Val d’Orcia from Florence

If the Tuscany in your head is a white road winding through cypress trees to a hilltop town, you are picturing the Val d’Orcia. It lies south of Siena, about two hours from Florence, and it is worth a full day of its own.

The towns

Montalcino is the home of Brunello, one of Italy’s most prized reds, and its cellars pour it by the glass. Pienza was rebuilt in the 1460s by a Renaissance pope as his ideal town; today it is famous for pecorino cheese and a promenade along the walls with the whole valley below. Montepulciano climbs a long, steep main street lined with palaces and old wine cellars, the home of Vino Nobile. Between them sit the scenes from the posters: the little chapel of the Madonna di Vitaleta, lines of cypresses on bare hills, and the fields near Pienza used in the film Gladiator (private land, so you see them from the road).

The group tour

The Val d’Orcia day trip (4.7 from over 1,500 reviews, from about $107) runs about 11.5 hours from Florence by coach with Wi-Fi. It includes a Brunello tasting in a Montalcino cellar, free time in Pienza, a stop at the Vitaleta chapel, and a Vino Nobile tasting with cheese in Montepulciano. Lunch is at your own expense. Reviewers love the scenery and the tastings; the recurring comment is that three towns in one day feels brisk, and guides may repeat commentary in several languages.

Private or self-drive

With a car, the Val d’Orcia is the easiest part of Tuscany to explore alone: quiet roads, parking outside each town’s walls, and the famous viewpoints right by the road. Stay a night in Pienza or Montepulciano and you get the sunset without the drive back. A private tour with driver costs several times the group fare, but it means nobody has to skip the tasting. If you only have one day in Tuscany, though, the Siena and San Gimignano day is closer and easier.