welcome to the neighborhood
You have a good plan.
IMO the best ways into Vineyard sound are either through Quicks Hole or between Cuttyhunk and the Vineyard when arriving from the west. Avoid Robinson's hole (it's doable, but a little tricky), and if you want to do Woods Hole do it at slack in a sailboat. My friends that run local marina's will not like this advice because Woods Hole brings them a broken boat that got washed up on the rocks at least once a week in the summer (good business). Get good tide tables. Try to time your passages through Vineyard Sound to go with the tide, this will elevate your speed a couple of knots (or vice versa if you don't).
I like Cuttyhunk best. It reminds me of Maine. Another nice overnight anchorage is Tarpaulin Cove, assuming normal summer conditions with a W in the wind direction. The outside of Menemsha should be fine too in normal summer winds. Inside, they have very little space in a small basin.
Vineyard Haven is fun, watch the ferry traffic and the people. Lots of moorings available outside the breakwater, and lots of room to anchor.
Oak Bluffs in more the party town. Prepare to get rafted up on moorings or take a slip with people walking buy your boat to the wee hours. If you want peace and quite, don't go.
Edgartown is also very nice. We like to anchor outside the harbor in settled conditions. There's a lot of current now in the harbor since the breach on the south side opened up.
I think I remember Block to Cuttyhunk as around 40 km. In prevailing SW this can be a nice sail. Be sure to find the guys with the raw bar boat in the evening. Great stuff.