So you have also asked where to go and what to do.
I like Edgartown for lunch, and Oak Bluffs for dinner. Oak Bluffs after about 9 turns into a strange party scene, a bunch of non-islander hipsters, and a little "gangster-ish". But I retreat to Lagoon Pond by then, where I've anchored several times...bang a left after the green barrel. I dinghy
to the beach to the east of the bridge, and can walk to Oak Bluffs, or to the beach west of the bridge and walk to Vineyard Haven.
I've had "rock star parking" a couple of times by anchoring
in the Haven between the mooring field and the jetty, which is allowed, and within spitting distance of the dignhy dock
. Ideally this is done during a southerly, with assurance that the wind
won't shift from the N at night, or else you might swing close to the jetty.
If you want, take a scooter around Tashmoo and then you can see what that is all about.
Then scooter to Edgartown for lunch. If you like convenience, and the activity of a mooring field (but not the mayhem of Oak Bluffs), a mooring in Edgartown is the way to go, where you'll get the quintessential Vineyard experience.