You can also anchor outside the mooring field in Vineyard Haven, which we preferred as a base. We used our Whaler a lot. The Vineyard is very busy that time of year, every bit or more so than Block. We preferred picking up a mooring if we could. There is a very comprehensive bus system that serves the island. Another spot to consider is on the south side, Mememsha. No anchoring in the harbor, but in then right weather you can anchor off the beach; very pretty and laid back. On the way to and fro, spend a day or two at Cuttyhunk for an even more laid back scene, (mooring or anchor outside). Anchor in Tarpaulin Cove for a more wilderness type anchorage, and Hadley Harbor (often crowded) for a protected sylvan setting.
"There's the Right Way, the Wrong Way, and what some guy says he's gotten away with"