On MV the best anchorage to pick up supplies is not the quietest.
Anchor just outside the channel south of the breakwater as you enter Vineyard Haven. The area has about 6-7 feet of
water and good holding, though there are usually
boats there. You can
dinghy to the free
dock just north of the
ferry terminal and Stop & Shop is just across the street. All the downtown shops and restaurants are within a few blocks. West
Marine is a short walk down Beach Road heading towards Oak Bluffs. After you're done supplying you might want to move inside nearby
Lagoon Pond for many nice
anchorages. You can
dinghy ashore at the end of many streets--just look for a bunch of dinghies left on the shore. The bridge into
Lagoon Pond has a very restricted schedule, so you have to plan around that. Plenty of
current in the channel, so the ideal is to enter with the
current against you so you aren't being drawn toward the bridge while it is opening (very slowly). There are nice
anchorages on MV off the beach just to the southwest of the Menemsha entrance channel, with only a few restaurants and shops ashore. Tashmoo no longer allows
anchoring. Edgartown you can
anchor just north of Chappaquiddick Beach for the night if the
wind is in the south.
https://sailmv.org/?s=tashmoo