Glenn Ashmore wrote:

The FIRST book you should get is Bruce Van Sant's "Gentlemen's Guide to
Passages South". Very detailed instructions for a liesurly island
hopping sail down the thorny path. Suggestions on routes, good
anchrages, staging points, places to reprovision and most important, how
to watch for windows. Begining to get a little dated because it was
written before all the new weather info sources became available but the
stratigy is still sound.

He has a new one, but I was disappointed in it because it is mostly a
rehash of the first one.

The second book is David Jones' "The Concise Guide to Caribbean
Weather". A treasure chest of weather patterns and signs to watch for.

For easy reading about the Caribbean cruising lifestyle with some
excellent detailed information are Bill Robinson's "A Winter in the Sun"
and Anne Vanderhoof's "An Embarrassment of Mangoes".

sea_faring wrote:
Request for information..

Assume boat is ready, crew is competent and prepared. ( I say this to
focus on the items listed below)

Plan is a 1 year passage from Florida into the Caribbean (Windward
Islands)
Is anyone aware of good references on passage planning for such a
trip?
Perhaps there are some good books/sites of cruising logs of such a
voyage….
Currents, weather windows, customs issues, etc?

You might also try some of the Pardey's books, such as the Cost
Conscious Cruiser and she's written one on provisioning.
grandma Rosalie