in Chianti: Castellina

Castellina: The Wine Road Continues

Introduction (Click Here If You Didn’t Read in Chianti: Introduction)

Continuing down the SR 222, we reach the comune (municipality) of Castellina in Chianti. The origins of Castellina go back to the 7th century B.C. Its Etruscan origins are evident in the tombs just outside of town and the necropolis about 2 miles south, just off the same road.

House in Castellina

House in Castellina

The large imposing castle in the center of Castellina is a highly fortified 15th Century rocca (fortress), built to defend its strategic location between Siena and Florence. Piazza del Comune is the main square, and the town has about 2,800 inhabitants.  Castellina is a good place to shop for wine, olive oil, pottery, linens, and other traditional Tuscan products. Many quality, well respected Chianti and Super Tuscan wines are produced here including those from Costellare in Castellina, Lilliano, and Castello di Fonterutoli.  

What to See:

  • Via delle Volte – This is the enclosed and partially underground walkway on the eastern side of the village, near the main square. Interesting for its historical value, and the fact that it’s nice and cool in the Summer.

  • Etruscan Tombs – An easy walk from town. You turn on the lights when you get there and look around. The tour is free.

  • L’Antica Delizia It’s one of the best gelaterias in Chianti, if not in Tuscany. Everything is fresh and seasonal. Chiara and Simone, and there 3 children, will be happy to help you. (You’ll know you’re there by the lines out the door.)

  • Market Day – Virtually every decent size town has a market day: Booths, tents, stands, and trucks. Fresh produce, meats & cheeses. Clothing, Shoes. Flowers. Housewares. You name it. It’s where the locals have shopped for hundreds of years. Every Saturday morning.

  • Monteriggioni – This nearby town is the only preserved, completely walled-in town in Italy. Besides its architectural significance, the village has significant cultural value: In the Divine Comedy, Dante used the turrets of Monteriggioni to evoke the sight of the ring of giants encircling the Infernal abyss.



    The roughly circular walls were built between 1213 and 1219. There are 14 equidistant towers on square bases and two gates. One gate, the Porta Fiorentina, opens toward Florence to the north, and the other, the Porta Romana, faces Rome to the south. The main street within the walls connects the two gates in a roughly straight line. The Piazza Roma is the plaza between the gates.

    There are shops and trattorias in the square, along with a gelateria. The town is small enough, and unique enough, to keep everyone occupied and interested. There are some good places here to eat, and are described below.

Wine Tours/Tastings:

  • Castellare di Castellina –  If you head west on the SP130, you’ll soon come to Castellare di Castellina on your right. This is a very high quality estate, making a wonderful Chianti Classicos and Riservas. Tours are informal and need to be pre-arranged. Contact them directly:
    Web Form  |  Email:  |  Tel: +39 0577.742903

  • Rocca delle MacìeThe Girls at Rocca delle Macie – Just down the road apiece from Castellare di Castellina is Rocca delle Macìe. It’s a big winery with a fairly broad range of mass market to high end Chianti and Super Tuscan wines. Tours are informal and need to be pre-arranged. (That’s Nicole & Olivia at the winery.)

    Contact them directly:
    Email:  |  Tel: +39 0577 732236

  • Castello di Fonterutoli – Fonterutoli is an ancient hamlet a few miles south of Castellina on the SR222. (See the photo at the top of this post.) The wines – and olive oils – are nothing short of spectacular. The estate has been owned by the Mazzei family since 1435, and has passed down through 24 generations. Marchesi Mazzei is the most awarded producer of Chianti Classico. Book tours here.

Where to Eat:

  • Noah-Picking-OlivesOsteria di Fonterutoli – After taking the tour or stopping off at the enoteca for a tasting or purchase, pop across the street for one of the best (and least talked about) meals in Tuscany. The osteria offers a traditional Tuscan dining experience using only the freshest, local ingredients. The menu changes every few weeks to reflect this seasonality and excellence in quality. (That’s Noah picking olives by the parking lot.) Open every day for lunch and dinner in season.
    Email:  Tel: +39 0577 741385

    Note: The last time we ate here was 2013. We’ve since learned that there have been changes in the kitchen which have created some less-than-stellar meals. (Our friend Simon Zimbler, proprietor of Podere Patrignone, one of the top agriturismos in the Castellina area, confirms this assessment. His choice is their evening BBQ.)

  • Antico Ristorante Pestello – This restaurant is on the same road as the gelateria, but much closer to the town of Poggibonsi. While we’ve always meant to eat there, we never got to it, so maybe you can do it for us. Handmade pasta, earthy soups, and apparently unbelievable wood fire-grilled steak. Very cozy and authentic with a great wine selection. (Simon recommends their artichokes, cinghiale stew, and bistecca alla Fiorentina.) Open every day for lunch and dinner.
    Email:  |  Tel: +39 0577 740671

  • DSCF5136-Classic Porchetta Sandwich

    Porchetta Sandwich

    Bar Dell’Orso – I don’t know how we missed this place during the first two trips and two weeks we’ve spent literally livng just outside of Monteriggioni. It’s famous for its cured meats and cheeses  – especially the porchetta (pork) sandwich you see in the photo. Ask for one. The staff will slice the meat off the whole cinghiale (wild boar) that’s lying on the table right in front of you. Squisito with a beer.

    They serve all day, including pastries and snacks in the morning. There’s also live music at night. A great stopping point after seeing the town or spending a few hours at the local wineries. (See above.)

Ciao! Ciao!

Masthead photo:
Morning in Fonterutoli  (Bob)

View All Chianti Posts:
Intro  |  Greve  |  Panzano  |  Castellina  |  Radda  |  Gaiole

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Intro  |  Central Florence  |  Oltrarno  |  Santa Croce

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Como  |  Garda  |  Orta

View Other Italy Posts:
The Maremma   |   Cinque Terre  |  Bologna

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