Off peak season in the Caribbean is summer and fall, except perhaps Bermuda, which is at a higher latitude and therefore cooler in the summer. As we all know, tropical islands experience hurricanes in the months of July through September. However, shoulder months such as May and June are perfect for travel. There is drizzle but not enough to drench your vacation at the beach. Plus, hotels and resorts drop their rates to almost 60% off.
Most people fly from Florida to islands such as the Bahamas or Jamaica, but flying from island to island is expensive. If you really want to experience the Caribbean from one island to another, your best bet is to take 5-7 day cruises.
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