Choose your island wisely. Airfare is one of the key expenses of any Caribbean trip, and some islands are much easier — and cheaper — to get to than others. For the lowest fares from the U.S., look for destinations served by low-cost carriers such as JetBlue (Nassau, Montego Bay, Barbados) and Spirit (Aruba, San Juan). Keep in mind that more competition usually leads to lower fares; you’ll pay less to fly to Jamaica, which is served by dozens of airlines, than you will to fly to an island like Dominica, which only has a handful of connecting flights on American and JetBlue.
