All the great lakes in Canada are linked, so are many of the other lakes. I personally haven't been on any of the water ways, but I've seen a lot passing through when I've been up to Rice Lake (which is on the Trent-Severn line). Here's the Ontario-Quebec map http://www.canadiancanalsociety.org/maps/map-overview-ont-qu...
I believe you're lucky for boating if you're in the Ontario-Quebec region, I'm unsure about the US. I'm sure there's good connectivity around the boarders for Ontario and Quebec, however I have read that a lot of canals in the US were abandoned because of rail. I think Canada kept most of its canals in service, probably because it was cheaper than building rail, because in some areas you'd never get a straight line of track without a billion bridges.
If you wanted to see all of Canada by boat, I'd probably suggest getting one you can haul by trailer because there's apparently a lot to see by boat on the west coast, lots of little islands and such. However, I seriously doubt there's any way to get past the prairies (you'd probably have to ask someone who lives in those areas). Also, you'd either have to get far south every year, or your boat needs to be pulled from the water, so there's probably not as big of an option of living on your boat here unless you spent a few months in the US riding it out.
I believe you're lucky for boating if you're in the Ontario-Quebec region, I'm unsure about the US. I'm sure there's good connectivity around the boarders for Ontario and Quebec, however I have read that a lot of canals in the US were abandoned because of rail. I think Canada kept most of its canals in service, probably because it was cheaper than building rail, because in some areas you'd never get a straight line of track without a billion bridges.
If you wanted to see all of Canada by boat, I'd probably suggest getting one you can haul by trailer because there's apparently a lot to see by boat on the west coast, lots of little islands and such. However, I seriously doubt there's any way to get past the prairies (you'd probably have to ask someone who lives in those areas). Also, you'd either have to get far south every year, or your boat needs to be pulled from the water, so there's probably not as big of an option of living on your boat here unless you spent a few months in the US riding it out.