I like stopping in Edgartown by boat. We've enjoyed several pleasant visits as a family over the years. This was our first time without kids.
It's the anchorage I enjoy the most. That is, as long as the weather promises, without fail, to blow from the south, only. We've never had a bad night anchored in the open outer harbor, yet.
There's quite a current that runs through but I find it tends to stabilize the boat against the inevitable wakes. You can see a wake from our anchored boat from the strong current. Holding is good and it's shallow.