What a great topic Tom. I too have made this trip and return from Pt. Judith to Boothbay or Camden about 9 times over the years and once the reverse when I lived in Maine. The early trips were aboard my yawl Silverheels and we usually sailed direct from Pt. Judith and arrived the second morning. We usually had the prevailing southerly and had great sails. Transiting the canal on the midnight watch, nights on the GOM, whales and porpoises, very little traffic, great fun. The most recent trips with my Hunter 44 have been entirely harbor hopping with no overnights. We usually have gone Cuttyhunk, Red Brook or Sandwich, Scituate, Gloucester or Little Harbor, Wood Island or Portland, then Boothbay, 5 Islands, or some other harbor in that area. as you say, those trips take about a week with a day here or there for bad weather. These trips have featured very little sailing also, as the time of day when underway typically does not have the best breeze. Also it has certainly been my experience that the further NE you go, the less wind you have period. Once north of Buzzards Bay we usually find light winds on the perfect summer days we all like. Now the trips back. Overwhelmingly we have found little of no wind to sail on the return trips back to Pt. Judith, with a few exceptions. I can remember nice sails off the New Hampshire coast, Cape Cod Bay, and of course Buzzards. A few times we waited for a nice NW breeze after a frontal passage. But generally speaking, our sailing percentage vice powering or motorsailing which we usually do is around 10-25%. 50% is an unqualified success. The big difference is that in the early trips I was working as you are and I was limited to 2-3 weeks, which as you say is the absolute minimum, and 2 weeks is really tough. Now being retired time is not an issue so we can explore harbors, stay over a day or two, when before we always had "get there itis". There's really no silver bullet as such unless you have the flexibility to wait for the perfect breeze, northerly or southerly. The route I usually take only adds about 15 miles to the rhumbline distance from the canal to Boothbay, and the crew enjoys the trip a lot more when every night is a good night's sleep. There are other stops along the way as well such as York, ME, Plymouth, MA, P-town as you did, Boston Harbor, Casco Bay, and so forth. But I have to say the key is time and flexibility. Then of course, one could spend an entire summer doing the Maine Coast, or the islands, RI, LI Sound, and so forth.