How to Spend 2 days in Tuscany Countryside With Kids
Are you planning to visit the Tuscany countryside with kids? You are in for a treat! In this post, I share exactly how we spent two days in Tuscany’s Countryside with our two kids, and much of that time was spent relaxing and eating delicious food!
Last summer, we visited Italy for 10 days and immediately fell in love with it. I believe it is one of the most family-friendly places we have visited. We explored Rome, Florence, Pisa, and Cinque Terre and then headed to Tuscany’s countryside to unwind and get lost in the Cypress Trees and magical sunsets before returning home.
Our goal was to avoid too much sightseeing here and wanted to focus on resettling and relaxing.
We explored the pretty little towns of Montepulciano, Montichiello, and Pienza. We tasted the most incredible authentic food, enjoyed lovely Valdorcia views, and relaxed at a family-friendly hotel.
This little getaway was exactly what our family needed to complete our first trip to Italy! Let’s Dive in.
Why Visit Tuscany With Kids
Imagine rolling hills, charming villages, and endless vineyards that create a peaceful escape where you can slow down and breathe. Simple joys—like fresh cheese, friendly smiles, and stunning sunsets—make you feel truly alive and connected.
Visiting here isn’t just about seeing beautiful places; it’s about feeling connected to the land, the people, and yourself.
Kids will have a lot of space to run and explore safely. They can see animals on farms, try yummy local foods, and have fun learning about history in a way that feels like an adventure.
The slow, calm pace means families can spend more time together, enjoying picnics, visiting castles, and watching beautiful sunsets. It’s a perfect spot to make happy memories with your kids.
Getting to Tuscany’s Countryside
The easiest way to reach Tuscany’s countryside is by car, allowing you to explore hill towns like Pienza, Montichiello, and Montepulciano at your own pace.
Alternatively, you can take a train from Florence to nearby towns such as Siena or Montepulciano (with a bus connection),
If you are visiting from Rome, the fastest option is to take a high-speed train to Florence (about 1.5 hours), then rent a car to reach the countryside.
We rented a car in Rome and parked it until it was time to leave. We then drove to Florence, stayed four days, and continued to Tuscany’s countryside.
Tuscany’s small towns, like Pienza and Montepulciano, have narrow streets and limited parking in their historic centers. Travelers should look for blue-lined spaces for paid parking and avoid yellow or white spaces, which are usually reserved for residents or specific uses.
Important reminders:
- Carry cash or a contactless card for parking meters.
- Many rural roads are winding and may lack lighting at night.
- Italian road rules require headlights outside towns, even during the day.
- Renting a compact car can make maneuvering through villages much easier
Where to Stay in Tuscany’s Countryside With Kids
I highly recommend staying in the Val d’Orcia region for a magical family getaway—think charming towns like Monticchiello, Montepulciano, Bagno Vignoni, and Pienza.
These spots offer the perfect blend of rolling hills, open spaces, and authentic Tuscan charm, where children can explore freely and soak up nature.
Stay at a Family-Friendly Hotel
Many family-oriented hotels and villas are spread throughout Tuscany’s rolling hills and vineyards. These facilities include pools and spacious family suites.
During our 2-night family getaway to Tuscany’s countryside, we stayed at the beautiful Hotel San Gregorio in Pienza. The hotel is ideally located near Monticello and Montepulciano;
We loved it because it offered budget-friendly, comfortable family rooms, a crib, and an AC unit, which was very important to us.
The location was ideal as well. We were a short drive away to explore the streets of Pienza, Montepulciano, and Monticello.
Note: If you plan to visit in the summer, like we did, ensure your hotel/villa has AC. We visited. You must also request any extra beds/cribs before your arrival.
The hotel’s tranquil garden and large pool were exactly what we needed to unwind and let the kids enjoy some downtime.
Stay at Agriturismo
Staying at an agriturismo is another excellent way to experience the Tuscan countryside with kids.
