....We like Oak Bluffs, but its a lttle further along. Nantucket is unreasonably expensive for moorings that start at $60 plus tax.
Nantucket is a real haul from Newport and you must negotiate the current through Vineyard Sound, so it seems it would be outside the possible for brokesailor. However, we love it there and its worth the trip, if you have time. The moorings are $75 per night. While I bitch about cost as much as the next guy, that mooring field is incredibly well maintained, including chafe gear, they escort you to your mooring and come by with a full briefing of things to do and how to get around. Then leave behind literature. If any mooring is worth the price, its there.
.....we have uised Cuttyhink as a great stop over, Very pictureaque place....with nothing
We LOVE Cuttyhunk. It isn't much closer than Menemsha, but much better protected compared to being outside at Menemsha and is the stop over to getting to the Vineyard or Nantucket. Inside harbor is highly protected on the mooring. We stay outside, as I think there is a 40 or 50 ft max swing inside. Plus, outside is more private.
Nothing beats ordering a steamer lobster at the top of the dock and bringing them back to the boat for din din. The guy that collect the mooring fee on the outside moorings will get them for you, if you ask. Then the raw bar comes around to each boat and a sunset dinghy back to the dock for ice cream is manadatory!! Other than that, there is indeed nothing there.