I don't know if I can help you at all, but I went to a destination wedding once and it was a great experience for everyone who attended. My close friend's daughter got married. I only knew a few of the wedding party before the wedding, but after days of this group of 50 people meeting up around the island (we were on Maui) to golf, go to the beach and other tourist things in various small groups, everyone got acquainted nicely from both the bride and grooms families. I helped with the wedding a little, what is that saying, "Many hands make light work"? There was a local wedding planner which was a little tricky to set up from a distance but turned out okay as she set up many things in advance, found the property for the wedding, the caterer and other tasks, but we set the tables with fruit and palm frond centerpieces thanks to Costco and other local resources so we could personalize according to the bride's taste (and it turned out beautifully!). The bride had relatives who performed the ceremony. We were at a house right on the ocean.
When I meet up with any of the attendees we still exclaim over that shared experience. As far as I know all the wedding party paid their own costs for the airfare and lodging, but the brides family took the women out for manicures/pedicures and some other special things. Most of the guests arrived at least a week before the wedding and left soon after, so most of the trip was truly a celebration of this wedding. I don't know much about any of the locations you suggested, perhaps some of our FORT friends know something about the climate in those places at that time of year. What about somewhere in Mexico, Belize or Costa Rica? You still may run into issues with hurricane season.
M_shelll, it would be fun to see what other people have done for destination weddings, especially outside the US. I hope you have a great time planning your special day!