I just came back from sailing to Maine
We sailed to Penobscot Bay, up the Bagaduce River past Castine.
We also drove down the coast to Camden Maine where I spent an hour looking at the old schooner fleet there.
If I were in your boat shoes, I would do some online research
into taking a sail on one of the schooners. I think that could be especially memorable.
Also, while there the winds were light, so conditions may mean little actual sailing. Of course that changes, but I would not necessarily depend on strictly sailing.