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Four Days in Tuscany with Kids

Tuscan sunset with kids

Tuscany is at the top of most bucket lists.   Walking through quaint hilltop villages, driving through the green and yellow landscapes of the Val d’Orcia, tasting wine in a farmhouse while eating the most delicious homemade pasta- it all sounds perfect, right? 

Now imagine taking your children, too.  Wait, before you get anxious and start assuming I’m crazy, hear me out.  You can do all of these things while on a family vacation. If you don’t believe me, read along; I have the perfect four day itinerary for Tuscany with kids. You and your kids will spend four days visiting idyllic villages, having a picnic at a farm, and enjoying the laidback pace at your villa.

Tuscany is great for young families.  There are plenty of little villages to discover, but with endless open space for little ones to run around. While there is more than enough to do, the hillsides are perfect for afternoons of doing nothing but soaking up the Tuscan sun.  We were only able to spend four nights in Tuscany, but we easily could have spent a week or more.  It was such a nice change of pace after the hustle and bustle of Rome, and our stay allowed us some downtime to recharge our batteries before continuing on to Positano.  

Val d'Orcia | Pienza
Val d’Orcia | Pienza

We opted to take our trip to Italy in April, which left us with the most perfect weather.  Most days started off with a slight chill and warmed up nicely as the sun came out, allowing us to enjoy afternoons outdoors.  Summer does get very hot, so consider staying somewhere with a pool if that is when you plan to go.

Tuscany with kids is best approached with a slower pace in mind.  Plan to spend your mornings exploring one of the many picturesque towns, walking around and taking in the sights or enjoying an espresso at a cafe while your kids run around in the town square.  Every town usually has a playground or park so let them burn off some energy before finding a place for lunch.  Then enjoy the quiet while they nap in the car and you drive around taking in the beautiful sights of the countryside.  Spend the evenings at your farmhouse and enjoy the family time free from schedules. 

Getting To & Around Tuscany with Kids

There are two options for getting to Tuscany: train and car. However, a lot depends on where you are staying and where you are coming from.  We were coming from Rome, so we chose to take the train into Chuisi- the large town closest to our farmhouse that had a train stop and car rental- then pick up a rental car.  You could drive from Rome, but the traffic there is terrible , so picking up your car in Tuscany is the easier option.  

A car is pretty much required for getting around in Tuscany. End of story.  Most of the area is not well connected by the train system.  The Italians never took up the challenge of running tracks over and around to the hillside towns.  They were probably doing something more fun like drinking wine and eating pasta.  This also allows you to come and go at your own pace between towns.  Car naps will be a great way to spend the afternoon, allowing you to take in scenic drives. 

bikes in Tuscany
village scenes

Just a note about carseats; we didn’t want to carry ours around for 12 days, knowing we would only need them for these four days of our trip.  We rented the seats from Hertz and had no issues.  The car seats were perfectly clean and in great condition.  

Our car came with a GPS, but we never used it having previously had bad luck in other countries.  Often these are outdated, and the spelling differences between English and the local language can cause major frustration when inputting destinations.  Instead, David spent a few minutes every morning getting a general feeling for our route using the wifi in our apartment.  We also rented a mobile hotspot for our entire trip to allow for use of google maps, but with sometimes questionable reception we didn’t want to rely on it.  

Where to Stay  in Tuscany with Kids

There are so many options for Tuscany, but the most common is a farmhouse or villa stay.  Depending on the size of your group, you can find several options.  Make note that many places only allow for stays in weekly increments, especially during the summer months.  The best advice I can give is to decide what villages you think you will want to visit then decide on a somewhat central location for your accomodation.  We knew we weren’t going to venture up to Florence or Siena, so we chose a place a little farther to the south.  This allowed us to easily get to most of the small towns we aimed to see within 45 minutes or less.  

Chiarentana - Tuscany with kids
afternoons at La Chiarentana

We considered so many different lodging options for Tuscany.  We finally landed on a farmhouse apartment at La Chiarentana.  It is the sister property of the famed La Foce estate.  La Chiarentana was the perfect place and location for our stay. Our apartment was huge with sprawling grounds for afternoons spent exploring.  I would highly recommend staying here.  
Some others that we considered (if you need more options or just inspiration) are listed below.  While I can’t personally speak to these properties, they have great reviews and are all kid friendly.

