Bitter cold got you down? Wondering which island will satisfy your deepest longings for warmth and fun? We’ve partnered with Caribbean getaways expert Angie Orth from Angie Away to share a few suggestions to inspire your winter island daydreams.

It comes as no surprise that nothing draws my thoughts toward the Caribbean more than wintertime. And that’s hilarious, because I’m based in Florida, where one or two flurries is the equivalent of a blizzard! I don’t know how my friends up North manage the snow and the cold year after year. Either way, whether you’re actually cold or just “Florida cold” like me, it’s that time of year when we all set our sights on balmy, beachy dots on the map. Any place with a warm, salty breeze and an umbrella drink, right?

The Caribbean has been through one of the worst hurricane seasons in history, but most of the islands, resorts and cruise ports are open for business. So which beach getaway should you choose to warm up? I’ve got tips!


Bahamas - Where to Go in the Caribbean

St. Kitts is a gorgeous island with lots to do, and much more to entice families than you might expect! Home to the Last Railway in the West Indies, kids love the 18-mile train journey back in time. It’s a treat to kick back and take in volcanic peaks, old churches, abandoned sugar mills and epic views over the course of a few relaxing hours. Tropical drinks and warm sea breezes are included in the rate. Kids will love the eco-tours near the volcano, which often include spontaneous interactions with local Vervet monkeys.

Adventure Lovers

Adventures in Bonaire - Angie Away

This is a tough call, because there’s so much to do around the Caribbean islands. But if I had to choose one, I’d say Bonaire. Renowned for scuba diving, you’d be forgiven if that was the only adventure activity on your itinerary. But there’s so much more! Cave snorkeling, windsurfing, high speed Twizy cars and deep sea fishing are just a few of the offerings. Bonaire is off the beaten path but so worth the diversion.

Beach Bums

Aruba - Angie Away

Though I’ve never been able to master the art of sitting around on a beach myself, I know many folks whose idea of bliss is finding a lounge chair and occupying that real estate for 7 days in a row. Someday, I aspire to try it! In the meantime, for those of you who are already experts, I recommend Aruba, a sunny, friendly island ringed with white sand beaches, clear, calm water and casual resorts.

Photographers & Instagrammers


If shooting the perfect Instagram photo is on your must-have vacation bucket list, Cuba is a perfect place to visit. Havana juxtaposes history and turquoise seas in the most photogenic of ways. Hire a classic convertible to cruise you around the coast for the day. You’ll have hundreds of unique photos by the end of the day. If you want to escape the cold and step into history, Cuba is worth a look.


Things to do in Saint Lucia

Need a break for just the two of you? My husband and I visited St. Lucia in 2017 and found it to be exactly as advertised: private, relaxing and absolutely gorgeous. We mixed up our stay at Ladera Resort and Jade Mountain, both featuring the breathtaking views you can only get from a room with three walls. We hiked to the top of one of the Pitons and snorkeled in the secluded cove in between them. St. Lucia has a reputation for romance, and I can tell you, it’s well deserved!


Ladera Food - St. Lucia - Angie Away

The food scene across the Caribbean has exploded in the past decade, so if it’s been a while since your last visit, or if you’ve only stepped foot in touristy cruise ports, you really must book a trip and make lots of dinner reservations. I can’t choose just one island with the best food, but I can offer a hint: eat what the locals eat! Start with the freshest seafood – spiny lobster, grouper, conch, mahi – and seasonal produce like mangoes, bananas and papaya. Now that my mouth is watering, I’m going to go book a trip! See you there?

Travelocity compensates authors for their writings appearing on this site; such compensation may include travel and other costs.

Pin It on Pinterest