When my Beneteau
came out of charter
two years ago, I sailed it from the BVIs back to the U.S., solo from PR on. The only over night sail I did was from PR to DR. I did everything else as day hops.
In addition to the GPS
on board, (No charts
for Bahamas) I brought some paper charts
, one small handheld and downloaded the garmin
app and charts for both iPhone
which only cost $50. I also used "The Gentleman's Guide to Passages South" as my primary guide. It takes a bit more reading to apply it in reverse, but then it's much easier going that way....
I sailed back early Summer. In winter you will have to think a lot more about the effects of cold fronts including the limitations they have for protected anchorages
, especially if you are thinking about sailing along the north coast of the DR.
If you want more information regarding stops, etc. let me know. Happy to post more here or via personal message.