I'm pretty sure you will wait a long time for wind
changes. Straight shot is a struggle. Get a book by Bruce Van Sant. Very good.
I followed it back in 2006. Basically drop anchor
at Big Sand Cay and wait for the front, if one comes ride it to Luperon. You will most likely motorsail most of the way, but at least you wont be beating into strong trades.
Then coast/motorsail during the night along north shore of DR. You wont make much progress sailing into trades during the day. You can wait at Sosua or rio San Juan
for night lee to set in. The book was on the money
about the trades. Hispaniola is tall and large. At nights it provides emanating land affect wind that kills the trades.
As you get to Mona, you better get well off DR coast by Noon or trades will punish you. Watch for hourglass shoal. And when I arrived I tried checking in by phone
, but she said i have to come in. I thought I would get some rest at Boqueron before taking a cab to check in at Mayagues but woke up to a sound of a off coast guard knocking on my hull
. After the full search and boarding procedure, dogs
and all, I was grateful they let me take a cab ride to check in at mayaguez.