Let's start with the basics: The peak time for travel to the Caribbean is, generally speaking, December into April/May. While the region's rainy season technically begins in May, its full impact isn't usually felt until later in the summer, as the heat and humidity rises. (August through October, the heart of hurricane season, see the least visitors.)

There are a few golden months in between, however — May, June and July are often the "shoulder season" or "summer season" — when airfares and room rates begin to drop, coveted resorts are more likely to have availability and the crowds at popular beaches begin to wane... (continue reading)