I've done it both ways, i.e., sailed over to the Bahamas from Florida or flown in and then start sailing. It mostly depends on how much time you have and where you want to go. Remember that if you sail over from FL, you've got to sail back. I have run into some nasty Gulf Stream weather on return trips. I've only flown into the BVI and then chartered there. Sunsail, Moorings, and private charters have all worked out well for me. When going to the BVI, I have sometimes packed cooked frozen chicken and other goodies and taken them with me as a provisioned charter can be costly. I've sailed in the Bahamas in mid-winter and found it coldish there. Mid-summer in either location is hot. Be prepared with lots of sunscreen, broad brimmed hats, long sleeve shrits, etc. I've had some of the best sailing in my life at both locations: wind and water are mostly perfect almost all the time (hurricanes notwithstanding....).
