I'd make just one suggestion and that would to have all of your hiding spots all picked out before leaving in case you have a storm coming and need to go set up your boat for a storm. TCI (Provo
) has Sellars pond in Turtle Cove. North coast of the DR Has Luperon and further south there are some spots in Bahia
de Samana. I'd chose the south coast of Puerto Rico
because the North coast really doesn't have anywhere to duck into. Ponce and Culebra
both offer hiding spots although Ponce would not be my first choice. St. Thomas is of course a well known hurricane hole with the mangrove lagoon
inside Benner Bay.
The best route to take this trip is to leave Provo and head
straight out into the Atlantic heading towards VG and Tórtola making a single
tack towards STT when closing in on the islands. However, This is a 3-4 day sail depending on wind
conditions, and I would not suggest this route at the height of storm season. I guess if all was clear from Coast of Africa
through the leeward islands
you could go for it, but late August, Sept, they roll off south Africa
one after another So I'd be cautious.
Good luck with your adventure.