A week isn't much time to see the area, but here's a suggested bunch of harbors to visit, depending on what the wind
and tide is doing. You need to pay attention to what the tidal current
is doing in Buzzards Bay, Vineyard Sound, and especially Woods and Quicks Hole.
1. Marion to Cuttyhunk, pick up a mooring
in the Pond. Climb to the top of the hill to watch the sunset.
2. Cuttyhunk to Tarpaulin Cove or to Lake Tashmoo (usually can take 6 feet in there at half tide or better). Tarpaulin is a wonderful day stop, though nights can be rolly. I like to anchor in Lake Tashmoo and walk the mile into Vineyard Haven where there are lots of nice shops and restaurants, and a very peaceful anchorage compared to Vineyard Haven or Edgartown.
3. Hadley Harbor is a beautiful spot with some moorings, and what appears to be almost no room to anchor, but I always seem to squeeze in.
4. Woods Hole is interesting, and worth visiting the various museums, etc. Moorings available, and good eats too.
5. Newport is fun, but is really a long haul into the wind unless you happen to get a moderate north wind. Oldport Marine
rents moorings and has launch service
6. Menemsha is very cute, and you feel like you're in a movie
set there. The entrance can be a bit hair raising if there is a strong wind blowing in when the current
is coming out. Very tight little basin with moorings. Nice restaurant there. A trip to the Gay
Head cliffs nearby is worth it.
Personally, if I had a week I would stay within the Marion, Cuttyhunk, Menemsha, Tarpaulin Cove, Lake Tashmoo, Woods Hole, region. Would make a very nice circuit.