Autumn in the hills of Umbria and Tuscany a very different Italy emerges: languid and relaxed, as Italians sit back and chat amongst themselves, or with you, over a dish of pasta, or a tiny espresso.

How does a young man get his peers’ attention? Here’s how I did it in 1979—I saved up my money from a part-time grocery store job and bought a car that others would envy: a 1969 Oldsmobile Cutlass 442 convertible with a Hurst shifter. And it worked: mine was the only “drop top” among my friends,...