We met a Swiss boat in Mexico a few years ago. They’d sailed from Europe to Caribbean, then in US north then west thru Great Lakes to Chicago. Shipped the boat from there to Seattle, then down west coast. We met them in La Paz, and they raved about what a great trip it had been.
Not a bad plan. Georgian Bay is wonderful as well as the Pacific Northwest. The problem in the Great Lakes as everyone knows is the short sailing season, three months.