Everything Phil said is spot on correct. That's the fastest and easiest route. As he said, a preventer is essential, you will have prevailing trades as well as the current behind you, we frequently hit 12-14 kt and were surfing down waves.
From St Martin
to the DR, you will have many options for stopping. After that, Haiti
is generally considered to be unsafe, and if you are a US citizen, Cuba is probably still off limits except in an emergency
, so your long leg is DR to FL. You can clear in in Miami
or Key West; if you clear into Miami, you can take the ICW
the rest of the way around (there are a few places where MLLW controlling depth
is about 5.5 feet). But there is no problem crossing the Gulf Stream anywhere between Cuba and FL, it doesn't really start to accelerate until it turns northerly.
Last trip through there it took us 2 days from Tortola to Luperon (where we sat for 4 days waiting for a cold front to pass), then 5 days/4 night to Miami.
Documentation is all the normal stuff... You don't really need a guide book. this is all pretty simple stuff. Just make a list of places you can tuck in along the way (check ActiveCaptain), and make a good dash from DR to FL.
is spotty except in major ports
It's a fun trip! The only caveat is that a hurricane
can form right on top of you with little notice, so some weather
routing might be something to consider.
Best wishes! Pete