Buying used: If you're not working with any broker, try Doug Weber 508-563-7136 at Kingman marine in Bourne (Cataumet). The Cape has a huge inventory of boats, but more importantly Doug is like a walking University of Sailing knowledge, from inspections to free advice, he has saved me thousands of dollars. Even long after purchase.
It's a great sail from the canal to Boston, prevailing SW wind, sailing through the harbor islands. Doug can also walk you through the decision process. The tall ships are coming to Boston July 8th, so hopefully we'll see you out there.