All good recommendations, plus...
Don't forget the U.S. Coast Pilot, Books #1 & 2, for New England. And, I've found the AAA tour books and other land-side sources helpful supplements for finding restaurants, attractions, etc ashore.Marblehead & Salem, MA are interesting towns to visit. The waters of Salem Sound are bounded by a number of islands that make it an interesting stop along the way up from Boston (about 25 miles). Easier anchorages found in Salem Harbor, as old Mblhd harbor is pretty crowded in the summer. Gloucester is about 12 miles away to the east & is another good harbor. From there north, other than Newburyport, MA & Portsmouth, NH, there aren't too many great dirty weather harbors to get into until you get to Casco Bay. Most of the harbors along the southern Maine shore are small, with narrow entrances exposed to the weather on the Gulf of Maine. Local knowledge helps with negotiating them -- a call to the local harbormaster is advised.If you plan on visiting Casco Bay, I found Quahog Bay, tucked inside Sebascodegan Island at the north end of Casco, to be a truly great anchorage. It's listed in the Taft book. The city of Portland was interesting to visit -- lots of maritime activity and a nice restoration of the downtown area -- as was South Freeport (get your L.L.Bean "fix" in Freeport, a short taxi ride away; also, there's a nice general store in the village that serves breakfast).Penobscot Bay & the adjoining waters (Jericho Bay, etc. to the north) are truly the greatest cruising ground you'll find on the East Coast. Hundreds of islands, many historic towns, wildlife, windjammers, etc. We cruised Penobscot Bay for a whole week and barely made a dent in the must-see list.Obviously, this note can't do justice to all the spots along your route.--Ron