Here's a tentative route for our May drive ( http://goo.gl/maps/xKgBz ). I'm currently looking at May 19; I'm assuming that the following Sunday, on Memorial Day weekend, is going to be difficult for many (and I'll be in Charleston SC). Feedback on the route or dates most welcome.
The route starts just east of downtown Newbury MA at the Joppa Flats Audubon Society facility, which has 2 free Chargepoint chargers. We wind our way down to the south coast of Cape Ann, then follow the coastline through Manchester-by-the-Sea and Gloucester to Rockport. We'll finish up at a private estate in Rockport for refreshments.
Afterwards, I'd recommend continuing counterclockwise around Cape Ann to Annisquam, a pretty town on the water. If you really want to make a day of it, bring your beach things and head over to Wingaersheek Beach, facing Ipswich Bay.