  • Fonte De Medici
  • Borgo Scopeto
  • Al Gelso Bianco
  • Borgo Lucignanello Bandini

A few tips for Tuscany with Kids

  • Tuscany is best enjoyed at a slower pace.
  • Get the children excited to “explore” the towns.  Come up with a fairytale related to the town or make the actual history a little more kid friendly to make it more fun for them.
  • Strollers-  The streets in all of the towns we visited are easily navigated with a stroller.  One thing to note is the hills, especially in Montepulciano.  We used strollers in every town.  It was tough to go up the hills, but I figured it was easier than carrying them up.  We used the bottom basket for water bottles and diapers so I didn’t have to carry around a huge bag all day. Our daughter did enjoy getting out and walking a lot, as well.  I would suggest taking a baby carrier for smaller babies. It was nice to have on hand for touring churches and going up into bell towers, etc.   
  • Restaurants and shops may close midday so if there is a place you really want to try make sure to verify their opening hours.  We found that in the smaller towns this was much more prevalent.  There is usually always at least one place open, although it may not be what you were hoping for. 
  • Wine in the region is often a table wine.  The prices are ridiculously inexpensive, so buy a bottle with meals and take the leftover with you.
Montalcino Fortress with kids
baby carrier for the win at the Montalcino Fortress

Day 1 in Tuscany with Kids


Arrive via train and retrieve your rental car.  For us, the best option was a train into Chiusi, only about 30 minutes from our farmhouse.  The Hertz rental car was directly across the street.

Depending on your arrival time, you can spend the morning exploring any towns on the way to your accommodations.  We ended up just driving around the countryside for the morning taking in the scenery.  After an hour or so, we made our way to Montepulciano.  We were ready for lunch so after exploring for a bit, we made our way to Pentolaccia.  We ordered a bottle of local Vino Nobile di Montepulciano, a charcuterie plate of local cuts of beef and wild boar, a few pasta dishes and spent the lunch hour in food heaven.

Lunch and Playtime in Montepulciano

After lunch and any more exploring (we planned to come back another day so we only stayed in town for about an hour), stop at the grocery before leaving town to stock up on all the essentials you will need. The grocery store in Montepulciano is large and has everything you need.  Make sure to stop at the playground at the base of the town to let the kids play for a bit.  There is a little fort with slides, seesaw, and a few swings. 

Montepulciano playground - Tuscany with kids
play time in Montepulciano

Laidback Evening

Check in to your accommodations.  We stayed at the beautiful La Chiarentana.  This place was everything I imagined for a stay in the Tuscan countryside.  Spend the evening eating dinner, playing outside, and checking out the grounds.  

Day 2 in Tuscany with Kids

Village Exploration

Start your day in San Quirico d’Orcia.  Once an extremely important stop on the Via Francigena, a pilgrimage route connecting Europe to Rome in ancient times, this little village still has most of its fortified walls still standing.  Make sure to check out the Collegiata of the Saints Quirico and Giulitta, a beautiful Romanesque church built in the 11th century.  Located behind the Church of Santa Maria Assunta, is an entrance for the Horti Leonini gardens, an  example of symmetrical Italian renaissance gardens.

Leisurely Lunch

After checking out the town, you’ll probably be ready for some lunch.  Get back in the car and drive about 20 minutes toward Montalcino.  Right outside of town, in a sharp curve there is a driveway for an unassuming farmhouse restaurant.  Locanda Demetra was one of our favorite and most memorable meals in Tuscany, and possibly all of Italy.  If you can snag a table here, do yourself a favor and spend a couple of hours.

Locanda Demetra Tuscany
our favorite restaurant in Tuscany | Locanda Demetra

Val d’Orcia Views

 After the delicious lunch, make your way into Montalcino for the afternoon.  The first walls of the city were built in the 13th century.  The fortress, one of the most dominant visual aspects of the village, was built in a pentagonal shape at the highest point in the village.  You can still go up and walk the ramparts for a small fee (paid just inside at the wine store) enjoying views of the oak trees, olive groves and hills of the Val d’Orcia.  Spend some time checking out the town, especially the Palazzo Dei Priori and its clocktower, located in the Piaza del Popolo.  We arrived around 1:00pm, so many places were actually closed for riposo (the Italian version of siesta), but we enjoyed this as town was quieter.

