An itinerary through the main towns of Chianti

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Discover Chianti and its beautiful towns

Only a few regions can offer such a beautiful and rich panorama as Chianti: green hills sketched by miles and miles of vineyards and olive groves, ancient walled villages, panoramic curvy roads. Chianti Classico spreads from Florence to Siena and includes the municipalities of Greve, Panzano, Radda, Gaiole and Castellina.

Greve in Chianti

Our trip starts in Greve in Chianti, considered by many as the gate into Chianti. This lively town is famous for its particularly shaped piazza or square that has been market place for the castles and walled villages in the surroundings since the Middle Ages. The square has a triangular shape and large porticos along three sides that protect from sun and rain while shopping. In the center stands the bronze staue of Giovanni da Verrazzano, explorer that discovered the Bay of New York. At the top of the square stands the Church of S. Croce, originally a medieval church remodeled according to Renaissance Revival architectural style, displays a few precious works of sacred art including the triptych depicting Madonna and Saints by Bicci di Lorenzo.

Greve presents many different places where you can taste Chianti wine and enjoy local food. The porticos host many workshops, wine bars and restaurants. One that requires mentions is the Antica Macelleria Falorni, a historical butcher shop that sells only typical products produced in Chianti. Just a few steps away stands the Wine Museum which we recommend visiting.

Panzano in Chianti

Panzano is the most populous town in Chianti and sits just a few kilometers south of Greve. Since the 12th century, Panzano played an important defensive role for Florence and its county. The Castle of Panzano was a fundamental bulwark for defending the Florentine Republic during the battles between Florence and Siena. The castle's structure can be still recognized within the older section of town including the Church of S. Maria which dates back from 1200 even if it was completely rebuilt in the 1800s in Neoclassical style.

It is really nice to wander through the old town, soaking the atmosphere of times gone by and sitting in the main square drinking a glass of Chianti wine. There are several wine bars and restaurants in Panzano that offer wine tasting while a popular place to visit is the Antica Macelleria Cecchini, a butcher shop famous for its Florentine steak where the owner recites passages from Dante's Divine Comedy while serving customers.

Not far stands the Pieve di San Leolino, an ancient rural church dating back to 982. In spite of the Renaissance exterior characterised by the elegant "pietra serena" stone and portico, the church remains an exquisite example of a Romanesque basilica with three naves. Inside are displayed some precious works of art by local masters.

Castellina in Chianti

Moving towards Siena you'll reach Castellina in Chianti which dates back to the Etruscans, as attested by the Etruscan tombs of Montecalvario. Its great position in the middle of the Chianti region made Castellina a strategical headquarter between Florence and Siena. Confirming this glorious past, the massive Rocca (castle) stands proudly over the city and the impressive Via delle Volte, an underground tunnel around the city, offers breathtaking panoramic views. Walking through the small town you will notice many historical buildings that belonged to Florentine and Senese aristocracy. The Church of S. Salvatore merits a visit; rebuilt after the Second World War, the church displays a beautiful late 14th century fresco by a Tuscan master. We also recommend the Archeological Museum of Chianti Senese where many archeological findings from the Chianti region, and particularly Etruscan findings from Montecalvario, are displayed.

In Castellina you can taste wines in one of its various wine bars and the great, unforgettable taste of its many fresh and aged salami and cold cuts which have become an age-old art in Chianti and Tuscany.

Radda in Chianti

Leaving the Chiantigiana road and taking the SR429 you reach Radda in Chianti that even today preserves its original medieval look. The ancient walls still defend the center, today filled with maze-like streets. The Palazzo del Podestà overlooks the main square together with the Romanesque Church of S. Niccolò. The Palazzo was the headquarters of the League of Chianti for over four centuries, as confirmed by the many coats of arms on its facade. Just outside the center stands the ancient Franciscan Cloister of S. Maria in Prato.

It is really nice to get lost in Radda wandering around its medieval streets, drinking a glass of wine while looking at the spectacular panorama of the vineyard covered hills that surround the town.

Near Radda stands the Castle of Volpaia, an ancient walled town which we recommend visiting. The castle in sandstone has a distinctive dark color that makes it different from other castles in Chianti. In spite of the marks of the numerous wars between Florence and Siena, the main structure can easily be recognised in the massive tower and one of the minor towers. We also recommend stopping at the Commenda of S. Eufrosino, a 14th century church transformed into a wine bar. Today the Castle of Volpaia is a small tourist town where you can experience the ancient culture of wine.

Gaiole in Chianti

Not far from the Radda and the Castle of Volpaia stands Gaiole in Chianti, another town dating back to the Middle Ages. Gaiole was an important market place for the castles in the surroundings because of its position between Chianti and the Valdarno (Valley of the Arno river). Gaiole is still an important point of interest in this area. As a matter of fact, you can find many farmhouses, wine shops and wineries perfect for Chianti wine tasting and as well as lodging for your holidays.

There are many castles and fortified towns around Gaiole that deserve a visit. For example, the Castle of Vertine, the Castle of Meleto and the Pieve of Spaltenna can be visited, either through staying there during your holiday or through a special wine tasting and winery tour.

If you want more information and suggestions about wine tasting in Chianti, you can read our article "Wine Tasting in Chianti".

View our photo gallery of the Chiant Area View our beautiful pics of the Chianti Wine Region! »

~Discover Tuscany Team

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