You're not crazy, it'll be a fabulous trip. I run the Gentleman Drivers Club and we do various drives in the UK and Europe each year. You should ship your car to the UK, take in some of the Welsh roads then go over to France on the tunnel. From Reims down to the Route Napoleon to Monaco. Col di Turini then up through the Italian lakes to Stelvio Pass, Furka Pass, Gottard, etc. - best roads in the world. Portofino is stunning, as is much of the Mille Miglia route - a few days baiting Ferrari test drivers out of Maranello up in the hills through Stella never gets old. The drivers in Italy are particularly challenging, but as long as you assume some may make the worst decisions, then you'll be fine. It's the minority that drive without care.
This book is in German, but it shows some of the best routes and great photography.
Escapes -- Traumrouten der Alpen - YouTube
There's some great roads through the Black Forest towards Suttgart too - and the Museum is naturally fabulous. Try to time it to coincide with either Goodwood Revival or Le Mans Classic on the way back to England and you'll have a trip that you'll never forget. I've done this sort of trip maybe a dozen times, and I love every minute of it.
If I can be of any assistance, let me know. If you make it to the UK, I'll happily meet up with my 1966 911 SWB and some mates to show you some great UK roads...