Escape To The Tropics: The Top Five Caribbean Islands To Visit This Winter

Long before Weezer was fantasizing about an "island in the sun" to post-punk teenagers in the early aughts, the Beach Boys were enticing yuppies with promises of a "tropical contact high" while Tom Cruise mixed drinks beachside in the cult 80s movie, Cocktail. Yet, the appeal of the tropics has even longer roots in popular culture than the recordings of Rivers Cuomo or Brian Wilson–there was a tourist presence in the islands as early as the 1880s. And with its turquoise waters, pink-sand beaches, and swaying palm trees, it's not difficult to see why, a century later, legions of snowbirds still make their annual descent to this tropical paradise every single year.

With over 7,000 islands in the Caribbean Sea, the choice of where to vacation during the winter months is no small task–though travelers can become unimaginative once the temperature drops below freezing. Though the Beach Boys famously sang about taking a would-be lover to Aruba or Jamaica, there are many more islands to visit in the Caribbean, some so unknown that they would surprise even the most well-seasoned traveler. Other islands, however, remain popular year after year—often for a good reason. As such, we've included a mixture of both in our selection below.

Taking into consideration privacy, revelry, and, of course, relaxation, we've rounded up the five best islands to visit right now–or, right when snow begins to fall in your (suddenly dismal) hometown. Read on for your ultimate guide for where to vacation in the Caribbean this upcoming winter.

New Providence, The Bahamas

With over 2,400 Cays and 700 islands in the Bahamas (of which only 30 are inhabited), the archipelago is a paradise for sailors, sun-worshippers, conservationists, and would-be pirates alike (at least pirates by the Jimmy Buffett definition of the term.) Though the Bahamas is named after its famously aquamarine coastline (the country's name is derived from the Spanish term Baja Mar, which means 'clear waters'), there's much more to this island nation than meets the eye—however visually appealing its tropical surfaces may at first appear.

The rich cultural heritage of the Bahamas is evident in the festivals and events held throughout the year, as well as in the cooking, dancing, and (yes) rum-distilling that can be found throughout Nassau and the outer islands to the present-day. We recommend visiting the Bahamas Museum to learn more about the island's history, signing up in a Tru Bahamian Food Tour to discover the ancestry embedded within local dishes, and participating in a People-To-People experience to dine in the home of a local family. 

A quick flight from Miami, the Bahamian islands are one of the most popular tourist destinations for travelers year after year—and this winter, it's imperative that visitors continue that tradition. In the aftermath of the Category 5 Hurricane Dorian that struck the northern Bahamas this fall, the news was flooded with images of the destruction. Hurricane Dorian peaked over the Abaco Islands on September 1st, and was the worst natural disaster in the country's history, as well as the worst tropical cyclone to hit the Bahamas on record,

But many of the popular tourist destinations, including the island of New Providence (home to Nassau and Paradise Island), were unaffected. And today, all the outer islands are receiving visitors except for the Abaco Islands, which will take longer to recover. The fastest way to aid that recovery—not just for the islands of Abaco but throughout the entire island chain itself? Book a flight. Visit this winter. Your tourist dollar counts now more than ever—and thanks to hotel and flight incentives—they now go further than ever, as well. And, best of all, you'll be showing a place that you love some love in return.

Dominica, Windward Islands

Dominica isn't just one of the most breathtakingly beautiful islands in the Caribbean, it's one of the most breathtakingly beautiful nations in the entire world. And, on the rare chance that you're aware it exists, you're probably mispronouncing its name. For starters, it's 'DOM-ih-NEE-kə,' not to be confused with the Dominican Republic, which is only 1,000 kilometers northeast from Dominica but feels infinitely further away still. 

