I made a 13 days tour with a team of 9 Morgan in 2019.
Toulouse to Toulon by road, ferry from Toulon to Trapani.
Trapani, Palermo, Reggio di Calabria, Cosenza, Palinuro, Napoli, Rome, La Spezia, Toulouse.
No problem with the Morgan. I guess this is better to take the Morgan than the Mercedes in term of security (theft), but you have to find hotel with a private garage in Sicily particularly in Palermo and the great towns.
In some small towns like Cosenza, Palinuro we were on public parking in front of the hotel without problem.
In the South some roads are not good, better in the middle and the North, but you can manage.
For your trip you can take a ferry to Bilbao in Spain and after join (2 days) Toulon by road going along the Pyrenees and the Mediterranean sea.
