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
San Gimignano
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
Castello di Meleto
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.
To Cortona
We were dropped off in Cortona (Cortona is our favorite Tuscan town).
Organized Tours of the region
From Florence, you can take this Full-Day tour . You’ll see San Gimignano, Siena (which I wrote about here), and go to a wine estate in Chianti for wine and lunch. Recommended.
From Siena, you can take this Full-Day tour. It will take you to San Gimignano as well as to the beautiful walled town of Volterra.
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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Tanks so much for sharing. This town looks like such a cool place. I’m definitely gonna try to visit Tuscany before too long.
Tuscany is fantastic, especially if you love wine! 🙂
I have been twice to the Chianti region, both times we took a tour in Florence to Siena and San Gimignano, you can take it with guide or without which is cheaper, it all depends on your budget. both towns are beautiful and full of history, I remember the first time when approaching San Gimignano, the towers from the distance looked like skyscrapers. We haven’t done the wine tasting but we are planning to come back next year with a couple of friends and maybe we will do it. Excellent pictures and very useful tips. Thank you
Thanks for the comment Carlos! You’re right they look like skyscrapers, must have been amazing in the days when all the towers existed.
Italy is great, we look forward to coming back to this region as well.
The biggest tip for San Gimignano is to go in the morning before the hoards of tourists arrive on the tour buses. That’s the cue to get the heck out of dodge!
Very true! Thanks Jennifer.
It’s all about the smaller towns in Italy, just as you found yourselves!
Though we’re in Alberobello right now and it’s really quite lovely, it’s the smaller towns around here that are full of the most character and make for great people watching.
In my world San Gimignano is famous for vernaccia. And that’s what will lead me there one day. That, and reminders like yours. Some really nice shots here of what I’m sure is a fabulous corner of the planet.
Vernaccia: http://en.wikipedia.org/wiki/Vernaccia. I had never heard of it (I’m more a drinker of red). But will keep in mind for the next time we’re in Tuscany. Thanks for the tip Bob!
I love the first pic that you put from the Castello di Meleto. Really great post and nice pics.
Thanks for the comment Laura, happy you liked the photo!