Is it me? Maybe...
Don, I beg to differ on Nantucket! I have sailed to Nantucket and moored there every other year over the last 8 years. Nantucket has the MOST EXPENSIVE, and most restrictive moorings in the area! How can you say relatively inexpensive?
Nantucket Moorings is the sole operator, charing $60 per night plus 5% tax (the only guys in the area who add the tax, by the way), with a two night minimum, three nights during peak periods. Tough cancellation policy - don't expect to get any of your paid-in-advance money back if you can't make it or leave early. Fuel is very expensive there, too.
On the other hand, Edgartown is $40. Right, that's 2/3 of Nantucket, and no minimum stay (two day max. on first-come moorings, two week per month on reserved moorings). Cuttyhunk was $35 last time I was there.
In Newport, there is plenty of room to anchor, but it can be deep, so bring a lot of anchor line. Block is great for anchoring, big field, shallow, sandy bottom. Anchoring is free.
Vineyard Haven is dry, and the restaurants there are expensive, apparently making up the lost alcohol revenues on the food prices. You can bring your own, but some restaurants charge as much as $15 "corking fees." Rip-off. Couldn't get a mooring when I went, and no place to anchor in the inner harbor. Anchored out, lousy ride with ferry and freighter wakes seemingly all night.
Edgartown is my favorite. Anchor outside the harbor, free, close to town dock with free showers, close to the beach, also served hourly by the launch. Or, anchor in Katama Bay, South of town, longer dinghy ride and a launch up-charge, but the best place if its blowing from the North or Northwest. Lots of bars, restaurants, shops, Edgartown Yacht Club.