I have a thought for you, but then I'm a light weight and don't like getting beat up clawing into the wind
. Port Everglades and Freeport
have a number of yacht transports that will take you to St. Thomas for a quick and easy trip. If you show up to the transport ship the week before it leaves, they'll give you half price
, if they are NOT FULL.
Assuming you have time flexibility and you can get a half price
deal, it's cheaper than sailing into the wind, after you consider repairs
, time, food
Now you're there and can look forward to the coast down hill on the way back.