Larry,
I always dreamed of the overnight shoot to Maine. Put a lot more Pen Bay time into a two week cruise! Our sailing partners have never been interested, and they've been doing it for over two decades. Finally we made an overnight run in a friend's Sabre a couple of summers ago. We sailed 18 hours on one tack with all the stars to guide us. Awesome! But we found the on-and-off sleep pattern to be less fun. So we shall stick to our old harbor-hopping ways. If you have the crew to help (and then be discarded) it may be worth a try. Tom arrived after an overnight down with his two kids, all relaxed and refreshed. But then he's Young!

You do want to avoid unnecessary time-outs (unless you have time), so it's important to choose stops that don't require detours. P'town, for example, looks right on the rumb line, but in fact is a long loop in and out. Isles of Shoals is right in the way and Jewell Island lets you skim Casco Bay.

Our web pages (see link) have the harbors passed through since we've been doing this this century.