Head out of Siena in the morning traveling toward the medieval town of San Gimignano. Along the way, stop in the tiny town of Monteriggioni, a charming village on a hill that is defined by the centuries-old walls that encircle it. Stroll around the town, taking in the views and walking along the walls, learning from your guide about the history of the place.
From there, hop back in the automobile for San Gimignano, enjoying the rustic Tuscan countryside along the way: the villa-topped hills, the vineyard-clad rolling mounds of earth and the olive groves. Once in San Gimignano, walk down the Via Francigena, a pilgrimage route from the Middle Ages that stretches from Canterbury in England all the way to Rome. The path goes right through San Gimignano. Learn from your guide about pilgrims in the Middle Ages and even today that would trek through France and Switzerland, even the Alps, to eventually get to Rome.
Take some free time to do exploring on your own. Walk the narrow cobblestoned alleyways. Stare out at the vast Tuscan landscape before your eyes. Ascend one of the 14 matchstick-like stone towers, which were once inhabited by families in the Middle Ages. Linger for a while in Piazza del Duomo and perhaps pop into the church, the Collegiata. The exterior facade may look dull but the black-and-white striped Gothic interior is a showstopper.
After some exploration, take a load off for lunch at a family-run farm just outside of town. Feast on locally made delights such as cheese and prosciutto. And don't miss anything made with the locally produced saffron in it.
Later that afternoon, take a scenic drive south to the town of Volterra. The town, known for its alabaster -- the translucent stone used for centuries to create vases, lamps and other works of art -- is an aesthetically pleasing place to spend a little while. Watch craftsmen ply their trade and spend some time strolling the streets.
After about an hour, hop back on the bus and head back to Siena.