Originally Posted by Cheechako
The Gentleman's Guide to Passages South
The book to read to plan this trip.
A quick summary of the main issues.
About the latitude of Florida
you hit the trade
winds. 99% of the time they come from the E or NE or SE but basically east. So if you leave from Florida
to the USVI you are beating dead against the wind
for 1000 miles. So how to deal with, minimize or avoid altogether this issue?
1. If Florida and/or the Bahamas
are on your itinerary then you can island hop from Florida all the way to the VI. You can break up the trip into short legs, max about 150 miles by stopping at all the little islands, DR and PR on the way. This way you can play the weather
and take advantage of the occasional front that gives you fair winds or at least do the windward bashing in short bits and rest up in between.
2. I-65. Leave from north or central Florida and sail as close to east as you can straight out into the Atlantic until you reach 65 W longitude and turn south.
3. Follow the detail instructions in the Gentlemans guide. More or less sail very early, nights, etc to take advantage of the land/sea breeze effect.
4. If you can avoid Florida then go south to NC and sail to Bermuda
. From there it's a relatively easy sail south to the VI.