So here's the hypothetical:

Suppose you're to drive a classic car cross country for a friend. It's a well-preserved driver and very presentable, but not super expensive (otherwise he would be shipping it.) You'll have the car a few days at your place before making the trip. And the trip also is likely to take a few days. Whether you have a companion(s) for the road trip is your choice. He'll be footing the bill for hotels, meals, and airfare back home.

In order of preference, what would be your Top 10 list of older classics (like anything before 1988) to make the journey with?

For me, I think I'd want a 1969 Alfa Romeo GTV on the list