Fall (Sept-Dec) Cruising?

[sp543]

I am a college student and have the opportunity to take time off (Late august through December) and would like to use that time to sail solo/liveaboard in the bahamas/keys/somewhere warm where I can kiteboard, spearfish, surf, anything. I know this is hurricane season, how are the winds, weather, and sea states during this period in these areas when there are no tropical storms moving through? Would it be worth the risk or should I look at going elsewhere? Might also look into getting on some boats to do deliveries but this type of thing would be my first choice. Any thoughts on where to go other than the Caribbean region if its not worth it? What about Costa Rica/Panama area? are they also affected by heavy weather during this period? I know Spring would likely be the better season, but unfortunately this is the only period that would fit in my schedule.
Thanks

[RedHerring]

Canary Isles and crew on a boat crossing the Atlantic?

[sp543]

Any suggestions in good places to look/people to get in touch with to possibly get a spot onboard a professionally crewed boat? Have a ton of racing experience in dinghies and big boats but not a lot of blue water/ocean experience and looking to change that.