There are many variables in this transit but since this evidently is your first time and with a new boat I would suggest a more conservative approach .
The first leg would be from the BVI to Puerta Plata in the DR. This will be a easy downwind run and enable you to stay as close to land as you are comfortable.
From the DR it's all relatively short hops from one island to the next up through the Turks and Bahamas
until you get to the Gulfstream off the Florida
Believe it or not but that last leg across the Gulfstream could be the most daunting leg of all. I grew up in Miami
and the "Stream" was my backyard. Watch your weather
here. Take my word for it, when the Stream gets snotty it can be some of the most treacherous water
in the world.
Other than that it sounds like a great trip. My advice is to take your time in the Bahamas
. Some really fine cruising up there.
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