Cheapest Caribbean Islands to Visit in the Winter

Escaping the cold weather is a must - especially when the temperature starts to look like my shoe size. Below is a list of the 8 cheapest Caribbean islands to visit in the winter (from the midwestern United States).

8. Turks + Caicos

Turks + Caicos is a good go-to for those looking for a balance between luxury and affordable. You'll get the turquoise waters, white sands, and unbelievably gorgeous all-inclusive resorts without paying an arm and a leg.

7. Jamaica

Montego Bay and Ocho Rios will be your best bets for a cheap winter vacation in Jamaica. If you're looking for a laid-back, relaxation-focused vacation, this is your spot. Currently, there are travel advisories out for Jamaica, so you'll want to read those before planning your vacation.

6. Barbados

Beaches, shopping, warm and sunny weather every day... do I really need to keep going? With the west side, you'll find a more luxurious, relaxing stay. Whereas, on the east side, you'll find yourself running into more surfers.

5. Curacao

Any fans of scuba diving will want to find their way to Curacao. It's not as frequently travelled as some of the other Caribbean islands, which means the wildlife hasn't been as damaged. With over 80 dives and high visibility in the water, it's a great place for experienced divers. Also, the airport in Curacao is huge and has tons of flights going in and out everyday, which means the flights tend to be cheaper.

4. Martinique

Martinique has a good balance of beaches and rain forests, and the weather's consistently warm. There are plenty of budget hotels on the island, and both food and entertainment are generally affordable. For an example, local breakfast is anywhere from $1.75 - $7.00 USD.

3. Costa Rica

Costa Rica is another popular travel destination for US travelers. There's plenty of budget hotels and according to Expert Vagabond, some backpackers survive off of $30-$50 USD a day. Costa Rica remains a popular choice because it has the beaches, the adventure, the wildlife, the mountains, the culture, the weather, and still fits the budget.

2. Bahamas

The Bahamas are one of the closest islands to the United States, which makes the plane tickets a bit cheaper. It's a popular tourist destination, so there's many affordable resort options and deals pop up all the time.

1. Puerto Rico

Puerto Rico doesn't have many all inclusive resorts, but it's got a boatload of affordable hotels. It's not far from the US coastline and it's a US territory so citizens don't have to worry about getting a passport.


Honorable Mention: Aruba

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