view from the Montalcino fortress
view from the Montalcino fortress

Montalcino is most famous for its Brunello di Montalcino, so be sure to enjoy a glass (or bottle) with lunch or dinner.  It is worth noting, these wines are relatively inexpensive while in the area, but the prices skyrocket once you get into areas outside of Tuscany.  So drink up if you enjoy these wines 😉

Tuscan Sunsets

After seeing everything in Montalcino, make your way back to the farmhouse for dinner and playtime. We opted to pick up a bottle of local wine and watch the sunset.  It was the perfect ending to a great day.  

sunset at La Chiarentana
sunset at La Chiarentana

Day 3 in Tuscany with Kids

Explore Monticchiello

Start the day with a quick drive to Monticchiello.  This quiet town doesn’t have much going on in the way of tourism, but it gave a glimpse into modern life in a small historic Tuscan village.  We saw a few local boys stop at the tourism office to sneak in some computer time.  We peeked into the beautiful churches in town and spent about 45 minutes here in total.  

Continue on to Montepulciano.  We knew after making a quick stop on day one that we wanted to come back here, and it ended up being one of our favorite towns in Tuscany.  It is a true midieval walled city.  The town of Montepulciano gained quite a bit of power during the 14th and 15th centuries.  This peaked in the 16th century when the famous Medici family came into power. The expansive buildings and residences in Montepulicano are evidence of said power and wealth, especially when compared to some of the smaller, simpler buildings in other villages.  

Montepulciano is, by far, the hilliest town we visited so be prepared for some serious uphill treks.  Parking is located at the bottom of the hill outside of town; make sure to wear comfortable shoes.  

stroller in Montepulciano - Tuscany with kids
Montepulciano hills are no joke!

Make your way up to the main piazza, checking out the shops and smaller churches along the way.  Once you reach the Piazza Grande, you can check out the many buildings and churches in the center of town.  

Duomo di Montepulciano -Tuscany with kids
on the steps of the Duomo di Montepulciano

After wandering around a bit, make your way to the park for a picnic lunch.  Facing the Duomo (church), take the road to the right and head south.  This leads to a small green space with a play area for children.  We stopped at a small bakery and picked up a few sandwiches and sweet treats for a laid-back lunch.  Then, we let the kids spend a bit of time playing.

Garden Tour and Dinner

In the afternoon, go to La Foce for an afternoon tour of the gardens.  The tour only lasts about 45 minutes, so it is done fairly easily with kids.  Afterwards, go for a casual outdoor dinner at Dopolavoro La Foce.  They have a full service restaurant inside, but we were headed straight outside for the beer garden.  They have hammocks, ping pong tables, and plenty of open space for an evening outdoors.  

Dopolovoro La Foce - Tuscany with kids
laid back afternoon at Dopolavoro La Foce

Day 4 in Tuscany with Kids


Start your day in Pienza, the most idyllic Tuscan town we visited.  It is exactly what you imagine when conjuring up daydreams about Tuscany, and it is rightfully called the “ideal city of the Renaissance”.  Perfectly perched atop a hill, it is approched via winding roads of the Val d’Orcia.  Once a humble town, Pope Pius II used his wealth and power to transform his home village into the town we see today.

While we were there, we all were fascinated with watching four little old men repair an area of the Piazza Pio II.  They were replacing stones by hand, using only shovels as tools.  They were definitely on Tuscan time, avoiding getting into any kind of hurry.  From the piazza you can wander the relatively flat streets, discovering the alleys and shops.  Pienza is famous for its Pecorino, so be sure to stop in a shop and admire all the rounds of cheese.

Farm Visit and Picnic

After seeing all you want to see in Pienza, drive to Podere Il Casale for an afternoon at a local farm with a picnic lunch.  Spend a few hours relaxing, eating, and watching the animals.  Then make your way back to the farmhouse for an evening of family time before you leave this beautiful area.  

lookout at Podere il Casale -Tuscany with kids
lookout at Podere il Casale

This four day itinerary can obviously be changed to accommodate your schedule and location. The main point is to make sure to just relax and enjoy being in Tuscany! This was, by far, one of our favorite trips we’ve taken with the kids to date. I know we will have more great adventures in the future, but I cannot imagine many that will top this little slice of heaven. You will not regret taking this amazing vacation with your kids!

Looking for more of our trip? Check out this post on Positano with kids.

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  • Reply
    Karissa Barcelo
    May 9, 2023 at 11:40 pm

    We just got back from Tuscany with our 2 year old. Absolutely loved the culture, the food, the people! Great blog.

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