubs bumping house music to more intimate jazz spots. If you time your trip right, you can visit for Barbados’s version of Carnival, called Crop Over. “It’s 24/7 parties,” Haynes says.

Dearmon recommends St. Barths, where “beach club reservations are almost as important as hotel reservations,” she says. Even though the party scene starts early in the day, the music plays late into the night.

“When the sun goes down, the DJs come out to play a set while you enjoy dinner at island offshoots of some of the most renowned French restaurants in the world,” she says. “After dinner, enjoy live music, nightclub vibes, or head back to a beach club for a nightcap before doing it all again the next day.”

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For a friends trip: Dominican Republic

Joan Roca, the CEO and founder of the members-only travel-planning company Essentialist, says the Dominican Republic makes for a great location for a trip with friends thanks to its range of accommodations (villas, resorts, hotels) and healthy mix of beach, nature, restaurants, and nightlife options.

Haynes plans a lot of travel to the Dominican Republic for families and destination weddings. “It has a great inventory of really nice resorts that are good for groups,” she says. That inventory is growing; Haynes notes the country had an influx of properties open in the last year.

If your group will be coming in from different cities, Sangster says, it’s important to pick a more popular part of the Caribbean that has a lot of flight options. Some examples are Jamaica, the Dominican Republic and Riviera Maya. Those options also tend to be good for price-sensitive travelers. “Most of the larger islands can be done on a budget,” she says.

For hiking and diving: Saba

For “nature lovers who want to get away,” Haynes recommends the five-square-mile island of Saba. A 12-minute flight or 90-minute ferry from Sint Maarten, Saba is best known for its charm and excellent hiking. The island is the top of a volcano that last erupted in 1640.

There’s a catch: Saba doesn’t have sandy beaches like most of the Caribbean. Instead, visitors can enjoy swimming and world-class diving in the surrounding Saba Marine Park. Because the island restricts fishing and anchoring, there is a healthy population of more than 150 species of fish around the underwater lava flows and hot springs.

Both Sangster and Dearmon choose Dominica for their off-the-beaten-path destination, citing the island’s eco-adventures, great hotels and culture.

“The lush greenery of the island will be the first thing that strikes you,” Dearmon says. “The rainforests, mountains, and waterfalls, are the natural wonders that make Dominica a destination for hiking, diving, and wellness vacations.” She recommends visitors take trips to the Portsmouth Saturday Market and Kalinago Territory, a 3,700-acre region of the island where descendants of Dominica’s original people still live.

More travel tips

Vacation planning: Start with a strategy to maximize days off by taking PTO around holidays. Experts recommend taking multiple short trips for peak happiness. Want to take an ambitious trip? Here are 12 destinations to try this year — without crowds.

Cheap flights: Follow our best advice for scoring low airfare, including setting flight price alerts and subscribing to deal newsletters. If you’re set on an expensive getaway, here’s a plan to save up without straining your credit limit.

Airport chaos: We’ve got advice for every scenario, from canceled flights to lost luggage. Stuck at the rental car counter? These tips can speed up the process. And following these 52 rules of flying should make the experience better for everyone.

Expert advice: Our By The Way Concierge solves readers’ dilemmas, including whether it’s okay to ditch a partner at security, or what happens if you get caught flying with weed. Submit your question here. Or you could look to the gurus: Lonely Planet and Rick Steves.

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