We did the trip from Block to MVI last July. Block to Cuttyhink was a great day sail. Cuttyhunk was great to explore. There are bed and breakfasts to have dinner at, or you can oder cooked lobster during the day and have it ready to take back to the boat for dinner time. I think it's first-come-first-served, no reservations. Fill up with water there, I didn't but heard the glacial water from the water dock is the best.
from Cutty to MVI, we went through an opening in the islands -- I think it might have been Quicks Hole. It was 1 island north of Cuttyhunk. Watch the currents on the east side of that island chain. The tides flow out to the south and in to the west -- solving the mystery of why there were so many shipwrecks there was one of the things that helped launch Eldridge's tide books. There a section in the book describing it.
As you go up to the north between Cuttyhunk and MVI, keep a look out for our propeller. (grin) It fell off somewhere near the NW corner of MVI. It was a nice 3 bladed prop that was just reconditioned by the marina. We really missed it for the next week or so.
We stayed at Edgartown. Wolfie, the dockmaster's son put our new prop on. The pump-out guy -- on his own -- managed to get a stuck fill port open and even lubricated it. really a nice place with people who take care of their visitors. Edgartown has a floating water dock. (Yes, Wolfie laid the pipe for it.)
Block to Cuttyhunk is open water. On the way back, we motor-sailed into 4 foot waves.
out of time.... good luck.
Fun fact #2484: In my avatar, that's DavidPM at the helm of my boat.
Bland, non-political statement goes here.