Rooster sculpture on display outside a restaurant in Italy.

Castellina in Chianti – All You Need to Know for Your 2024 Visit

Are you trying to decide if you should fit Castellina in Chianti into your Tuscany itinerary?

We live nearby and I’ve been visiting for work and play since 2004.  Castellina is a pleasant stop for a half-day (or even a really leisurely day) and it pairs well with a visit to other Chianti village. 

It’s a lively little village, full of restaurants and small shops, and it doesn’t really shut down during lunch time, which is nice if you still want to check out the shops or explore during the afternoon hours.

This is my guide to Chianti, which includes what to do, where to eat, where to stay, and tips like where to park.  Note that it’s not a complete list of every single thing you can possibly do in or around Castellina.  Instead, this is our short list that we use when we bring visiting friends or family or stop in if we’re out exploring. 

Andiamo – let’s go!

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Where is Castellina in Chianti?

Castellina in Chianti is… in the Chianti area of northern Tuscany in central Italy. 

Together with five other villages (Radda in Chianti, Panzano in Chianti, Greve in Chianti, Gaiole in Chianti, Castelnuovo Berardenga), it makes up the most famous part of the Chianti Classico region.

Legend of the Black Rooster:  If you’re visiting any of the Chianti Classico villages, or drinking Chianti Classico wines, you’ll notice the black rooster – gallo nero.  It’s the symbol of the League of Chianti (historically) and the Chianti Classico. 

Legend says that in medieval times, when Siena and Florence were constantly battling over the border between the two, they finally decided to put an end to the fighting.  Each city would choose a knight on horseback to depart their respective cities at dawn and wherever the two met, the border would be drawn.  With no alarm clocks, they used a rooster to signal the start of the day (and the ride).

The Sienese chose a white rooster and fed it will and took care of it until the day of the ride.  The Florentines chose a black rooster and starved it and kept it in a small, dark coop until the day of the contest.

When the day of the ride arrived, the sneaky Florentines freed their hungry and confused rooster and it began its ‘cock-a-doodle-doo’ immediately, way before dawn.  As that was the signal to ride, the Florentine knight began, much before the Sienese horse and knight, who began when their rooster called out at dawn.

The two met in Fonterutoli, close to Castellina (and very close to Siena), which gave Florentines a much larger part of the Chianti region.

And now, you’ll notice the black rooster wherever you go in Chianti Classico!

Who Will Love Castellina in Chianti

Castellina is perfect for:

  • Wine lovers – sample and purchase Chianti Classico and other area wines in town and at nearby wineries
  • Families – the village center is a pedestrian zone and small enough to wander around with kids for a little while; there’s also a small playground for young children
  • Those who are looking for a small, lively village that doesn’t close up during lunch time
  • People who want to see beautiful views of the countryside – especially from the top of the fortress tower!

Read our guide to Castellina with Kids

Who Should Skip a Visit to Castellina in Chianti

  • Anyone looking for a big city – Castellina is tiny
  • Visitors wanting a Michelin-star meal – there are plenty of great eateries in Castellina, but none are fancy

When to Visit Castellina in Chianti

You can visit Castellina year round, but I find the village is at it’s best from spring (April-ish) through fall (mid to late-October), when shops and restaurants are open, there are events and festivals running, and visitors give the village a lively atmosphere.

Castellina can be very hot in the summer, so avoid mid-day visits and instead come for a stroll and aperitivo or dinner in the evening. 

Winter in Castellina is quiet, but you can still stop in at some restaurants and wineries.  

Read more about Tuscany in the SpringSummerFallWinter.

Top Things to Do in Castellina in Chianti

Walk the Via delle Volte

Restaurant set up in the Via delle Volte in Castellina in Chianti. You can see the waiter speaking with a couple at their table.
Inside the Via delle Volte

The Via delle Volte is an underground medieval passageway along Castellina’s city walls that was once used for both military and religious reasons.

You can walk along it (it only takes a couple of minutes) and peek out the windows to see the spectacular countryside. 

It’s a nice place to walk on a hot summer day, and you can even stop for a cold drink or a meal at the restaurant along the passageway – Ristorante Sotto Le Volte. 

Fun Fact:  The passageway wasn’t always covered.  As the town grew, buildings were added on top of it. 

Taste Wine at an Enoteca

Wine and olive oil bottles on display inside an enoteca.
The shop and tasting area at Enoteca Squarcialupi

You’re in the Chianti Classico wine region, so it would be silly not to try any of the area’s wines. 

There are multiple enoteche (wine bars / shops) around Castellina, and I usually find myself at Enoteca Squarcialupi on the main drag.  You can taste wines by the glass or you can purchase a wine card and use it to get pours from the machines.

Most days you can also get light snacks like focaccia, and if you have time, visit the cellar below the shop!

A visit to the enoteca is easy to combine with its restaurant next door – Taverna Squarcialupi.

Helpful Tip:  If you know you’d like to do a tour and tasting at the Enoteca Squarcialupi, call ahead and reserve.

Climb the Castle Tower

Castellina’s castle was built by the Florentines, who wanted to strengthen their defenses against the Sienese to the south. 

There is a small museum at the base of Castellina’s castle.  Pay to enter because it includes the climb up the tower, which has incredible views of the Chianti countryside. 

Have an Outdoor Meal

View of table and countryside from the terrace at Taverna Squarcialupi in Castellina in Chianti.
The outdoor terrace at Taverna Squarcialupi

One of my favorite things to do in Castellina in Chianti is have a meal on the main piazza, outdoors along the pedestrian street, or on an outdoor terrace with a view of the countryside. 

You have quite a few options in Castellina, and I’ll list some of my favorites below.

While lunchtime is lovely, Castellina is extra charming in the evening.  If you can, have aperitivo and/or dinner in the village.

Browse the Shops on Via Ferruccio

Front entrance to enoteca and food souvenir shop in Castellina in Chianti, Italy. There are displays set up outside the shop.

The main drag in Castellina in Chianti is the pedestrian street, Via Ferruccio, which runs for about 150 meters and is full of little shops and boutiques selling wine, food treats (like pasta, jarred sauces, and spices), clothing, souvenirs, linens and homewares.

Go For a Romantic (or Quiet) Walk Along the Village Walls

Paved path outside the walls of Castellina in Chianti. You can see olive trees and vineyards to the left.

Walk just outside the walls and you can have nice views of the countryside below all to yourself (or with just a few people). This little paved path is perfect for an afternoon stroll or an evening passeggiata.  It’s just a couple hundred meters, but it’s a nice tranquil place in the lively village.

See the Church of San Salvatore

San Salvatore church on the main piazza in Castellina in Chianti

Castellina in Chianti’s main church dominates the square at the entrance of the historic center.  Step inside and see the relics of San Fausto, a local farmer and martyr who stood up to the Romans and refused to renounce his Christian faith.  San Fausto is the patron saint of Castellina in Chianti and there’s a festival honoring him each fall.

Where to Eat in Castellina in Chianti

Outdoor terrace at Albergaccio di Castellina restaurant. You can see potted plants and terracotta ground.
Albergaccio di Castellina’s outdoor dining area

You have quite a few choices in Castellina, so feel free to check out menus and find one with dishes that appeal to you.

A few of our favorites include:

Taverna Squarcialupi is our go-to in town for typical Tuscan fare in an excellent setting.  Ask for a table on the back terrace and enjoy the vineyard and countryside views.  Great with kids and dietary restrictions.  Try the pici pasta with ragù al cinghiale (wild boar sauce). 
Via Ferruccio, 26. +39 0577 741405

Ristorante Sotto le Volte is the place to go for lunch on a hot summer day.  The restaurant is located under the village on the historic Via delle Volte.  Also a nice spot for a glass of local wine and a tagliere of cured meats and cheeses. 
Via delle Volte 14/16. +39 0577 741299

Osteria il Re Gallo has a perfect spot on the main piazza of Castellina.  Classic Tuscan dishes and friendly service!  Best to reserve for dinner.
Via Toscana, 1. +39 0577 742000

Albergaccio di Castellina is a small restaurant just outside of town with delicious ‘Tuscan with a twist’ fare.  The restaurant used to have a Michelin-star, but it’s not stuffy at all.  This is a great choice for a romantic evening dinner or a nice lunch with friends.  I love the terrace if the weather is nice – it’s pleasant even on a hot summer day because it’s shaded, and you get gorgeous views of the countryside below.

There’s a little gravel parking lot out front, or you can park on the street.  Call ahead to reserve, especially if you’re visiting in spring, summer, or fall – but you can also try to drop in.
Via Fiorentina, 63. +39 0577 741042

Pizzeria il Fondaccio is the place to go for pizza in Castellina in Chianti.  You can sit outdoors on the main drag and wash your pizza down with fine Chianti wine!
Via Ferruccio, 27. +39 0577 741084.

I’ve heard good things about the Altrochè Wine Bar di Rocca delle Macie, just outside of town.  Sample wines while you have simple dishes like panini or meat and cheese platters.
Viale IV Novembre, 23. +39 0577 732299.

Gelato can be found on the main street of Castellina, or drive or walk the 600 meters down the road to Gelateria di Castellina.  It’s some of my favorite gelato – all homemade and they use seasonal ingredients like blackberries or figs to make creative flavors.  Plenty of classic flavors too.  The lime/basil is a hit, but there are so many more worth trying.  Don’t miss this gelateria – it’s a must-stop, and one of the best in Tuscany.

Good To Know:  Need to hydrate?  There’s a water fountain in the main piazza with the church.

Where to Stay in Castellina in Chianti

I recommend staying at a hotel or agriturismo in the countryside around Chianti if you have a car.

You may want to check out:

Il Borgo di Vescine – Beautiful hotel in an intimate setting; classic Tuscan décor; magical dinners in the olive grove; cooking classes and wine tastings; swimming pool with an epic view.  I’ve always enjoyed my stays here. Il Borgo di Vescine – info and rates.

Hotel Colle Etrusco Salivolpi – A countryside hotel just outside of Castellina; easy to walk in to Castellina along the road; other restaurants nearby. Hotel Colle Etrusco Salivolpi – info and rates.

Tenuta di Lilliano – A working wine estate and agriturismo; villa and apartment rentals for self-catered stays; pools with spectacular views of vineyards, olive groves, and forested countryside; simple, classic Tuscan décor.  Tenuta di Lilliano – info and rates.

Castello di Fonterutoli – I love the design in the rooms here – simple, Tuscan ‘with a twist;’ you’re part of the borgo, which includes the winery, enoteca, and restaurants; swimming pool with a view. Lovely place to base yourself during the vendemmia. Castello di Fonterutoli – info and rates.

Things to See & Do Near Castellina in Chianti

Main piazza in Monteriggioni, Italy on a sunny day.
  • Go wine tasting at Fonterutoli, Castello di Meleto, Castello di Ama, Castello di Albola
  • Visit other Chianti villages like Radda in Chianti or Panzano in Chianti
  • Take a dip in the Elsa River and check out the Diborrato waterfall
  • Walk the walls of medieval Monteriggioni
  • Spend time in Siena
  • Explore tiny Volpaia and taste its wines
  • Go for a hike in the Chianti forest (but not during hunting season)
  • Visit Badia a Passignano
  • Look at outdoor art at the Chianti Sculpture Park and nearby Pievasciata

How to Get to Castellina in Chianti

Driving to Castellina in Chianti

The best way to get to Castellina in Chianti is to drive your own car.   

If you’re not arriving from somewhere else in Chianti, you’ll likely want to take the superstrada that runs between Florence and Siena and exit San Donato (if coming from the north) or exit Monteriggioni (if coming from the south).

You can also drive the Chiantigiana, the smaller country road that connects Florence and Siena.  The scenery is gorgeous and you’ll pass small villages, vineyards, olive groves and forested land.  While beautiful, it takes longer than the superstrada and you’ll have more winding, narrow roads.

Parking – There are a few parking lots.  The two I prefer are lot #3, just below the center, and the lot outside the village.  Lot #3 (on map) is more convenient, but it’s smaller.  You can try it, and if it’s full, just head back out of the village and drive to the other lot.  It’s about a 5-10 minute walk to town from the large lot outside the village.  The parking is pay and display.  Lot #3 has a pay toilet.

Good To Know:  There’s a punto panoramico (panoramic viewpoint) on the road between San Donato and Castellina, closer to Castellina.  It’s marked with a brown sign and there’s a small pullout.  On a clear day, you can even see the towers of San Gimignano! 

Good To Know:  There is a ZTL (limited traffic zone) in the historic center of Castellina in Chianti, but there’s a warning sign before you get to it, and you can easily turn right to avoid it.

Taking the Bus to Castellina in Chianti

It’s not bad taking the bus from Siena to Castellina – about an hour, and there are multiple buses daily. 

Florence, on the other hand, is a little more of a pain – it involves changing buses and takes a lot longer (over 2.5 hours).

Taking a Day Tour to Castellina in Chianti

If you don’t want to worry about driving, navigating, or parking, you can take a day tour like this Chianti Half-Day Tour from Florence.

Having a Private Driver Take You to Castellina in Chianti

Another option is to hire a private driver to take you to Castellina or even on a Chianti tour that includes some of the other Chianti villages.  While more expensive, it’s a relaxing way to enjoy the countryside – and you can enjoy your wine tastings!

Read more about
Renting a Car in Tuscany
Tuscany Without a Car

Cycling to Castellina in Chianti

The area around Castellina is prime cycling country, so if you enjoy riding, rent a bike and tackle the Chianti hills. 

Fun Fact:  My first date with my husband was a bike ride in this area and we stopped in Castellina for gelato!

Castellina in Chianti FAQ

Is Castellina in the Chianti region?

Yes, Castellina is in Chianti – it’s even in its name!  Castellina is part of the smaller sub-area, Chianti Classico.