Re: Marthas Vinyard
You will find Oak Bluffs very crowded and noisy, I am not sure there's any anchoring room, if there is, its not any and even less privacy even on mooring.
You might consider Vineyard Haven it has all the things that make the boating life special in spades, including a lot of swing room. The anchorage area can get unbearable in an eastern blow, so you should consider going into the Vineyard lagoon for the period, the lagoon is quiet, safe and generally empty, and if you want, you can skinny-dip.
Certified...in several regards...