The most proper time to visit the Caribbean is not a matter of the weather there, but the weather elsewhere. Even the ‘snowbirds’ will rush to the Caribbean to enjoy the balmy climes comparing with the winter in North America and Europe from mid-December to mid-April.
Tourism arrives its peak during the very season, some islands are just at the full strength during Christmas, Easter and school holidays. Despite the high price and the crowd, this is the time that virtually every place is open.
On the other side, you can only get a greatly discounted ‘summer’ if you visit the islands in the low season from mid-April to mid-December. Although the hotels will offer a 40% discount or more, the popular port towns are no longer scenes from the Cattle Call. A few of resorts and attractions would simply close leaving you have few options to transport. Moreover, the trade winds here aren’t as common as else places in summer. As a result, the chance of suffering a sweltering muggy weather is higher. Summer is the hurricane season, too. In the worst August and September, many hotels, restaurants and stores will close. So if you are looking for the sleet-avoidance culture of the islands, this is the perfect time to visit.
The psychological moment will be in November and early December. The weather is fine and the prices are not too high. Another factor that influence your time choice could be the many out-sized festivals on the islands, each can be a good reason for your trip.