When to go
The most popular time for travel to the Caribbean has nothing to do with the weather there. It’s all about the weather elsewhere. From mid-December to mid-April ‘snowbirds’ flee winter in North America and Europe for the balmy climes of the islands.
During this high season, tourism is at its peak and indeed around Christmas, Easter and school holidays some islands simply sell out. Prices spike and places are crowded but its also the time when virtually everything is open.
You can enjoy a dramatically discounted ‘summer’ by visiting the islands during the lengthy low season, mid-April to mid-December. Prices at hotels fall by 40% or more, package deals are common and popular port towns don’t look like a scene from a cattle call. The downside is that some resorts and attractions may simply close and your transport options will be reduced. In addition, the trade winds aren’t as prevalent in summer, so the chance of encountering oppressively muggy weather is higher. Summer is also the hurricane season, particularly bad in August and September, when some hotels, restaurants and shops simply close for the month. If you’re more interested in the culture of the islands as opposed to sleet-avoidance, this can be an ideal time to visit.
The sweet spot for visiting the islands is November and early December. Rates are still low but the weather is good, except possibly where you live, thus giving you one more justification for the trip.
Another impetus for the timing of your trip might be one of the out-sized festivals that are the cultural events of the year on every island.