• MONTEFIORALLE (Greve in Chianti)

Montefioralle, listed among the "100 Most Beautiful Medieval Villages in Italy," dates back to the 11th century and was once a key defensive stronghold. Its well-preserved stone walls and towers still offer stunning views of the Chianti region. The village is the birthplace of Giovanni da Verrazzano, the explorer who discovered New York Harbor in 1524. A plaque marks his birthplace near the village square.

The Church of Santa Maria, built in the 11th century, features Romanesque architecture and beautiful frescoes. Legend says the name "Montefioralle" comes from "Mons Floralis," meaning "Mountain of Flowers," a nod to the surrounding lush landscape.
Take about an hour to explore its narrow streets, historic buildings, and breathtaking views—an authentic taste of Tuscany’s past.

• PANZANO IN CHIANTI

Panzano is a peaceful town nestled in the heart of Chianti, where you’ll find yourself admiring the stunning blue-green valleys and fiery sunsets. It’s home to the renowned butcher Dario Cecchini, whose shop is a must-visit. The town is also dotted with wineries, making it a perfect stop for wine lovers.

Allow about 2 hours to explore its charming streets, soak in the views, and perhaps enjoy a taste of local delicacies and wines.

• RADDA IN CHIANTI

Radda-in-Chianti is a picturesque town with a historic castle, located in the heart of the Chianti Classico wine region. Known for its deep wine heritage, it was once the administrative center of the Chianti League during the Middle Ages. The town’s main square, Piazza della Repubblica, features the beautiful Palazzo del Podestà, a medieval building that still serves as a symbol of Radda’s historical importance.

The surrounding vineyards produce some of the finest wines in the Chianti Classico region, including the famous Chianti Classico DOCG. Spend about 2 hours exploring Radda’s narrow streets, visiting the wine cellars, and taking in the breathtaking views of the rolling hills and vineyards.

• CASTELLINA-IN-CHIANTI

The charming town of Castellina in Chianti offers stunning landscapes, locally crafted gelato at Gelateria di Castellina, and panoramic views from the historic Rocca di Castellina. The Rocca, a 14th-century fortress, provides a spectacular vantage point over the rolling vineyards and olive groves of Chianti. Take your time to explore the medieval streets, visit the Archaeological Museum of Chianti, and indulge in the local treats. Allow around 3 hours for a leisurely visit to fully enjoy its beauty and history.

• VOLPAIA

Volpaia is one of those hidden gems in the Chianti hills, where time seems to slow down. The village dates back to the 11th century, and you’ll feel its history as you wander through the narrow stone streets. It’s quiet, with beautiful views of the vineyards and olive groves that surround it.

If you enjoy wine, it’s worth stopping by the local winery, where they make some of the best Chianti Classico. The Chiesa di San Donato is also a lovely spot to visit. We’d recommend allowing about 2-3 hours to explore at a leisurely pace and take in the peaceful atmosphere.

• SAN GIMIGNANO

San Gimignano is famous for its impressive medieval towers, which once served as symbols of wealth and power. The town offers breathtaking views from the top of Torre Grossa, where you can see the surrounding countryside stretching out below. As you explore its charming streets, don’t miss the chance to stop for some of the best gelato you’ll find in Italy.

The town’s medieval architecture, along with the Collegiate Church of Santa Maria Assunta and its beautiful frescoes, adds to the experience. Plan for about 4-5 hours to wander at a relaxed pace, enjoying the views, history, and the lively atmosphere.