Here's what I would do in your shoes.
Sail overnight from Tobago to Union Island (St. Vincent & The Grenadines). Clear in at Clifton Harbour and enjoy the Tobago Cays, then up to Bequia. Clear out there and make a long day of it to St. Lucia (Soufriere, Marigot Bay or Rodney Bay are ports
of entry). The passage
from St. Vincent to St. Lucia can be a nasty bash, depending on wind
and currents. Soufriere has the beautiful Pitons and other attractions to see ashore. Fuel
be available in Rodney Bay Lagoon
. (check status of marina rebuild
From Rodney Bay, it's a short hop to Martinique
. Depart St. Pierre for Prince Rupert Bay, Dominica
. Take a couple of days, at least, to see a little of this beautiful, lush, mostly unspoiled island. Martin Carriere (VHF call sign "Providence") is a super guide.
We always stopped at Les Isles des Saintes and Deshaies in Guadeloupe
. Then on to Nevis
(a little gem of an island), St Martin
, and the BVI. Or Antigua
, St. Martin, and BVI.
I've done the island hopping as a delivery
from southern Grenada to Nevis
in nine days, with two lay days. Better is to take 14-15 days minimum for this part of your trip.