We went to Tashmoo after Cuttyhunk and stayed in Tashmoo 2 nights on the hook. It blew pretty strong the first night, and we set our anchor well. Walked to Vineyard Haven the next day and rented a car from Hertz for 24 hours. The Hertz guy was really nice to deal with -- a good experience, and we got a new car with only about 700 miles on it for about $100 including all the fees/taxes. Makes provisioning much easier and we got to visit some of the other island towns, restaurants and events out of the town-centers (went to a crafts fair at an arts center that was pretty neat). Stopped at Cronigs Market for the first time - it was an experience -- like Whole Foods (a.k.a. Whole Wallet) but much more expensive (if that's possible). $6 for ONE avocado! Yes not a typo. They had some nice specialty foods but needless to say we bought avocados elsewhere.
Where did you stay in Vineyard Haven? How long were you there?