My brother always wanted to take his sailboat down the Tenn-Tom to the Gulf of Mexico, sail around the tip of Florida, and back up the east coast to the St. Lawrence. Then up the St. Lawrence to the Great Lakes, on to Chicago, get back into the inland waterways, back to the Mississippi River, to the Tennessee, and back home to the Tenn-Tom. Unfortunately, that "widow maker heart attack" got him before he had the chance.

In my mission trips to Fiji I've seen boats from all over the world in the harbors at Suva and at SavuSavu. Doing that sort of thing is something interesting to contemplate.