A lot of Loopers with sailboats take the mast off for the journey - most waterways you motor as you don't have the space to tack. A sailboat is also more fuel efficient than a trawler on motor - slower, yes, but more fuel efficient.
A trawler would be epic don't get me wrong, but I love sailing - and it opens up ocean trips without the same kind of fuel worries - and you get redundant propulsion should things go wrong (and they always do).
Yeah, a lot of the ICW I saw was 100-150 yards across. And wooded right up to the shore.
But not trying to sail when you can just means you're staring down the waterway doing nothing.