A trip through the hilltowns of Tuscany
The hilltowns of Tuscany – some of the most beautiful towns (and geography) you’ll see in all of Italy. We started this day in wonderful Siena and ended the day in Cortona, seeing lots of little Tuscan hilltowns in between.
Related: Why Siena is Incredible
Leaving Siena, our first stop was the beautiful town of San Gimignano. The town is famous for the towers built by its wealthiest citizens as symbols of their power. There used to be 72 towers in the town, only 14 are still standing which is nevertheless amazing considering the small size of the place. In the Middle ages San Gimignano was a stop for pilgrims on the Via Francigena, the ancient road that linked France to Rome and the Vatican.
Below: San Gimignano’s skyline.
One of the many things I love about Italy are all the towers, every town seems to have one. The most famous one in San Gimignano is the Torre Grossa. The tower is actually kind of deceiving from the bottom. Looking up from the piazza, it doesn’t look like much. But climb up and you’ll find the views extraordinary. It is a highlight of San Gimignano and climbing it is a must.
Below far right: The tower from the piazza. Doesn’t look very high, right?
Below: incredible Tuscan views from the top
The Towns of Chianti
After San Gimignano, we drove into the Chianti hills, the heart of the Chianti region. We stopped in a few of the small towns; Castellina in Chianti and Radda in Chianti, medieval little towns with more towers and old buildings. Only wines from this area can have the Chianti Classico label (the black rooster). It is a beautiful area that is popular with cyclists, wine enthusiasts, as well as those wishing to visit the region’s castles.
Below: our guide showing off the black rooster label
Driving up higher into the hills, we toured the Casamonte farm for some wine tasting. It is a beautiful estate where they not only produce their own Chianti Classico wines, but also Olive Oil and pork (from Sinta Senese pigs, rare pigs that they breed). I fully recommend coming here for a tour – my only caution is that you don’t have wine shipped unless you have experience/knowledge of the import laws at home. I fell in love with Casamonte’s Super Tuscan wines (Sangiovese grapes mixed with Cabernet Sauvignon and Merlot in varying degrees) and made the mistake of have a case shipped home. I would end up having to pay double to price at home in import taxes. Never again.
Below: Casamonte farmhouse
After Casamonte, we visited Castello di Meleto (click on that link if you want to stay there) a large castle close to the town of Gaiole in Chianti. Besides having it’s own winery, the castle provides accommodation. I’d love to come back and stay here. We were given a tour, seeing underground tunnels and a small theatre dating from the 18th century (photos below). The castle is another great stop in the region.
We were dropped off in Cortona (Cortona is our favorite Tuscan town).
Organized Tours of the region
This is a stunning region.
Related: 3 Days in Florence
Have you been to this area? Do you have a favorite town?
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