Located in the Eastern Caribbean Sea, Dominica is known as the "Nature Island" of the Caribbean, and it is decidedly wilder and less tamed than many of its neighbors in the Windward Island chain (including, of course, our next selection below.) With its boiling lakes, champagne reefs, volcanic valleys, and tropical rainforests, Dominica is absolute heaven for the outdoors-lover, or the nature-enthusiast, or even the wellness-warrior. The herbs growing in Morne Trois Pitons National Park are rumored to cure just about anything, and the year-round sperm whale population frolicking in the water just off the coast of Roseau is a guaranteed dose of perspective on a sunny afternoon.

Dominica has thus far remained lesser-known to would-be tourists than the neighboring French isles of Martinique and Guadeloupe (so-called by locals on-island because, unlike Dominica, which achieved its independence in 1978, both islands remain under French rule.) But the times, they are-a-changing: Dominica covered the April 2019 issue of Travel & Leisure and is receiving increased international attention with the October unveiling of the Cabrits Resort & Spa Kempinski, a luxury property set amongst Cabrits National Park with a spectacular view overlooking Douglas Bay. 

Yet, even before this gorgeous addition to the hotel landscape, Dominica boasted several charming, sophisticated, and utterly bliss-inducing properties from coast-to-coast—notably the tranquil, coastal oasis of Pagua Bay House in Marigot, and the elegant seaside charms of Fort Young Hotel, in the nation's capital of Roseau. It is unclear how much longer such destinations will remain under-the-radar—and so, in short, the time to visit is now.

Barbados, Windward Islands

Though there's never a bad year to visit Barbados, this upcoming winter holds pride of distinction as the island's national homecoming. We Gatherin' Barbados 2020 is a celebration intended for all: "Bajans by birth, Bajans by descent, Bajans by choice… and those who love Barbados." And, honestly, in this day and age, who doesn't?

Though Barbados is celebrated for many reasons–its rich tradition of rum, legendary fish fry, distinct Bajan dialect and cultural heritage (a blend of West African and British)–the island's status as the homeland of Robyn' Rihanna' Fenty awards it a unique pride of place in the global imagination. Good news for all would-be visitors: The gorgeous island that produced the equally-gorgeous Rihanna does not disappoint. The tropical ambiance is picture-perfect (as is to be expected), and the island's attitude is distinctly warm and welcoming, albeit with some added flair.

Those looking for an example need look no further than the famed Oistins Fish Fry, held every Friday night, where septuagenarians dance to the music of the old and the new. Imagine Sam Cooke classics mixed with Drake's new album. (Which, as it happens, was inspired by Caribbean-dancehall–we have Rihanna to thank for that as well.) It's easy to imagine Rihanna sauntering around the scene with a wine glass in hand, liquor laws (or any laws, really) be damned. Thankfully, for non-divas among us, drinking outside on a Friday night at Oistins is not only permitted, but expected.

But there's more to Barbados than fried fish, live music, and a good time. Visitors should spend an afternoon at the Barbados Museum, parts of which were first built in 1817, to gain a greater understanding of the nation's history. Lesser-known as a Caribbean surf capital, Barbados also boasts some of the best breaks east of Fiji. And an evening with the expert mixologists at the Colony Club provides the perfect crash-course in the island's rich tradition of rum-making. Bajans like to claim that, even if they never invented rum, they certainly perfected it–though that is hotly contested by our next selection, located 100 kilometers to the west in the Windward Islands.

Grenada, Windward Islands

Tucked away to the east of Barbados in the Windward Islands, Grenada is one of the Caribbean's best-kept secrets. With its lush tropical forests and pristine coastline, the 'Spice Island' of Grenada shares the wondrous natural beauty of its neighbor to the north, Dominica. Plus, the country's name is similarly subject to mispronunciation. Leave your high school Spanish behind when arriving in Grenada: It's 'Gree-nay-da,' not 'Gra-nah-da,' the latter of which rightfully rhymes with the Spanish Armada, the home-country to the island's European counterpart (in name alone, of course). 

