An Insider’s Guide To The Best Caribbean Islands To Visit In January

by Julia on November 25, 2019

The Caribbean, with its stunning array of paradisiacal islands and crystal-clear waters, has long been a popular destination, especially in January with snowbirds looking to enjoy some winter sunshine. And with each island offering a totally different experience, there really is something for everyone in this exotic wonderland. For those struggling to decide where to go, here are just a few of the best Caribbean islands to visit in January, whether you are in search of majestic mountain scenery, rich culture, gourmet cuisine, wild nightlife, or simply that warm, Caribbean sunshine on a picture-postcard white sandy beach.

The best Caribbean islands to visit in January

Rugged scenery in Jamaica

While January might be ‘winter’ in the Caribbean, the heat can still be overbearing at times. For a cooling escape head up into Jamaica’s stunning Blue Mountains – one of the best Caribbean islands to visit in January thanks to its elevated position, offering that idyllic combination of soft breezes and incredible views.

This lush mountain range runs along the eastern edge of Jamaica and offers a fabulous range of hiking opportunities, where you can soak up the majestic scenery and witness a stunning array of flora and fauna. Of course, the Blue Mountains are home to the world-famous Blue Mountain Coffee, which is still made utilising artisan techniques. Many of the coffee plantations offer guided tours where you can view the coffee-making process from bean to cup.

If you’re in search of a place to rest your head the place to stay here is the fabulous Strawberry Hill, frequented by VIPs and celebrities. Just be prepared, getting up to the Blue Mountains entails a hair-raising journey featuring pot-holed roads and hair-pin bends – certainly not for the faint of heart, but most definitely worth it!

Soak up history and culture in Cuba

Scratch the surface and you’ll find that Cuba offers much more than cigars, classic cars, and crumbling architectural grandeur. Rich in culture, Havana is the place to be for anyone who wants to step into another universe, where streets burst with creative energy and historic poignance and friendly locals regularly welcome strangers into their home as part of the Casa Particular accommodation. And with the Christmas’ crowds in Cuba dissipated, you’ll find this is one of the best Caribbean islands to visit in January – post-December is the ideal time to explore this vibrant city.

Enjoy a classic Mojito – a favourite of one of Cuba’s most famous residents, Ernest Hemmingway – and watch the world go by; salsa the night away in a local habanero; or explore Havana’s surprisingly vibrant art scene in Habana Vieja or at the Fabrica de Arte Cubano. 

Feast in the Cayman Islands

January is culinary month in the Cayman Islands, the gastronomic capital of the Caribbean, making this one of the best Caribbean islands to visit in January for foodies.

The gourmet food festival, Cayman Cookout, is held every January on the British Overseas Territory of Grand Cayman, playing host to some of the most renowned chefs and drinks experts in the world. Hosted by the lavish The Ritz-Carlton, Grand Cayman, in partnership with celebrated seafood chef Eric Ripert of New York’s Le Bernardin, this gourmet affair spans four delectable days of barefoot elegance, offering tasting menus, cooking demonstrations, beachside soirees, an extravagant brunch and amateur chef cook-off, and more, all capped-off with the not-to-be-missed gala event.

If this event doesn’t sufficiently tickle your taste buds, then explore Cayman’s myriad world-class fine-dining restaurants boasting fabulous fusion cuisine prepared by award-winning chefs.

Party the night away in the Dominican Republic

Santo Domingo, the capital of the Dominican Republic is the place for hedonistic revellers to flock to. Dominicans love a good party and this Caribbean city has something for every vibe, including bars, lounges, eclectic dance clubs, discos, and casinos where you can try your luck.

Cars crank up their sound systems, playing pulsating beats into the early hours of the morning. Liquor stores double up as meeting points for locals to shoot the breeze and party into the early hours, while salsa, merengue, and reggaeton pulsate from street corners.

Every bar in this thriving nightspot has its designated ‘night’ with happy hour specials and live bands, ensuring a different experience every night. Indeed, Santo Domingo is the best Caribbean island to visit in January for those wishing to let loose – after all, why not start 2020 as you mean to go on?

Be a beach bum in Roatan

Part of the paradisiacal Bay Islands off the coast of Honduras, Roatan is the place to head to in January if you feel like whiling the month away as a beach bum on stunning beaches surrounded by gin-clear waters. The island is as Caribbean as islands come, with a laid-back, anything-goes way of life – perfect if you are someone whose idea of dressing up is donning swimwear and a sarong. Head to West Bay beach, which boasts powder-white sands ideal for soaking up the Caribbean sunshine.

For those that fancy sinking beneath the waves, Roatan offers an astonishing number of dive sites. The entire coastline is fringed by spectacular coral reefs teeming with marine life, making this the place for diving and snorkelling enthusiasts.

For a Robinson Crusoe experience, head to the uninhabited island of Water Cay and spend a day to yourself snoozing under the shade of a swaying palm tree. For one of the best Caribbean islands to visit in January, Roatan is a must.


So, whether you opt to cruise over on your own luxury yacht charter or fly over by commercial jet, there is sure to be an island to suit you. Prepare for an adventure like no other in the Caribbean.

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