Hiya, I sailed to the vineyard this summer for the first time but from Shelter Island NY. The conditions were fine past Block but windows will vary. I use Pocket Grib on my
iPhone for
wind direction and speed (along with other sources) and
iNavX for
navigation on my
iPad which is really great. It or something like it along with reading any guides should help through areas like Watch Hill. Also a big consideration is the
Race which is the
current in and out of the Sound and Narraganset bay. Highly recommend a copy of The Eldrige for tide and
current information. Check out Cuttyhunk if have a chance and like low key, out of the way places.