Caribbean can be a bit iffy that time of year - especially northern caribbean as the main hurricane belt goes right across them.
Might be better off going to one of the more southern islands like Barbados or St Lucia as hurricanes rarely pass this area (or at least dont go directly across these islands)
I went to St Lucia for a week last september and weather was excellent - rained once during the night, and for about 10 minutes during one of the days we were there.