Pedestrian center of Castellina in Chianti in Tuscany, Italy. You can see stone buildings and in the foreground a restaurant with an outdoor eating area.

Castellina in Chianti with Kids – The Best Things to Do with Your Family

If you’re staying in Tuscany with your kids and decide to visit Chianti, add Castellina in Chianti to your itinerary.  It’s a small village to stop in for a quick stroll, some time at the playground, or to have a meal outdoors.

While it’s not a destination I’d go out of my way to visit on a family trip, there are a few things to do to keep kids and adults happy for an hour or two.

I live in Tuscany and have been exploring Chianti (and Castellina) since 2004.  Here are my top things to do with kids in Castellina in Chianti, plus a few tips to make your visit smooth.

You may also want to read my general post on Castellina in Chianti.

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Where is Castellina in Chianti?

Castellina in Chianti is in the Chianti Classico area of northern Tuscany.  It’s between Florence and Siena (a little closer to Florence) in the hilly area full of forest and vineyards. 

Click on the icon in the upper left to see the points of interest for Castellina with kids.   You can also see the black markers that pertain to the legend of the black rooster (story below).

Reasons Visit Castellina in Chianti with Kids

  • Castellina has a stroller-friendly pedestrian center so your don’t have to stress about cars and traffic (although you still need to watch for the occasional local resident or business vehicle)
  • The village doesn’t shut down in the afternoon, so you can stop by any time of day and find something to see or do
  • There’s a shady and gated playground in town
  • Castellina has a few restaurants that have outdoor seating and are kid-friendly

When to Visit Castellina with Kids

For a family visit to Castellina, try to plan for the spring or fall, or for the summer in the evening.  It gets toasting in Castellina in Chianti during the summer, and the winter can be a little too quiet for a visit with kids.

Helpful Tip:  If you do visit on a summer day with kids, walk the Via delle Volte, have an outdoor (shaded) meal, get gelato, and keep your water refilled using the fountain in the main piazza.

Best Things to See and Do in Castellina with Kids

Look for Black Roosters

If you haven’t told your kids the story of the black rooster (gallo nero in Italian), make sure they know it before they get to town (or even Chianti).  They’ll have fun spotting the black roosters in the Chianti Classico area in towns and on the region’s wine bottles. 

So, what’s the deal with the black rooster?

Well, the legend is that in medieval times, when Siena and Florence (both marked on the map above) 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!

In each of the Chianti classico towns, you’ll find a large black rooster statue. 

In Castellina in Chianti, it’s located in the small paved area with a viewpoint at the main intersection in Castellina.  There are also other black roosters in town (art and on wine bottle labels) – have your kids look for them!

Visit the Playground in Castellina

Colorful playground and trees in Castellina in Chianti, Italy.

Castellina’s playground is just outside the village walls, and worth a visit if you’re traveling with small kids.  The playground is shady, so it’s perfect on a hot day.  There are benches, the ground is padded, and there are a few small toys for little kids (it’s not amazing for older kids).

Walk 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.

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. 

Climb the Tower

Pretend you’re a knight!  Climb up to the top of Castellina’s tower and check out the views of the Chianti countryside. 

There’s also an archaelology museum (same ticket) and there are occasional kids workshops organized in English.  Check the Museo Archeologico del Chianti Senese official website for the latest hours and workshop info.

 Attend a Sagra

Posters for sagre and festivals on a wall in Tuscany, Italy.

Castellina is tiny, but there are events throughout the spring, summer, and fall.  You can check in with tourist info, or if you’ll be in Chianti for a few days, look at the posters hanging up around the village.

Check out the Church in Castellina

San Salvatore church on the main piazza in Castellina in Chianti

Older children may be interested in learning about relics and seeing the body of San Fausto on display in the Chiesa di San Salvatore on the main piazza.  San Fausto is Castellina’s patron saint.  If you’re in town in September, check the dates of the multi-day celebration that honors him.

Stop in at an Enoteca

Wine and olive oil bottles on display inside an enoteca.
Enoteca Squarcialupi

I know, I know – wine tasting isn’t for kids!  But, if you have adults in your group who want to try wines, you can sample vino while your little ones nibble on bread, cheese, and salame (or nap in the stroller). 

Enoteca Squarcialupi has a small area with barstools where adults can taste wines while kids  color or sample the finger foods (like focaccia). 

There’s another enoteca on the main street that also sells food souvenirs, so your kids can help choose a pack of dried pasta or a new spoon while you choose the wine for your dinner.