Agriturismos are working farms that offer accommodation and often meals to visitors. They provide a unique way to experience the Tuscan countryside by staying on a farm where guests can enjoy fresh, local food like olive oil, wine, cheese, and vegetables grown right on the property.
Many agriturismos are set in beautifully restored farmhouses surrounded by vineyards, olive groves, and rolling hills, offering a peaceful and authentic rural experience.
- Pedore Spedalone – This organic farm provides a wholesome experience with fresh food and a peaceful setting. Kids can enjoy the farm environment and learn about nature in a safe, rural space.
- La Bandita Townhouse (nearby in Pienza) – While more of a boutique hotel, it’s very family-friendly with spacious suites and easy access to outdoor activities in the Val d’Orcia countryside.
- Agriturismo Val di Tufo—This property offers an infinity pool and plenty of open space, making it ideal for families who want both comfort and fun for their children. The spacious and quiet property is excellent for kids to run around in.
Day 1: Pienza and an Authentic Dinner
Morning: Explore Pienza
Pienza’s location in the Val d’Orcia makes it a fantastic base or stop when exploring southern Tuscany. Its proximity to other charming towns means you can easily combine visits if you have more time. For example:
- Montepulciano (about 15 minutes away) is famous for its Vino Nobile wine and medieval architecture.
- Montalcino (around 30 minutes) for its fortress and the Brunello di Montalcino wine.
- Bagno Vignoni is unique for its thermal hot springs in the main square.
- Monticchiello offers stunning views and a peaceful, authentic Tuscan village experience.
After resting and lunchtime at the hotel, we explored Pienza. Here are some recommendations on what to do in Pienza if you only have a few hours to spare:
Stroll the Charming streets of Pienza
Walking through the little streets of Pienza feels like stepping back in time. The town is small and full of history, with stone paths and old buildings.
As you explore, you’ll find cute shops and cozy cafes. The main street, Corso il Rossellino, is great for a stroll and discovering local treats. It’s a peaceful and lovely place to enjoy real Tuscan life and take beautiful photos.
Visit the Cathedral ( Cathedral of Santa Maria Assunta)
Cathedral of Santa Maria Assunta is a wonderful experience that lets you enter centuries of history and art. This cathedral, found in several Italian towns like Pisa, Cremona, and Como, is renowned for its stunning Romanesque architecture, intricate façades, and beautiful interior frescoes and artworks.
Try Pecorino Cheese
Sample this famous local cheese, a must-try delicacy. Many stores in Pienza have cheese displays.
You should try Pecorino cheese in Pienza because it tastes like Tuscany’s rich culinary tradition. Made from the milk of local Sardinian sheep grazing on the unique herbs of the Val d’Orcia, Pecorino di Pienza boasts a distinct, rich flavor that reflects the region’s terroir.
Enjoy a quick Gelato or Coffee
Gelato and coffee are always good ideas when in Italy! Stop at one of Pienza’s gelaterias or cafes for a treat. There is a homemade Gelato shop that you could try.
Visit the Gladiator Movie Scene
If you love the movie Gladiator, you’ll enjoy visiting the spots near Pienza where some scenes were filmed.
Walking or driving along these paths allows you to enjoy amazing views of the rolling hills while imagining the movie scenes come to life. Read detailed directions here.
What to know before visiting the Gladiator movie scene:
- The famous cypress tree-lined road, often called the “Gladiator Road,” is easily accessible from Pienza and offers breathtaking views perfect for photos.
- You can start your walk or drive from Pienza and follow trails or roads that pass through the picturesque countryside where Ridley Scott filmed several scenes.
- Remember to wear comfortable shoes and bring water, especially in warmer months.
- Parking is near Pieve dei Santo Vito, which is close to some of the best viewpoints.
Afternoon: Hit the playground when visiting Pienza, Tuscany, with kids
We have not seen many or any playgrounds in Rome and Florence near the main attractions, but we were pleased to see one just a 4-minute walk from our hotel. It was small but enough for them to have a lot of fun.
Evening: Dinner at Locado Demetra
After strolling around lovely Pienza, we went to dine at Locanda Demetra in the nearby town of Montalcino.
