We left behind San Gimignano—the tower city—and followed the Via Francigena to Monteriggioni—the walled city.

It was a day of ups and downs, showing off gorgeous Tuscan views from a sometimes rugged trail along with many miles of arduous and even dangerous road walking.

At one water crossing, longer and trickier than the one in the photo above, a young guy yelled out as I started, “Need some help?” Thanks to practice on the John Muir Trail, I handled the crossing on my own with no problem. I am fighting taking offense, though, when a whippersnapper assumes that my age makes me feeble.

By the end of nearly nine hours, we covered nearly 19 miles and 2,400 feet of ascent, including a final push up an achilles-testing climb to the imposing walled city.

In one day, our feet covered two of the most beautiful places in all of Italy.