13 Best Sights in Chianti, Tuscany

Tours here take you down to the cellars, through the gardens, and into the woods in search of wild boar (though why you'd want to meet a wild boar is anyone's guess). You can also have a delicious crostino on a terrace with latticed grape leaves forming a beautiful bower above; the view from the terrace stretches for miles. Lunch and dinner are also available, and all the food pairs beautifully with their wines—which they've been making since 1170.

The dining hall of the towering 11th-century Abbey of Passignano houses a stunningly massive, 21-foot-wide Last Supper (1476) by Domenico and Davide Ghirlandaio, and the monastery's church has a 13th-century sculpture of St. Michael slaying the dragon.

Seven different wine tours are on offer here, including a few that involve some very good food. In the capable hands of the Mazzei family since the 11th century, this gorgeous estate is a perfect place to taste some very fine wines, which pair well with items on the Tuscan menu in the osteria.

It's a pretty drive up winding roads to this 13th-century fortress. Attached is an 18th-century villa; a wineshop serves tastes of the locally produced wine as well as honeys and jams. It's worth visiting the castle, which is possible by guided-tour only (reservations required), to get a sense of how 18th-century aristocrats lived; the tour also includes a visit to the cellar and to the gardens. If that doesn't interest you, proceed directly to the enoteca for a tasting. Apartments clustered near the castle are available for rent.

At this small enoteca on Piazza della Cisterna, you can sample and purchase the fine wines, olive oil, and flavored vinegars made by Castello di Volpaia. Booked in advance, tours in English of the winery and olive press are also available.

The tiny village of Lamole contains this Romanesque church, which was greatly modified in 1860; the only remnant of its earlier incarnation can be found in its simple facade. Inside is a 14th-century altarpiece, as well as a curious side chapel on the right that is decorated with rather garish 20th-century religious works. From Greve in Chianti, drive south on SR222 for about 1 km (½ mile); take a left and follow signs for Lamole. It's about 10 km (6 miles) southeast of Greve.

At this family-run and -operated establishment, you can do a simple wine tasting, or taste while eating lunch or dinner at the rather fine restaurant. It's also possible to stay on the estate in restored farmhouses.

Built in the 1840s on a Greek-cross plan, this neoclassical church contains a Madonna and Child with angels by an anonymous 15th-century master. Also inside is the Holy Family with St. Catherine of Siena, attributed to Arcangelo Salimbeni (1530/40–79).

The oldest and most interesting of the hilltop medieval villages that surround Castelnuovo Berardenga retains its early 1400s layout, with arched passageways, gates topped with coats of arms, narrow squares, and steep streets. You can walk through the entire village in 20 minutes, but in those 20 minutes you may feel as if you have stepped back in time some 600 years.

Situated next to the castle in the upper part of town, this church was completely rebuilt in the 19th century. In the small chapel to the right of the nave is an Annunciation attributed to Michele di Ridolfo del Ghirlandaio (1503–77).

Dating from the 10th century, this walled town is oval in shape and has a tall watchtower guarding the entrance gate. A walk along the unspoiled streets gives you a glimpse of life in a Tuscan hill town as it once was, and the views of the undulating countryside from the occasional opening in the walls are simply spectacular.

Peek at the gardens of Villa Chigi, a 19th-century villa built on the site of a 14th-century castle (actually the "new castle" from which Castelnuovo got its name). The villa is closed to the public, but its manicured gardens are open on Sunday and holidays.

This tiny town, with a population of roughly 40, is perched on a hill 10 km (6 miles) north of Radda. During the wars between Florence and Siena, it served as a key castle and military outpost, but lost its importance when the Florentines defeated Siena in 1555. Approximately three-quarters of the town is now given over to the production of wine and olive oil.