But while the Nature Island is famed for its volcano-trekking and rainforest hiking, we recommend more liquid-based pursuits while visiting the Spice Island: Rum-tasting and sailing, namely. The island's protected coves make it a favorite amongst sailors, and there is no better activity on a sunny afternoon than sailing upon a Caribbean Schooner, rum punch in hand, with Captain Danny. But be warned: He makes them quite deadly. This, of course, is in keeping with the rum legacy on the island: Check out the outrageously high alcohol proof of the locally-grown and insanely popular varieties on sale at the River Antoine Estate for evidence.

Unlike Barbados to the west, whose exposed position outside the Caribbean island chain results in the island's legendary swells, Grenada offers a safe, enclosed harbor for fishermen, sailors, and vacationers alike. While some Caribbean nations can be chilly in January and February, Grenada coasts along at a balmy temperature in the low to mid-eighties. Plus, the scenery and ambiance are as beautiful as any you'll find on even the most celebrated of luxury islands in the Caribbean.

The French influence on Grenada's culture is reminiscent of St. Barth's, while its breathtaking pastel coastline is echoed in nearby Mustique, only 101 kilometers away. What Grenada doesn't share is these other islands' snobbery, however. Book a villa at the boutique Mount Cinnamon Resort, overlooking Grand Anse Beach, to get a taste of luxury and island-relaxation all at once–a real rarity these days.

For the high-flying traveler who seeks luxury at all costs, look into booking Calivigny Private Island–also known as the site of Justin Bieber's 21st birthday party, though the property's sophisticated history belies any unbecoming association with America's favorite young tattoo-enthusiast. The main house was designed by Richard Frinier and Oscar de la Renta (who knew a thing or two about tropical luxury, having developed the Puntacana Resort & Club in Punta Cana, Dominican Republic), while the modern portion was overseen by the British designer, Christopher Guy. With marble floors, private Jacuzzis, and contemporary art, what more could a young (or young-at-heart) Master of the Universe possibly need?

South Caicos, Turks and Caicos Islands

For our next choice, we're leaving the blessedly laid back island of Grenada for the equally low-key tropical getaway that is South Caicos. Though part of the famously glitzy Turks and Caicos Islands, South Caicos is underrated amongst the sunbathing, tourist crowds who make the rest of the Caribbean islands slightly more crowded around the holidays. In South Caicos, you're more likely to spot a wild donkey sauntering poolside at sunset than a selfie-taking teenager (and amen for that.) And the time to visit is now–before the rest of the world catches on, of course.

Sailrock Resort was the first luxury offering to open on this sleepy island, and the property's understated elegance, mixed with outrageously romantic vistas available at every turn, fully capitalized on the picturesque color palette of Turks and Caicos. The limestone beaches are dotted with touches of pink, the turquoise sea so crystal-clear that, in shallower waters, it nearly looks lime green. With its wildness and seclusion, South Caicos distills the most beautiful elements of Providenciales into its own utterly intoxicating tropical blend.

Most guests don't transfer to a second inter-island flight when they arrive at the airport in Providenciales, the most populated(and popular) island in the archipelago. Even regular visitors (and celebrities) are unaware of the blissful serenity awaiting one brief seaplane ride away. Taylor Swift, she of Lover fame, spent the past 4th of July in Turks and Caicos with her British boyfriend (he, too, now of Lover fame.). That she decided to forgo her annual party in the equally glitzy (though decidedly colder) seaside town of Watch Hill says enough about the destination's appeal. Yet, if she'd forgone Providenciales for the secluded environs of South Caicos, it's less likely that paparazzi would have caught her frolicking on the beach with said beau.

But, travelers shouldn't be dissuaded by the island's reputation as a hyper-obvious setting for romance. Why wait for a lover when you can book a villa with platonic life partners? What better way to capitalize on the coastal beauty, expert cocktails, and relaxing spa treatments than with a group of friends? There's never a wrong time for a trip to South Caicos–for a vacation where you thoroughly treat yourself—but there's also no time like the present.