Max Fletcher is also headed in your direction with similar plans(which sound terrific). It's an area of the world we could spend a lot of time exploring. Having a base to travel out of-inland, makes even more sense to have your boat there. I envy your coming adventure in the Med., John. We still miss Vermont having moved from there 15 years ago. We get back often.
We considered sailing that (EU) area of the world a few years ago. Everything from sailing there ourselves to shipping the boat(while working), and the cost comparisons. We're in a good seasonal rental market here which helps fuel these ideas.
But the logistics didn't work for us, so we flew a few times. Then as it turned out both our kids ended up studying in the EU so we've had a few opportunities to get over there in the last years and will likely be going again in the next year.
Our son is thinking of living in Italy now so it could become more of our lives. Another idea of late is to rent a 'Caravan' (camper) for a month or so to cover some ground and see more of the countries.