How big of a boat? I used to photograph lots of cruisers, up to 40 feet. I always thought having one would be great, moored on Lake Michigan, just an hour from the city where we had the studio. Then we thought about it. Only 4 months of weather good enough to make being on it pleasant, dock fees, storage fees, fuel costs if you actually took it out, maintaining it....well you know the picture.
Then the 08 crash ended the marine business and I was no longer tempted whenever a nice big cruiser came into the studio. Luck me😂
Many years ago, I amused myself one summer by travelling to and photographing every lock on the Trent-Severn river system, which is a major recreational boatway from Trenton, Ontario to Port Severn on Georgian Bay. At one of the locks I met a couple in a fairly large sailboat from Ann Arbor, Michigan. They had spent the summer travelling by boat, not sure of their departure point, but they made their up Lake Michigan, across Lake Huron and Georgian Bay, down the Trent-Severn to Trenton, then across Lake Ontario to the Rideau River system locks all the way to Ottawa and were on their way back home via the same route. Wouldn't 2020 be a perfect summer for that kind of voyage, gas is cheap, probably less congestion at the locks, etc.