All great options. We keep our boat in Mystic and highly recommend it. Lots to do and a nice downtown loaded with restaurants and marinas. If you don't want to deal with the bridges than stay south at Safe Harbor Marina, Mystic Shipyard (my marina), or Mystic River Marina. The first two you can walk to town, or just dinghy up the river. For the more eclectic option go to Mystic Seaport. You get to dock next to all the old tall ships and have access to the Seaport village while its closed. Our favorite place is Block. We are there just about every weekend under anchor. So much to do and the best beaches and swimming water of any of the islands in the area. MV - we like Menemsha the best. Its the quiet side of MV. They have a great marina inside the harbor with the best sunsets on the island. It is an active fishing port, but still very quiet. Great fresh seafood at Larsons; explore Menemsha Pond; Aquinnah beach and Gay Head Light are close; or take an uber to the other side of town. Best beach on MV is East Beach on Chappaquidick IMO. Edgartown is definitely busier, but way nicer than Vineyard Haven or Oak Bluffs. Oak Bluffs is the party scene if thats what your into. Cuttyhunk - Not far from MV at all. If i recall the harbor is only like 7 miles from Menemsha. Like said its a blast from the past. We always stop here for 2 nights. Its a small quiet place so anymore time than a few days might get old fast. We did 4 nights one year and it rained two days. That was too long.... Nantucket - it was our first trip there this year. We reserved a mooring on dockwa. What a cool island. I equate to a bigger version of Block with none of the city feel that you get in parts of MV. Great restaurants, cobblestone streets, fantastic beaches (although a bit rocky once in the water). We will be back. Bring your really big wallet on Nantucket, particularly if you are securing a slip at the boat basin.