A few thoughts on roughly when:
January:
-lotta people are still around from xmas/new years so lots of partying to do
-nicest weather of the year, warm and sunny but with a beautiful breeze
-still tourist season so everything's open
-but that means hotels and stuff aren't doing any cheap deals... more on that later
February:
-weather's still gorgeous
-my birthday at the end of the month w00t!
-super bowl at the beginning of the month w000t!
-still tourist season
March:
-weather's heating up a bit but still a nice breeze
-still tourist season, and gearing up for sailing week, so lots more yachties and parties in the yachtie area
April:
-weather's getting pretty warm, but the water is clearer for snorkelling etc
-sailing week at the end of the month, which is basically a three-week-long party (there's some sailing somewhere in there too, I guess)
-because it's sailing week, hotels etc are booked up way in advance and go for premium rates
May:
-weather's heating up pretty nicely, still a decent breeze
-sailing week over, tourist season is done, restaurants and stuff start closing for the summer (those that close, anyway)
-cheaper accomodation rates start
June:
-hot
-water is beautiful, warm, clear, and calm
-hurricane season starts
-island's kinda dead
-my own vacation tends to start sometime in mid to late June
July:
-really hot
-water stays gorgeous
-people start coming back for summer, partying ensues
-I tend to be away for some of the month (although if we plan far enough in advance, I can always rearrange that if June or July worked particularly well for people)
-hurricane season
August:
-even hotter. breeze starts dying
-everyone's back for summer, lotta partying going on. bars are full every night of the week
-hurricane season
September:
-hottest. no breeze (late August to mid-to-late September is the hottest time of the year)
-everyone's left again, this place is truly a ghost town
-peak of hurricane season
October:
-breeze starts coming back. thank fuck. october starts out pretty warm and ends up gorgeous
-places that closed for summer start opening back up
-cheaper rates may still be had
-still hurricane season, but feels safer than September
November:
-lovely weather. days are pretty nice and nights are beautiful
-hurricane season is over!
-island's back in full swing
December:
-best weather of the year
-probably my favourite time of the year here, actually
-from mid December onwards, everyone comes back to the island for xmas/new years, so the partying is great