Craig, we've made two-week cruises from Buzzards Bay six times, hitting some old spots and new ones each time. This link will take you down to the page for all of them: http://www.sailonset.com/SailingNE.html . We always debate the overnight time-saver and also the leave-the-boat that you are considering. Rockland is a great spot with all the services you can want, including land transportation. What plans have you made for leaving your boat? I'll again suggest Charlie at Beggars Wharf, who has close-in moorings and isn't far from about anything.