It might be worth your time considering the Trailer Sailors ( http://www.trailersailors.org/ ) cruise of the North Channel. If you launched in Tobermory, or took the (less expensive) ferry over to Manatoulin Island, you could join the group at any point, spend the time you wanted, and then pull out on your schedule. Very flexible group with a large enough number of boats that you can almost always find someone to go off on a side trip if you want, and a wonderful cruising area.
There is also an active group in your area called the New England Trailer Sailors ( http://www.ne-ts.com/ ). I've never sailed with them, but I've heard good things.
Thanks Jim. The only thing I found on the trailer sailors website is a (very) brief on this years' North Channel cruise, and Mapquest searches of both Tobermory and Manatoulin camp up blank. Do you have any further info?
I belong to NE-TS (used to be MOANE, MacGregor Owners of New England) since August and have been on one trip with the group, a long weekend to Cape Cod. Nice bunch, just like all the other Mac owners I've run into. They tend to concentrate on the local (for us) New England area: Boston, Cape Cod, Maine, Long Island Sound, with annual extended outings to Lakes Champiain and Winnepesaukee. That's OK, too; whether I join this years' Conch Cruiser fleet or not, I'll definitely be going out with them a time or two as well.
For those as locationally challenged as I, Tobermory and Manatoulin, are in Ontario, Canada. Mapquest does just fine if you give it the right province (ON). Tobermory's on the eastern side of Lake Huron, 700-some miles and 10 trailer hours for me, so this one's a possibility.
Obviously this is a completely different trip than the one planned by the Midwest Mac group. I'll be keepping an eye on the planning, dates, etc and decide later whether I will try this one or stick with the "local" group, NE-TS.