We were very pleased when we arrived and saw many toys for the kids in the yard. It was an excellent idea for parents to enjoy a quality meal time and for kids to play in the yard. We had to take food for them outside as they did not want to stop playing.
In addition to the restaurant, Locanda Demetra includes a cooking school where you can learn to prepare traditional Tuscan dishes. It also offers rooms for overnight stays, making it a whole farm-stay experience.
The restaurant has a beautiful garden and serves dishes made from fresh, local ingredients, emphasizing sustainability and seasonality.
Our four—to five-course meals were outstanding, prepared by a fantastic chef. Every dish was filled with unique, well-balanced flavors. If you want a luxurious dining experience, this is the one.
Day 2: Hotel, Montichello, Cypress Tree Drive, Authentic Dinner
Morning Relaxation at the Hotel
Do not forget why you arrived in Tuscany in the first place and get lost in its serene surroundings. On our second morning, after a delicious breakfast at San Gregorio Hotel, we spent two hours by the pool before exploring Montelchino and finding the famous cypress tree drive.
Explore Montichiello’s Historic Center
Monticchiello is a picturesque medieval village between Pienza and Montepulciano in the Val d’Orcia region. It offers a peaceful and authentic Tuscan experience.
It is one of the least crowded and quietest little villages we visited—there are no big shopping opportunities if you want one. You will find calm, pretty cobblestone streets and pathways. While there are not many cars, always be careful with kids, and cars do pass by.
Wander through narrow cobblestone streets lined with stone houses, soaking in the medieval atmosphere.
Check out Teatro Povero (Summer Months)
This unique theater is a community-run open-air theater known for its original plays that reflect local life and history. It usually performs in summer, making it a great activity to attend with kids if you are around during the summer months.
Visit San Leonardo e Cristoforo Church.
If you visit Monticchiello, don’t miss the beautiful Church of Santi Leonardo e Cristoforo. It dates back to the 13th century and is perched at the village’s highest point.
The church’s Romanesque-Gothic façade is stunning, and inside, you’ll find impressive frescoes from the 14th and 15th centuries painted by artists from the Sienese school.
One of the highlights is an incredible altarpiece of the Madonna and Child by Pietro Lorenzetti, a famous artist from that era. It’s a fantastic spot to soak up some history and art while enjoying the charm of this Tuscan village.”
Enjoy Val d’Orcia Views
Experience some of the most breathtaking views in Tuscany, and Monticchiello is the perfect spot to take it all in. Perched like a terrace overlooking the Val d’Orcia, this charming village offers stunning panoramic vistas of rolling hills, vineyards, and cypress-lined roads that stretch as far as the eye can see.
Enjoy a Little Playground time
Monticchiello, a small medieval village, doesn’t have large modern playgrounds, but it offers a charming small playground area perfect for young children to enjoy outdoor play.
This cozy spot provides a safe and shaded environment where kids can run around and have fun while parents relax and enjoy the beautiful village surroundings.
The playground’s intimate setting complements Monticchiello’s peaceful, historic atmosphere, making it a nice little break for families exploring the village. Nearby regional towns offer larger facilities for more extensive playground options.
Find a Famous Cypress Tree Drive
If you’re exploring Tuscany, you can’t miss the iconic cypress tree drives that perfectly capture the region’s timeless beauty. These scenic roads lined with tall, slender cypress trees create picture-perfect moments and peaceful drives that are truly unforgettable.
Here are two of the most famous cypress tree drives near Monticchiello that you should hit:
Monticchiello to La Foce Cypress Drive
Start your drive from Monticchiello and head south on the SP146 toward Chianciano Terme. Then take the SP88 east, famous for its beautiful cypress-lined roads leading directly to the La Foce estate.
At La Foce, you can explore the magnificent Renaissance-Baroque gardens and enjoy the peaceful atmosphere of the estate. After your visit, you can return the same way or explore nearby villages like Sarteano or Castiglione d’Orcia for more Tuscan countryside charm.
