Matt --
If you are contemplating a trip like that there is a good bit of information out there on it. It even has a name -- "Down East Circle Route" which is also the name of Cheryl Barr's book on that route. Full title is "A Complete Cruising Guide to the Down East Circle Route." Book is worth getting for reading through carefully on cold winter nights and dreaming. The entire trip, Statue of Liberty to Statue of Liberty or in your case, Boston to Boston is 2,460nm and she shows it in 45 travel days of 60nm/day. Clearly, with your boat, it would take less. I think the trick would be to go slow through the interesting parts, especially those that are far away and that you won't likely get back to and go faster through the areas that you can easily get back to again like Maine. The other great resource on this cruise is the blog of Celebrate, a Selene 53 that did the trip covered in their 2004 logs. This is a well written blog with some superb pictures including one of nesting gannets that I just love. Heck, some of the scenery is every bit as fascinating as the scenery in the Pacific NW. After the owners completed the trip, they came back ashore and re-entered the work world as the Anapolis, MD based Selene dealers.
http://www.celebratecruising.com/index.htm
The other approach to a trip like this would be to trailer or better yet have your boat professionally hauled to Lake Champlain and then head north and east from there returning to Massachuestts by water. Go back some other time and do the upper St. Lawrence and the Erie Canal and the Hudson coming home that time counterclockwise.
The other thing about the Down East Circle Cruise is that large parts of it can be reached by trailer. For example, in "Great Loop Side Trips" by Ron & Eva Stob, one chapter is on the St. Lawrence Seaway including a trip up the Saguenay River, a fjiord on the north side of the St. Lawrence that is at a longitude that is a little west of the pointy northernmost tip of Maine.
All in all, plenty to think and dream about.
