I know that entire area like the back of my hand having sailed there for 40 years. I’m not interested in joining you, because even though I now live in OR, I can sail there with friends for free. But, my purpose for responding is to warn you off
Nantucket. Here’s why, Too freekin’ expensive! That is, IF you can get a
mooring. I would plan to stop in Block Island (New Hahbah) then Cuttyhunk, maybe ovah to Menemsha, an afternoon in Tarpaulin Cove on the Vineyid Sound side of Naushon, (if conditions allow NO SE wind) then Vineyid Haven and maybe Edgahtown. From theyah you could sail by Cape Pogue, through the Muskegon Channel and back to
Newport, depending on the weathah.
Other places to consider (again depending on the weathah) are
ports in Buzzards Bay. like Mattapoisett, New Bedford, Marion, Hadley’s Hahbah, Woods Hole (you haven’t lived till you’ve navigated through Wood’s Hole Passage) and Quisset Hahbah. If the
wind is nor’wes for a day or so, you can broad reach into Buzzards Bay and sail along the north shore stopping at points along the way. If it then backs to the sou’wes (prevailing
wind in BB, you can close reach across to Woods Hole and then to the Vineyid. Lots of things and places to see without getting screwed in Nantucket.