Best Caribbean Beach Summer Vacations

If your idea of a splendid vacation is basking on a beach, have we got some destinations for you: Exotic islands with some of the most beautiful beaches in the world that aren’t too far away, so they’re priced right.

See our favorite destinations, and don’t miss our tips on finding cheap flights to the Caribbean at the end.

When to Fly to Caribbean Destinations

Summer is one of the cheapest times to fly to the Caribbean. Another is the dead zone between the Thanksgiving and Christmas/New Year’s holidays. Winter is generally more expensive because – well, you haven’t seen too many reports about Caribbean blizzards, have you? But keep an eye on the Atlantic hurricane season which runs from June 1 – November 30.

And always check for Caribbean airfare specials in our Deals Blog.

Best Caribbean Destinations

These are a few of the cheaper Caribbean destinations. All boast white sandy beaches and plenty of other attractions. If you need help finding the island for you, see the Caribbean Tourism site.

To find cheap flights, click on the destination name (which is followed by its airport code) and we also provide tourism links to local attractions, shopping, dining and hotels.

Note: San Juan, Puerto Rico is usually the cheapest of all Caribbean destinations from the U.S.

Caribbean Wild Cards

These islands can vary from cheaper to less so but these destinations crop up in airline sales from time to time and have been featured in our Deals Blog.

Finding Cheap Flights to the Caribbean

Best airlines: Some carriers regularly feature good deals to the Caribbean including JetBlue and Spirit, as well as American, Frontier and others – but never assume one airline will always have the best prices since this varies. Search for flights on on a comparison site like FareCompare so you know you’re getting the best deal.

Where to fly from: New York and several cities in Florida typically offer the best deals to Caribbean islands but exceptions can and do pop up (the Deals Blog recently noted cheap flights to the Caribbean from Dallas, Indianapolis and Washington, D.C.). Set airfare alerts so you don’t miss the deals.

Follow the rules: Some airlines require a Saturday night stay or that you travel mid-week and if you don’t follow the rules, you will pay more.

Break up your trip:If direct flights are too expensive, look for cheap flights on discount airlines to hubs such as Miami or New York, and fly to your island of choice from there. Be sure to leave more than enough time to change planes, in the event of delays.


Updated: October 21, 2015