Discovering The Hidden Towns of the Tuscany Countryside

You can catch a train to see some of its major towns, but if you want to truly experience the Tuscan countryside and relish its landscape and quaint villages, your best bet is to drive.

Since we did not have a car, we booked a day tour with Alessandro Cammilli Private Tours. Alessandro is a local guide who has grown up in Florence and knows Tuscany like the back of his hand. Our route took us to what is known as La Chiantigiana, the main north-south road through the Chianti Classico, stretching from Florence until Siena.

Towns, Wineries and a Tranquil Route

The region's Chianti wine is world renowned for its quality and produced throughout Tuscany. As we went from a small town to another, our road meandered through extensive wineries which blanketed the region’s hilly landscape.

If you are interested in experiencing the tranquil side of Italy and want to take a break from its big cities, I recommend taking at least a day from your busy schedule and tour the Tuscany countryside.

San Gimignano

Sitting along a former pilgrimage route from northern Europe to Rome, San Giminiano was once a very wealthy town. Its striking skyline used to be dominated by 72 towers built by noble families in the 12th and 13th centuries as symbols of their wealth and power. Although only 14 of these towers have survived, San Giminiano still retains its feudal atmosphere and its stunning medieval architecture.


Built in 1203 and enveloped by high towers to guard the northern border of Siena’s territory, Monteriggioni is one of the most significant walled castles in the region. The medieval town is incredibly preserved, as if time had stopped on the hilltop from which it overlooks the countryside.


Located atop a hill, the city of Castellina in Chianti sits along the Chiantigiana road connecting Florence to Siena. There are not many things to see and do around town; however, it is a great stop to take a rest from driving while exploring its historical main street.


Once rivaling the capital Florence during its peak, Siena is considered the loveliest medieval city in Tuscany. The heart of town is its semi-circular Piazza del Campo that breaks from the cluster and maze-like streets that surround it. If you don’t mind large crowds, the city’s iconic horse race Palio di Siena is held in this square twice in the summer.


Considered the entrance to the Chianti region along the Chiantigiana road, Greve in Chianti is a great stop to enjoy some artisanal products. Numerous local shops line its open square where you can buy products such as cheese and meat. One of its more famous is Antica Macelleria Falorni, a historical butcher shop.

Fattoria Montagliari

This family run winery has been producing traditional Chianti since 1720, alongside its olive oils and 20 to 28 year old balsamic vinegars. Located amongst the rolling hills of the Tuscan countryside, this small farm welcomes visitors to their farm store and restaurant.


The Warp Up: We left Florence in the morning and came back late afternoon. It was a full day’s drive, but the best experience we had during our two weeks in Italy. We learned more about the Tuscan region than we had originally expected and left it with a much better appreciation of the Italian culture and everyday life.

The Castle and Hotel: Castello Vicchiomaggio is a historical hotel and working wine estate located atop Tuscan hills near Greve in Chianti. We did not stay in this hotel since we were based in Florence, but it was highly regarded by our guide.

The Restaurant and Butcher: Located in the hilltop town of Panzano in Chianti, Antica Macelleria Cecchini is a butcher shop better known for its famous butcher Dario Cecchini. Being an excellent cook and a promoter of traditional food, Dario opened a restaurant called Solo Ciccia (only meat). This communal restaurant may require a reservation due to its limited seating and hours. 

- Want to see the full trip and plan your next? Check out our Italy Two Week Itinerary!