We made a quick stop by the Palazzo Massaini near Pienza, just a short detour north of the SP146 road you’ll be taking between Monticchiello and La Foce. The entrance to the palace was so dreamy that we could not stop ourselves from taking pictures here.
2. Strada del Vino Nobile Drive with La Foce Detour
Begin your drive from Monticchiello heading east on SP146 toward Montepulciano, following the famous Strada del Vino Nobile through vineyards and rolling hills lined with cypress trees. Midway, detour south via SP88 to visit the La Foce estate. This detour adds a cultural highlight to your wine route, allowing you to enjoy La Foce’s stunning gardens and panoramic views before returning to the main wine road. Continue your journey through Montepulciano’s scenic vineyards and charming towns, making this an ideal blend of nature, culture, and wine tasting.
Dinner at Dopolavoro La Foce
Dopolavoro La Foce is a charming restaurant located in the scenic La Foce area near Pienza, Tuscany. It offers traditional Tuscan cuisine, focusing on seasonal dishes made from local ingredients, often enhanced by the estate’s extra-virgin olive oil.
The restaurant features a beautiful setting surrounded by greenery and stunning Tuscan panoramas, providing a relaxing and authentic dining atmosphere.
This place was our absolute favorite in Italy, with its food and atmosphere.
The menu includes handmade pastas like ravioli filled with roasted meat and pecorino cheese fondue, and classic Tuscan dishes like pici pasta with ragù. Guests appreciate the quality of food, attentive service, and welcoming ambiance. The restaurant also has outdoor seating, allowing diners to enjoy the picturesque landscape while eating.
Tuscan Cuisine
Sampling Tuscan cuisine in Pienza, Montepulciano, and Val d’Orcia offers a memorable blend of artisanal cheeses, rich local wines, and rustic classics. Fresh, regional ingredients shape meals, and distinctive flavors set each town apart.
Best Time to Visit Tuscany With Kids
The best time to visit Tuscany is from April to June and September to October. These months offer mild temperatures and fewer tourists than the busy summer period, making sightseeing in Pienza, Montepulciano, and Val d’Orcia more enjoyable.
During July and August, daytime temperatures often rise above 30°C (86°F), and popular spots become crowded. If traveling in summer, early mornings and late afternoons are best for outdoor activities.
Navigating Parking and Driving Rules
Travelers exploring Pienza, Montepulciano, and the Val d’Orcia should prioritize comfort. Breathable clothing is a must, as spring through early fall often brings warm days and cooler evenings.
A light jacket or sweater can help with the evening chill. Walking shoes with good grip are recommended; Tuscany’s cobblestone streets and hilly villages require sturdy footwear.
Booking Tips for the Best Experience
Start by deciding if you want a countryside experience or to stay in the heart of a historic town. Choose agriturismos for quiet evenings and homemade meals, or select a central hotel for easy walking to restaurants and wine bars.
Look for properties with strong reviews for cleanliness, hospitality, and views. Many visitors mention that staying near Pienza or Montepulciano allows for easy day trips to nearby sites, such as local cheese farms and vineyards featured in the travel guide.
Plan your trip around what matters most—proximity to towns, unique features like on-site wine tastings, or simply the most picturesque setting for a relaxing stay. Checking cancellation policies and breakfast options also makes the booking process smoother.
Summary: Tuscany Countryside with Kids
Visiting the Tuscany countryside with kids offers a magical blend of stunning landscapes, charming medieval villages, and family-friendly activities that create unforgettable memories for all ages.
From exploring historic towns like Monticchiello and enjoying peaceful walks along iconic cypress tree-lined roads to discovering beautiful estates like La Foce and tasting local flavors at family-welcoming restaurants, Tuscany is a perfect destination for families seeking adventure and relaxation.
With plenty of outdoor spaces, cultural experiences, and delicious food, a trip to the Tuscan countryside promises fun and enriching moments for kids and parents alike.
Are you planning to visit other places in Italy? You may like to check out these posts below:
