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Castellina in Chianti: Everything You Need to Know + Itinerary

Panoramic view from Castellina in Chianti

Tucked away in the lush Tuscan countryside, amidst rolling hills, vineyards and olive groves, lies the enchanting village of Castellina in Chianti. This picturesque destination has a very authentic, old world feel to it. It’s not overrun with tourists or souvenir-stuffed boutiques. For this reason, I find Castellina in Chianti to be one of the best day trips you can take within the Chianti region.

How to Get to Castellina in Chianti

By Car

The easiest way to get to Castellina in Chianti is by car. The town center is just a 38-minute drive from Siena or a 50-minute drive from Florence. There are several small parking lots off the main road as you enter into town. Most of these lots are free to use, but look for signage just to be sure. Since the town is on a hill, maneuvering your vehicle into and out of a small spot can be challenging. Just be careful, go slow and you’ll be fine!

By Bus

From Siena, take the 125 bus towards Lucarelli Capolinea. The ride will take about 35 minutes. If you’re using Google Maps to navigate, I would set Taverna Squarcialupi as your destination, as that will lead you to the best part of town and the perfect starting point.

From Florence, I would not recommend taking the bus, as it would involve multiple transfers and take over two hours. Instead, consider booking this half-day tour of the Chianti region. A private bus will take you through some of the best Chianti locations, including Lornano, Castellina in Chianti and Monteriggioni.

Castellina in Chianti town center

Planning Your Visit

Lunch at the Best Restaurant in Castellina in Chianti

I’d recommend arriving in Castellina in Chianti around lunchtime. Make a reservation in advance on the panoramic terrace of Ristorante Taverna Squarcialupi for some of the best lunch views of your life. The food here is stellar and the service so very friendly.

The view from Taverna Squarcialupi
The view from Taverna Squarcialupi’s back terrace.

I ordered the Chianina marinata with pecorino fondue for a starter and the carbonara del Toscanaccio for my main. Both dishes were excellent. Taverna Squarcialupi’s bread and pasta is made with wheat from their own farm, down along the hillsides. Their house wines are organic and also produced just meters away from your dinner table.

Taverna Squarcialupi

I can’t overstate how impressed we were with this Castellina in Chianti restaurant. They even have a wine cellar on-site where the wine is stored in large wooden barrels. A stroll through the cool, dim aging rooms was much-needed on a hot summer day.

Ristoranti Castellina in Chianti

What to Do in Castellina in Chianti

Rocca Comunale

Rocca Comunale

After lunch, mosey on up to the town’s medieval fortress—the Rocca Comunale. Entry is inexpensive and the fortress was nearly empty when we visited—a welcome respite from the lines and crowds of Florence. Bring your camera because the panoramic views atop the fortress make for a great photo opportunity.

Visit the Church of San Salvatore

The beautiful Chiesa di San Salvatore, or Church of Saint Salvador, is located about one minute from the town’s main fortress. This place of worship houses the body of San Fausto, the Patron Saint of Castellina in Chianti. Additionally, the church’s exterior steps offer an excellent place to stop and rest during an afternoon of exploring.

Via della Volte in Castellina in Chianti

Walk the Via delle Volte

This ancient arched passageway was once used for religious and military purposes to protect Castellina in Chianti’s borders. It is now a little piece of this town’s history you can peruse yourself. It’ll only take a few minutes to walk the length of the passageway. You might consider stopping at the delicious Ristorante Sotto le Volte for a snack along the way.

Best Wineries in Chianti

Castellina in Chianti is part of the prestigious Chianti Classico wine region, renowned worldwide for its exceptional wines. The vine-clad hills and sun-drenched fields provide the ideal terroir for the production of Sangiovese grapes, the backbone of Chianti Classico wines. No visit to Chianti would be complete without sampling a few of these delicious wines.

Querceto di Castellina

I highly recommend visiting Querceto di Castellina, a farm and vineyard just a 12-minute drive from the Castellina in Chianti town center. They offer wine tastings if you’d like a guided experience, or you’re always welcome to visit their Livia Wine & Cheese bar—no reservation required! We loved sitting on the patio for a couple hours, sipping our wines, taking in the vineyard views and playing with resident pup Elliott. This Castellina in Chianti winery truly has something for everyone.

Querceto di Castellina

Where to Stay – Castellina in Chianti Hotel

I’d recommend booking at Hotel Palazzo Squarcialupi for its excellent, walkable location, spacious rooms and glimmering pool. Located just underneath Taverna Squarcialupi, you can have your complementary breakfast with a view each morning as you watch the sun rise high over the sprawling hills. It doesn’t get much better!

In conclusion, Castellina in Chianti is a haven for those seeking an authentic Tuscan experience. Its rich history, exquisite wines, mouthwatering cuisine and breathtaking landscapes create an irresistible blend of charm and allure not to be missed on any Italian getaway.

Related Links:

Staying in nearby Florence? Check out my list of the best rooftop bars for a unique perspective on the city.

Without a car but still longing for those panoramic views? Consider booking this highly-rated Chianti wineries tour from Florence.