For beach-loving families, the Caribbean islands can be the ultimate in vacation bliss. But with almost 30 different countries — and a whopping 7,000 islands between them — how do you winnow it down to the one that’s right for you? The answer depends on a host of factors, including your travel style, kids’ ages and more. Take the tips below into consideration as you choose which part of this spectacular region to visit next.
With very young kids, Jamaica gets our top vote, thanks to the island-wide practice of providing expert nannies in many resorts and villas. Consider Grand Cayman for the great selection of beachfront condos in different price ranges as well as the clear, gentle water. Similarly, on Turks and Caicos, the calm seas are fronted by wide and pristine beaches with flour-soft sand that’s easy on tiny toes.
The key word for teens? Variety. This age group is notorious for getting bored, so choose an island with a diverse range of things to see and do. St. Lucia is a paradise for outdoor pursuits like ziplining, rainforest hikes and deep-sea fishing; kids old enough to try scuba diving will love the British Virgin Islands (BVIs), Curacao and Bonaire. If you have die-hard shoppers, hit Aruba, St. Martin/St. Maarten, St. Thomas or Grand Cayman. And you can’t go wrong with a splashy resort that provides plenty of age-appropriate programming, such as Atlantis in the Bahamas or one of the three Beaches locations in Jamaica and Turks and Caicos.
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There was a time when you’d never go to the Caribbean for the food, but that’s changing, thanks to a boom in restaurants and newfound pride in native cuisine. Many of the isles still import the bulk of their ingredients, so if eating local matters to you, consider an island with a rich food tradition like Puerto Rico or Jamaica. If you just want a fabulous meal no matter where it was sourced, good bets include Anguilla, St. Barths (the prime island for upscale French food), Martinique or St. Martin/St. Maarten.
Bigger is better here — smaller islands tend not to offer the wealth of adventures found on larger ones. Head to the Dominican Republic, Puerto Rico, St. Lucia or Jamaica for thrills like windsurfing, canyoning, off-roading, kiteboarding and challenging hikes. Dominica, known as the “nature island,” feels rugged and wild; what it lacks in beaches it makes up for in spectacular peaks, showy flora and waterfalls. Also, while it’s not an island, Mexico’s Riviera Maya is on the Caribbean coast and offers adventure parks, ziplines, rappelling, cenotes (submerged sinkholes) for snorkeling and more.
Craving time off the grid? The Caribbean has no shortage of luxe hotels and resorts geared toward leisure and lolling. Many of our favorites are scattered along Grace Bay, Turks and Caicos’ most gorgeous beach. We’ve also loved relaxing at secluded properties in the Dominican Republic and Jamaica, which feel a world away from the bustle of both islands. To get even farther off the grid, opt for Anguilla, the Bahamas’ Eleuthera or Abaco Islands, Peter Island in the BVIs, St. John (much of which is protected parkland) or the sleepy Grenadines.
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Although the Caribbean doesn’t get a lot of credit as a cultural destination, the region has a layered and fascinating history that’s still evident throughout the islands. The most famous example is the Tulum ruins on the Riviera Maya, but don’t overlook the colonial-era sites in Puerto Rico and Antigua, or the long tradition of British influence in Barbados. And Cuba’s tumultuous past still colors every aspect of daily life and travel on this unique island.
There’s a bit of a tradeoff involved in choosing an island that’s easy to reach by plane — you typically lose the sense of escape that comes with vacationing somewhere small and remote. That said, not having to endure a long transfer or puddle-jumper ride, after a connecting flight to a major hub like Montego Bay, is well worth it for many parents, especially with younger kids. For direct and nonstop flights from the U.S., look into Puerto Rico, Barbados, the Bahamas, Jamaica, Grand Cayman and Aruba.
With the exception of a few smaller and more rustic islands like Dominica, it’s not hard to find luxury throughout the Caribbean — top-end resorts pepper the region. Still, St. Barths has long been the go-to island for luxe seekers due to its tony vibe and air of glamour. Anguilla, though slightly more laid back, is fast catching up. For the ultimate in pampering, book a stay on a private island like Necker Island in the BVIs or Parrot Cay in Turks and Caicos — the sense of indulgence and escapism is unforgettable.
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