The Caribbean cruise season, including the islands of the eastern region, runs year-round, with the greatest number of ships there between October and April — when vessels that spend summers in Europe or Alaska move to the Caribbean for the winter. The high season is January through April, as well as holiday weeks like Thanksgiving, Christmas, New Year, and Easter, when people are eager to escape the winter weather up north to bask in the sun-drenched islands down south. Temperatures are warm and toasty all year, ranging from the mid 70s to the high 80s Fahrenheit. June tends to be the rainiest month, but it rarely rains for an entire day.
Hurricane season in the Caribbean is June 1 through November 30, with the peak months for hurricane activity being September and October. Still, chances are you won’t encounter a drop of rain or a single whitecap. The beauty of traveling by sea is that ships can change course to avoid storms.
If you want to save some money and are OK with the risk of cruising during the hurricane season, then September through early December — before the Christmas rush — are the months to find a deal. You’ll also encounter fewer crowds and fewer families with kids.