[Updated 2018] Now that summer has officially arrived, so has hurricane season in the Caribbean, lasting from June through November, affecting tourists and residents from the Southern Caribbean, and on north to the coast of Maine. Should that stop you from booking a Caribbean or New England cruise in late summer or fall? No, and here’s why. Caribbean cruise rates are never better than they are in fall, especially from late August through mid-December. Crowds diminish, the kids are back