Depends what you want:
Quiet: Tarpaulin, Tashmoo, Hadleys (get there early), Menemsha
Tiny Town/Maine-ish raw bar service on your mooring: Cuttyhunk
Tie up and Shop: Falmouth---call the harbormaster NOW, not sure you'll get in.
Eat: Vineyard Haven-Black Dog for breakfast
Redbrook/Kingman Marina -Chart Room
Rich and Famous: Edgartown (we call it Ego town here).
Disney meets New England: Nantucket
Noise/crowds/party/raft up moorings/bars: Oak Bluffs
Time the tides in Vineyard and Nantucket Sounds..a couple of knots. Watch out for Woods Hole, it's a honey pot for the local marina's and salvage operators. Quicks is easier...and well, quick.
I'm not worried about you getting caught in any weather, rumor has it you seek out the bad stuff