That's good information, capta. I've wondered about going west from Florida. Some of the western Caribbean ports look interesting, but it seems everywhere is uphill, against the wind and/or current. And, that way has some long passages. So, starting from Florida and the Bahamas as with most people it seems the best course is to prepare to beat upwind until St Martin.
Single-handed doesn't seem to be too difficult, in the right weather for one long night, but I doubt I could manage more than 30 hrs without good sleep. Rough seas can be tiring, and hard on
autopilots, but again good preparation and good equipment should make the difference.
How reliable are
radar proximity
alarms? Is ship traffic much of a problem from Bahamas, through Mona passage and the route from VI to St Martin.
With
autopilot set to follow the wind I could use
GPS alarm if there is a wind change. But, of course, using
autopilot would require lots of battery power and re-charging capabilities. A wind speed alarm would not give you advanced warning of a squal, but still it would be a help. Also, as you say, keep minimal sail set - keep one reef in the main - or, better yet, get mast
furling and buy a new main sail. There never seems to be enough money to do it all...