TWO boats. The OP has TWO boats! Neither one of them ready for the ocean.
I still consider myself a boater at heart. Used to do at least 40 nights on the water a year & spent 18 years actually working on the water.
Many years ago for our years AC, that is After Children, we considered getting a boat, a 45' or so trawler, & doing the waterways of N America with it. It didn't take long before that idea was scuttled. Too many places that a boat cannot go & way more expensive than a RV to boot. Boats don't do mountain passes very well.
We bought the RV with the idea that after a few years we would have had enough of the road & go back to our weekend boating in Bermuda with our 32' Albin. It did not work out that way.
Should have sold the boat. 11 years & almost 200,000 miles on our truck we are still going strong. Meanwhile the boat sits in a cradle in storage on property we own.
Our 34' 5er has at least as much living space as a 40' trawler. Far more than a sailboat even longer.
Ideas of shipping your US truck around the world are not going to work. Where will you get parts & who will service it when things go wrong. For world travel you need to start with a world vehicle. Best to rent what you want where you want it. That 50' cat is not going to work on the canals of Europe but there are plenty of charters over there.