Begin your full-day private tour of Tuscany's countryside with pick-up at your hotel or other accommodation in central Siena, and enjoy the scenery as you head out of town with your guide.
Stop first at the San Galgano Abbey, an impressive Gothic structure that – somewhat surprisingly – does not have a roof. Walk a short distance from the abbey to the Hermitage of Montesiepi, where you can see what many say is the original inspiration for the story of the 'sword in the stone.'
Head next for the town of Murlo, which dates to the Etruscan era. The next stop is the hilltop town of Montalcino, famous for its wine-producing history. Stroll the charming, cobblestone streets. Visit the town's fortress, which was built in the mid-14th century. The fortress walls offer spectacular views overlooking the town and surrounding area.
Stop for lunch at a restaurant in old town, where you'll also sample some of the estate's wines.
Continue to Sant'Antimo Abbey for a visit to this 11th-century structure, where you might just hear Gregorian chants as you explore the grounds and take in the scenery.
The final stop of your tour is an organic wine estate in Brunello en route back toward Siena. There, you'll get to visit the wine cellars to find out how the famous local wines are made. Sample some Rosso and Brunello di Montalcino before heading back to Siena and getting dropped off at your original departure point.