Probably early summer ... our actual anniversary is in September, but, as you know, not the best time for traveling in the Caribbean We were thinking a pirate wedding on a windjammer ... what do you think?
September could be very exciting! Especially for anyyone who has never been through a Category five Hurricane ...
Early summer or late spring isn't too bad as the temperature doesn't vary much in the Virgin Islands. Also the air fares and hotel rates will be a bit lower than during the winter season. (However, having been in the travel industry, you already know all this.)
Regardless, my advice would be ... the closer you can get your date to the winter season the better. The air is drier (less humidity) and the nights are a litlle cooler.
A Playmofriends Windjammer cruise could be a lot of fun for everyone! We might be able to get a great group rate if we start working on them soon. I wonder how many "friends" might actually be interested in a Playmo-pirate cruise in the Caribbean?