23 Best Sights in Chianti, Siena, and Central Tuscany, 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.

Caterina Benincasa, born here in 1347, had divine visions and received the stigmata, but she is most famous for her words and her argumentative skills. Her letters—many of which are preserved in the Biblioteca Comunale—were dictated because she did not know how to write. She is credited with convincing Pope Gregory XI (1329–78) to return the papacy to Rome after 70 years in Avignon and French domination, ending the Western Schism. Caterina died in Rome in 1380 and was canonized in 1461.

In subsequent centuries, the rooms of the house, including her cell and the kitchen, were converted into a series of chapels and oratories and decorated by noteworthy artists with scenes from Caterina's life. In 1939, she was made a patron saint of Italy, along with St. Francis of Assisi. In 1970, she was elevated to Doctor of the Church, the highest possible honor in Christendom. She has been named a patron saint of Europe but, strangely enough, never of her hometown.

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.

Walk along Via San Lino, through Porta San Francesco, and out Borgo Santo Stefano into Le Balze—a haunting, undulating landscape of yellow earth drawn into crags and gullies that's thought to be the result of rainwater wearing down the soil substructure. This area was originally part of the Etruscan town of Velathri, as evidenced by walls that extend 1 km (½ mile) toward the old Porta Menseri. Toward the end of the road, on the right, is the church of San Giusto (with terra-cotta statues of the town's patron saints) built to replace an earlier church under which the earth had eroded. The bus for Borgo San Giusto, leaving from Piazza Martiri, goes through Le Balze (about 10 runs per day).

Even with all the decoration in the Collegiata, the fine collection of religious articles in the church museum, across the pretty courtyard, is still worth a look. The highlight is a Madonna and Child by Bartolo di Fredi. Other pieces include several busts, wooden statues of Christ, the Virgin Mary, and the angel Gabriel, and several illuminated songbooks.

The religious-art collection housed in the Bishop's Palace was collected from local churches and includes an unusual reliquary by Antonio Pollaiolo with the head of St. Octavian in silver resting on four golden lions. There's also a fine terra-cotta bust of St. Linus by Andrea della Robbia (1435–1525/28). Two paintings are noteworthy: Rosso Fiorentino's (1495–1540) Madonna di Villamagna and Daniele da Volterra's (1509–66) Madonna di Ulignano, named for the village churches in which they were originally placed.

Siena's botanical garden is a great place to relax and enjoy views onto the countryside below. Guided tours in English are available by reservation.

Tuscany's first town hall, built between 1208 and 1254, has a no-nonsense facade, fortress-like crenellations, and a five-sided tower. It later served as a model for other town halls throughout the region, including Florence's Palazzo Vecchio. The medallions that adorn the facade were added after the Florentines conquered Volterra. The town leaders still meet on the first floor in the Sala del Consiglio, which is open to the public and has a mid-14th-century fresco of the Annunciation.

Across the piazza from the Collegiata is the "old" town hall built in 1239. Its tower was erected by the municipality in 1255 to settle the raging "my-tower-is-bigger-than-your-tower" contest—as you can see, a solution that just didn't last long. The palace is closed to visitors.

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.

If you want to see more of that quintessential Tuscan landscape, walk up to the Rocca di Montestaffoli, which sits at the highest point in San Gimignano. Built after the Florentine conquest to keep an eye on the town, and dismantled a few centuries later, it's now a public garden.

Look inside the church for the celebrated early-15th-century frescoes of the Legend of the True Cross by a local artist. It traces the history of the wood used to make the cross upon which Christ was crucified. From Piazza San Giovanni, take Via Franceschini (which becomes Via San Lino) to the church.

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).

Down a small street around the corner from Il Campo, this synagogue is worth a visit simply to view the two sobering plaques that adorn its facade. One commemorates June 28, 1799, when 13 Jews were taken from their homes by a fanatic mob and burned in the square. The other memorializes the Sienese Jews who were deported during World War II. Visits are permitted every half hour, and guided tours in English are available by prior arrangement.

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.