Having spent several nights over the years anchored in the Menemsha Bight, I can say that I would not want to do so again, with winds from any direction! Rolly-polly is how I would describe it, and very unpleasant! If no mooring is available inside (used to be 3 boats to a mooring), I move on to Tashmoo or Vineyard Haven. Well worth the extra traveling to get to a peaceful anchorage! Menemsha certainly is a great stop, though, and I too have ventured up into the pond by dink, and would not take the big boat up there!(draft 6 ft). Menemsha is a good temporary anchorage if you want to wait for a fair tide to continue up Vineyard Sound. You can dink in, either eat ashore or take out great seafood. Then be ready to catch a fair tide up the Sound. Just my 2cents!