What is maximum mast height? There are loops in Europe like this, but you need a mast that you can take down, which means you are limited in boat size - for sailboats anyway.

19.6’,limited by a bridge outside Chicago. Several routes require a maximum 15’ height and others are 17’. https://www.greatloop.org/great-loop-information/great-loop-...

I’ve been utterly fascinated by this since I learned about it a few months ago. It seems like a very approachable but still serious adventure and achievement once done.

Sounds like a great trip (IF you like being on a boat).