antigua caribbean winter vacation getaway
A placid beach on the isle of Antigua. (Photo: Luis Santos/Shutterstock)

What Are the Best Winter Retreats in the Caribbean?

I want some sun, sand, and drinks with umbrellas in them this winter. What are the most overrated and underrated Caribbean destinations?

antigua caribbean winter vacation getaway
Greg Melville

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Overrated destinations don’t exist—only unimaginative travelers. You can turn any trip, even to the lamest of foreign tourist traps, into a cultural adventure with a little planning and research. So, instead of focusing on a specific “overrated” country or town, I’ll point out a couple of popular, well-known resorts—which we’ll call “overrated”—that you can probably erase from your must-visit list. (Hint, you’ll notice that I can’t stand massive, self-contained, all-inclusive resorts filled with Americans who never venture off-property.) I’ll also recommend some quiet spots—for our purposes: “underrated”—that might be off your radar.

Coconut Beach Club, Antigua
Excellence, Punta Cana, Dominican Republic
Jungle Bay, Dominica
The Royal, Cancun, Mexico

Underrated Caribbean Retreats: Coconut Beach Club, Antigua

coconut beach club antigua caribbean travel winter getaways
Coconut Beach Club will get rid of your winter blues. (Luis Santos/Shutterstock)

I’m a huge fan of the safe, placid island of Antigua and its uncrowded beaches. The people—from the sailing partiers of Falmouth Harbor in the south to the shopkeepers of St. Johns on the north end—are warm and welcoming, as long as you remember to drive on the left side of the road. The Coconut Beach Club offers 59 wooden, open Caribbean-style cottages perched above the ocean, where you can watch the waves fall onto the long, white beach from the hammock or Adirondack chairs on your balcony. Rates start at $375 a night.

Overrated Caribbean Retreats: Excellence, Punta Cana, Dominican Republic

excellence dominican republic travel winter getaways
Excellence has it all, but can be covered in Americans. (Ted Murphy/Flickr)

To say that Punta Cana, on the eastern side of the island, gets a little overrun with American tourists is like saying that Wisconsinites sort of have a thing for cheese. It’s with good reason, though. Punta Cana’s sugary beaches, warm, shallow waters, and tropical climate are ideals of a Caribbean vacation. But if you’re going to the deservedly world-renowned, adults-only Excellence, you’re probably not planning to ever leave the property, which occupies a mile-long stretch of beach all to itself. Boasting nearly 450 rooms, nine restaurants, and a 4,500-square-foot fitness center, it practically dares you to find a reason to venture off its secluded confines. Rates start at $462 a night.

Underrated Caribbean Retreats: Jungle Bay Resort, Dominica

dominica caribbean travel winter getaways ecotourism
Dominica is covered in beautiful ecotourism locales. (Sorin Colac/Shutterstock)

Sleepy, barely-discovered Dominica is kind of like Costa Rica, just on its own island—verdant, hilly, and filled with tropical beauty. Domica attracts an outdoorsy set who prefer zip-lining and hiking through volcano-carved jungles over sunbathing. And the finest of the island’s small selection of eco-resorts is Jungle Bay. Its hardwood-framed cottages, etched into the steep hillside on stilts—some that require a 200-step climb from the main path—overlook the water and offer seclusion within the jungle. Rates start at $283 a night.

Overrated Caribbean Retreats: The Royal, Cancun

cancun travel winter getaways mexico caribbean
Cancun is the last place you should go if you're looking to relax. (Mike Liu/Shutterstock)

Cancun. Need I say more? The beach bars are like Venus flytraps filled with Jell-O shots, or something, but you really can have some non-Spring Break fun here if you try. There are the archeological sites at Chichen Itza and Tulum, the magnificent island of Isla Mujeres, and, of course, the beach at Cancun itself. One of the more highly-regarded resorts is the Royal—if you’re into sprawling, soul-sucking concrete palaces with 288 satellite-TV-equipped rooms, eight restaurants (with cuisine covering four continents), 14 bars, a jewelry store, and unisex beauty salon. Ugh. But hey, if that’s your thing, by all means. Rates start at $647 a night.