Good To Know: There are a lot of wineries around Castellina in Chianti that make for great stops during the grape harvest in the fall.

Where to Eat with Kids in Castellina in Chianti

Osteria il Re Gallo has a perfect spot on the main piazza of Castellina, so you can eat outdoors and then your kids can play in car-free piazza while you finish your meal.  Classic Tuscan dishes and friendly service!  Best to reserve for dinner.
Via Toscana, 1. +39 0577 742000

Taverna Squarcialupi is our go-to in town for typical Tuscan fare in an excellent setting.  They’re great with kids, and both the outdoor terrace (amazing views!) and the indoor dining room (huge wine barrels!) work with kids.  No kids menu but you can order a mezza porzione (half-portion).  Last time I was here there were three families with strollers having lunch on the terrace.

You can also combine a meal here with tour of the cantina next door. 

Via Ferruccio, 26. +39 0577 741405

Ristorante Sotto le Volte is located under the village on the historic Via delle Volte.  
Via delle Volte 14/16. +39 0577 741299

Gelato – There’s a nice gelateria in town, which is convenient if you want to stroll while you eat.  Otherwise, hop in the car and drive (or walk the 600 meters) just outside town to Gelateria di Castellina.  It’s worth the trip for the homemade gelato that uses seasonal ingredients.  I will drive out of my way to get gelato here – it’s one of the Best Gelaterie in Tuscany.

Good To Know:  It’s easy to get high chairs in Castellina.

Where to Stay in Castellina with Kids

Horse peeking out of stone stable in Tuscany.
Kids can say hi to the horses at Castello di Fonterutoli

The center of Castellina is lovely, but if you’re in Chianti with kids, I highly recommend staying at an agriturismo or hotel in the countryside – somewhere with a pool and some green space so your children can run around and play.

Here are some places you may want to check out for your family:

Tenuta di Lilliano – The wine estate and agriturismo has multiple apartments for rent.  The style is classic Tuscan, and it’s a great base for exploring Chianti with your family.  Swimming pools, wine tastings.  Tenuta di Lilliano – 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.

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.  No large green space, so probably best with older kids if you’ll be spending a lot of time at the property.  I’ve always enjoyed my stays here. Il Borgo di Vescine – info and rates.

Castello di Fonterutoli – No castle to be seen anymore, and there’s not a lot of green space, but there are on-site restaurants and horses (privately owned, so no horseback riding available)! Pool is a couple of kilometers away. Castello di Fonterutoli – info and rates.

Castellina in Chianti with Kids Basics

Pedestrian street in Castellina in Chianti. People are walking and also sitting outdoors under umbrellas at a restaurant.
Pedestrian street in Castellina

Strollers – Castellina is stroller-friendly.  If you need a place to walk baby to sleep in the stroller, walk on the path outside the town walls. 

Diaper Changes – You can change diapers in restaurants or cafés, or find a bench and use your portable changing mat.  There are a couple of pay toilets but they don’t have changing tables and they haven’t been in great shape when I’ve seen them.

Pharmacy – There’s a pharmacy on Via Ferruccio, the main drag.

Grocery Store – There’s a tiny Coop in town (just outside the ZTL).  If you need a larger grocery store with more selection, you can shop at the Coop in San Donato or bigger stores in Poggibonsi, Siena, or Greve in Chianti.

Water – Refill your water bottles in the fountain by the main square and San Salvatore Church.

Traffic – The main street (Via Ferruccio) and piazza in Castellina are pedestrian zones, but of course, there can always be the occasional local car driving through.

Parking – If you have a stroller or a lot of kids with you, try to park in the lot below town first (marked on map).  If it’s full, you can drop your group off and drive to park in the lot outside of town. 

Family-Friendly Things to See & Do Near Castellina

Boy making fresh pasta shapes and setting them on a drying rack at a cooking class.
My son making pasta at Toscana Mia’s cooking class
  • Let your kids explore Castello di Brolio while you taste Chianti Classico wine
  • Walk the walls of medieval Monteriggioni
  • Spend time in Siena
  • Join a kid-friendly cooking class with Toscana Mia
  • Look at outdoor art at the Chianti Sculpture Park and nearby Pievasciata
  • 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
  • Cycle the Chianti hills (best for older kids who are experienced cyclists)
  • Explore Tuscany’s medieval Manhattan, San Gimignano
  • Go on a kid-friendly wine tour that goes into a vineyard and inside the cantina
  • Have a summer evening meal in San Donato in Poggio
  • Look for wild boar in Greve in Chianti

Enjoy your visit to Castellina in Chianti with kids!

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