We just returned from the Vineyard and here are my thoughts:
We spent two nights anchored in Lake Tashmoo, it was quite crowded over the weekend. About a 20 minute walk into Vineyard Haven where you can get a bus that will take you to different island locations, for $7.00 you can ride the bus all day. Tashmoo has a free pump out boat ($5.00 tip suggested), fresh water is available at the town dock where you can tie up your dinghy. No fuel available.
Oak Bluffs does not allow anchoring in the harbor, mooring fee is $40.00 per night. Mandatory rafting of boats, up to 4 on each mooring when it is busy. This is what I saw Sat and Sun, I could just imagine drunks climbing over my boat at 1:00 a.m. so we stayed in Tashmoo. Slips are $3.00 per foot minimum 30' plus electricity. The slips are right against the sidewalks with each one having a ladder you have to climb up and down. You could have a thousand people looking down into your boat on a weekend. As others stated this is the party town on the Island.
Monday we did move to Oak Bluffs as this is where relatives were renting a home for the week and we had a mooring to ourselves. There is also a launch service for $6.00 round trip. Diesel is available in the harbor. Nancy' Restaurant on the waterfront is a bit pricey but the food was excellent. Giordano's in town has good Italian food, Mad Martha's for homemade ice cream.
The Lagoon is a wide body of water and could be uncomfortable at anchor if it is windy. There is a bridge to deal with, not sure of the clearance and the opening schedule. Quite a long dinghy ride over to Vineyard Haven.
We went by car to Memensha where I spoke to the harbormaster. They have limited dockage but there is good anchorage outside the harbor depending on the wind direction. This is an old time quaint New England fishing village. There are two fish markets selling cooked seafood, this is the cheapest place for a lobster roll that I saw on the Island, at 10:30am I just had to have one.
Edgartown is extremely crowded, hard to find a parking spot, you can shop till top you drop here. Luckily we couldn't park anywhere so the Mrs just did some ride by shopping.
We will definitely go back and spend more time in the area in the future.