The Wall Street Journal has a fun article on loopers. Loopers are people with reasonable sized watercraft who circle the eastern United States by boat.
They sail up the Intercoastal Waterway from Florida to New York City, up the Hudson River to the Erie Canal, across to Lake Ontario, down Lake Erie, up past Detroit to Lake Huron, around the top of lower peninsula Michigan past Mackinac Island , down Lake Michigan to Chicago. There they take the Calumet Canal to the Des Plaines River, which connects with the Illinois River, which merges with the Mississippi River just north of St. Louis, down Old Man River past New Orleans to the Gulf. They then follow the coast east to Pensacola, Tampa, and around the tip of FL back to Miami, closing the loop.
Dang, that odyssey looks like fun. It's sort of "RVing on water," seeing the country at sea level. We've done much the same kind of trip on land in a succession of RVs, and that was a hoot. And yes, in RVs like in boats, you are never far from your toolbox, and a roll of duct tape is always handy.