I experienced the trip going the opposite direction about 12 years ago when we bought our boat in the Chesapeake and sailed it up to Montreal. We ran out of vacation
time dealing with the closing of the sale
, etc. so we had the choice of trucking our boat north ($5,000+ were the quotes from Solomons Island to Montreal) or sailing it up on weekends and leaving the boat at marinas
during the week. The trip ended up costing us about $3600 all in including gas back and forth each weekend but both my wife and I agree it was one of the best experiences we ever had. We met so many great people and learned so much about our boat in those first 8 weekends. We saw so many great places and enjoyed one of our best trips ever to New York
(staying on a mooring
at the 79th street boat basin). If you have the time to do the trip, you will not regret it. Sure you can truck the boat and have access to it down south, but will you ever get the chance again to see that great expanse between Georgian Bay and Florida
My advice to you would be to wait until the spring, spend a few weeks cruising in Georgian Bay and the North Channel (according to the book of the same name, one of the best "places to sail before you die"), then sail her down through the Great Lakes
to Oswego and follow the Erie canal to NY, along the Jersey shore to the Delaware canal, down the Chesapeake and beyond. I would even join you for the first week or two if you'd like up in the Great Lakes
. You will see more variety and experience more amazing things than you will ever see just staying in one area.
Or you can drive the interstates. Your choice!