Making a decision when to go to the Caribbean may seem far from easy, especially if you take weather, crowds, special events, and fluctuating prices into consideration. If you dream of spending your family vacation at a Caribbean resort but don't want the usual high prices, think about booking an off-season stay in the late spring, summer, or fall. It is often possible to find some great Caribbean vacation packages during the warmer months, since this is the time when tropical storms could occur more often and fewer travelers visit the islands as a result.