The Tuscan region of Chianti is home to several small, but significant villages. And many of these small towns have much to see. The nearby town of Greve holds the region’s largest wine fair every September. Today it is a wine-lover’s paradise and is a must-stop location to sample the local wines. The best ones are located in the center of the town near the Piazza Matteotti. Here you can also see the statue of Giovanni de Verrazzano, a native of the village and the European who discovered the New York harbor.

To the East, along a very twisting but beautiful road, is the village of Radda in Chianti, which is also quite an old town with its own lengthy and unique history. The village retains its tight medieval streets and architecture that predates that Renaissance. The focal point of the village is the Piazza Ferrucci, the town hall that features lavish frescoed decorations, various ancient crests and other reminders of the importance the town played in the struggles between the powers in Florence and Siena. Across from the square is the town’s Gothic church, which seemingly stands guard over the piazza.

From the small towns of Greve and Radda, you can head to San Casciano Val di Pesa, which is the largest of the towns in Chianti. Here you can take in the city’s old 14 th century defensive walls, and several late Middle Ages and early Renaissance buildings including the Church of Santa Maria del Prato, which today houses numerous works by Fra Bartolomeo and Simone Martini among others.

South of Castellina, don't miss the opportunity to visit Monteriggione a tiny old hilltop town still encircled by its protective wall.  Although Monteriggione is now filled with tourist-y restaurants and shops, it still makes for an interesting visit.  Surprisingly, there is even a 4-star hotel in Monteriggione.