Blue...OK...the thorny path it is. First the route...without the travel guide notes!....
1. You can do a combination of Coastal and ICW sailing out of Charleston till you get to southern FL. (Dodge Guide to SE US Inlets is an invaluable resource as is Skipper Bob's guide to ICW anchorages and the Maptech Chartbook)
2. Depending on your time...you can cross either to the Abacos from West Palm Beach...then work your way down to Eleuthra and the Exumas. Or...you can head from the Miami area to Bimini and then the Exumas.
3. Once in the Exumas you work your way down to Georgetown (Chicken Harbor) and stage for departure down island.
4. From there you can island hop down Rum Cay, Long Island, Cat Island etc. or just keep sailing till you get to the Turks and Caicos. Providencials there is the main harbor for provisioning, fuel, marinas but adds 50 miles to your next leg so it is better to anchor in the south part of the island if you don't need supplies.
5. From Turks and Caicos you have an overnighter to Luperon in the Dominican Republic. You need a good forcast for this run as you will be hard on the wind and you need to fetch Luperon or you'll end up in Haiti!
6. The most difficult part of the trip is next...EAST for several hundred miles into the trade winds and seas and through the Mona passage to the south shore of Puerto Rico. Van Sant provides interim stops in the DR but in any case you may need to wait an extended time in Luperon till the wind lets up enough to make easterly progress.
7. Once you'v made it past the Mona, I'd suggest a stop in Ponce PR
on the south shore which has everything you'll need and is PR
's 2nd largest city.
8. From Ponce you can make it in a day to the Spanish Virgin Islands (Culebra etc.) or you can do an overnighter and be in the BVI's (or St.Thomas or St. John if those appeal to you).
9. Stage at North Sound in Virgin Gorda for your next leg which is SOUTH finally to St. Martin. It is only an 80 mile sail but seas, currents and winds always seem to combine to make it a rough passage...like a super-surgilator agitator! You can anchor in the Lagoon at Phillipsburg and the hard parts are over.
10. From there you can day sail island to island and on to Dominica.
Hope that is helpful. Next installment...equipment and charts chartbooks...what do you have on the boat now in terms of electronics and safety gear?
Start reading this on line to get an idea of what you'll find along the way and CURRENT info. Good place to advertise your bar too!