Bermuda
While not technically in the Caribbean, Bermuda has a lush subtropical climate, with warm waves and gentle breezes from the Atlantic Gulf Stream. For a true tropical experience, the time to visit is May through mid-October, when low temperatures fall only to the mid-70s and highs are in the mid-80s. Humidity is high during these summer months. Fall and spring temps hover between the mid-60s and mid-70s, with the most rain falling in October. Winters are mild, with temperatures in the 60s.