CARIBBEAN TIP: TAKE A NON-STOP
One flight to the islands can save you money. So find out if an island has nonstop service from a major U.S. hub such as New York, Atlanta or Miami. If so, it's a reasonable bet that it ranks as an affordable paradise. After all, it's cheaper to pay for one flight to an island than two. For example, I recently flew to Puerto Rico for $325 round-trip on JetBlue; then I had to add on the price of my connecting flight to the BVI’s, an additional $234. Plus, nonstop service eliminates the potential hassles and delays of a connecting flight.
The major islands that have nonstop flights include Jamaica, St. Thomas and Puerto Rico. Larger destinations, such as the Dominican Republic, offer flights to more than one city. All of these islands have lots of resort hotels, condos and villas for rent, and because that large bed base needs to be filled, these are the places where you'll find the greatest selection of last minute packages and deals.
The smaller islands that get some nonstop flights are Aruba, Grand Cayman, Bonaire, Grenada, St. Kitts, St. Lucia and Trinidad. But keep in mind that those flights may be weekly or thrice weekly. Delta, for instance, serves Bonaire once a week from Atlanta. And while service to the smaller islands is in place as I write this, it will be the first to go should the airlines decide that a route is no longer financially feasible.
Apart from the usual suspects such as Orbitz, Expedia, et al, there's no source for discounted flights to the Caribbean. If you want to find deals, focus on low (summer) and shoulder (spring and fall through mid-December) seasons. But do keep a weather eye on hurricanes, which occur from June through mid-November. And for those who haven't gotten it together to either obtain or renew a passport, remember you don't need one to visit St. Thomas, USVI or San Juan.