Generally speaking, Hurricane Season runs from June 1st through November 30th of each year, however in recent years the Caribbean has experienced a few Hurricanes earlier than June 1st, and a few later than November 30th.
So what is the likelihood that a Hurricane will impact your vacation? There’s no way to predict that as far in advance as most people book their trip, but when you consider that in any Hurricane Season there are typically only a few (although 2020 was a record-breaking season, with 12 that made landfall somewhere) and the season spans 5 to 6 months, there’s a lot of time in that window to have a fabulous vacation with great weather. Just no guarantees!
Lots of travelers prefer this time because many resorts offer cheaper rates during Hurricane Season (specifically because of the risk), BUT it’s wise to be sure you have Check Pricestravel insurance that includes trip interruption that specifically includes Hurricanes (so no “act of God” exclusions). The best is (naturally) Cancel For Any Reason insurance (aka “CFAR”) because if a Hurricane looks likely just before you head out for vacation, you can cancel and rebook without losing your deposits or payments, and it also often covers your airfare changes.
While all travel sellers will offer trip insurance at the time you book your trip, you can also (usually) add it yourself through these companies, so it’s worth comparing costs and benefits to be sure you’re getting the right coverage and a good price.