Our Favorite 5-Day Tuscany Itinerary (Perfect for Families)
Planning a family trip to Tuscany? After spending several months living in Tuscany with our three kids, we found that 5–7 days is the ideal amount of time. We recommend staying in the countryside near Florence or Chianti, renting a car, visiting San Gimignano and Siena, and leaving plenty of time to enjoy Agriturismos, wineries with playgrounds, and relaxed afternoons.
There's something magical about Tuscany. Maybe it's the hilltop villages that look like they've barely changed in hundreds of years. Or maybe it's simply the slower pace of life that makes you feel like you can finally breathe. When people plan Tuscany, they often try to pack too much into a few days. But after spending months living in Tuscany, we learned that the real magic isn't checking landmarks off a list—it's slowing down enough to actually enjoy them.
For this itinerary, I recommend staying at an Agriturismo just outside Florence and using it as your home base. During the day, you'll explore medieval villages, vineyards, and one of Italy's most beautiful cities. In the evenings, you'll come back for sunset swims, long dinners, and quiet nights in the countryside.
If you're traveling with kids, I honestly can't imagine a better way to experience Tuscany.
Why Stay at an Agriturismo?
If you've never heard of an Agriturismo before, think of it as one of Italy's best-kept travel secrets. Many are working farms that have been transformed into beautiful accommodations complete with pools, incredible restaurants, vineyards, olive groves, and plenty of space for kids to run around.
For families, they're the perfect mix of relaxation and adventure. Our kids loved being able to run around the big open green spaces, with swimming every afternoon, watching the farm animals, and having room to explore after a day of sightseeing.
Even better? Most are only 30–45 minutes from Florence, making them an ideal base for day trips. You can see our full list of: Where to Stay in Italy With Kids: Why Agriturismo’s Are Perfect for Families
Where To Stay
One of the most important decisions you will make for this trip, is where you choose to stay! As you know, we highly recommend an Agriturismo right outside of Florence. For families, I recommend choosing an Agriturismo within about 30–45 minutes of Florence so you can easily take day trips while still enjoying the peaceful countryside.
Some of our favorites include:
Fattoria di Maiano(pictured above)
You can find the full list with more details here: Where to stay in Italy With Kids: Why Agriturismo’s are Perfect for Families
And if you are not sold on staying outside the city, here are a few other rec’s in and around Florence.
iQ Firenze: Hotel central located but not in the extremely busy part of the city so it’s quieter. They have a rooftop pool that is suitable for kids and many room typed available for families. Up to 7 people.
Hotel Croce Di Malta: Great family style room setups in a central location in Florence near the train station
Firenze Suite: This hotel is centrally located and you can walk to all major sites or museums. These rooms have good family set ups and you really get the Italian feel.
Day 1: Arrive & Enjoy Your Agriturismo
Don't overplan your first day. One of the biggest mistakes people make is trying to immediately start sightseeing.
➡ Check into your Agriturismo
➡ Explore the property
➡ Let the kids swim
➡ Enjoy dinner overlooking the Tuscan countryside
This is your chance to settle in and have a relaxing day by the pool. Explore the grounds and see what activities or things they have to offer.
Day 2: Florence
Read our full guide to visiting Florence with kids.
Florence is family friendly, but we don’t think you need more than full day or two here. Florence is very walkable, which makes it easy to get around, You can ask to basically everything we mention here. Rather than trying to visit every museum, focus on experiences your kids will actually remember.
We highly recommend the Leonardo Interactive Museum. Normal museums are all about “don’t touch this or that.”. This place is made for kids to touch and do every activity. We spent at least 3 hours here and the kids absolutely loved it!!!
Here is how we would spend the perfect day with kids in Florence:
1️⃣ Leonardo Interactive Museum
2️⃣ Go to Piazza della Repubblica carousel
3️⃣ Walk around the Duomo
4️⃣ Stop for Gelato
5️⃣ Walk across the Ponte Vecchio
6️⃣ Go to Boboli Gardens
7️⃣ Visit a Wine Window
8️⃣ Have dinner
Day 3: San Gimignano
San Gimignano is a UNESCO World Heritage Site and is considered one of the best-preserved medieval towns in Europe. It is only a little over an hour train ride from Florence. Known as the "Medieval Manhattan," its famous stone towers make it feel like you've stepped into another century. This was the perfect small village for both kids and adults to enjoy. We loved how it is not crowded like Florence but has enough to do to keep you busy for a full day.
It’s best to try to get here early to find parking, plus the town does get busy with tour buses. You can read our full post on:The Best Way to Spend the Full Day in San Gimignano with Kids
Spend your day:
Exploring the narrow streets
Climbing the towers (if your kids are up for it)
Get gelato
Playing in the open green spaces
Shopping local artisan stores
Taking in the incredible views over the countryside
Day 4: Lucca
There are many small hillside villages you could go to for the day. If you are set on one, do that. If you don’t know then we would suggest Lucca!
Unlike many of Tuscany's hill towns, Lucca is completely enclosed by Renaissance walls, making it incredibly walkable—and one of the easiest cities to explore with kids. The slower pace, charming piazzas, and car-free historic center make it feel relaxed from the moment you arrive.
One of the best things to do is rent bikes or a family surrey and ride the top of Lucca's famous city walls. The tree-lined path circles the entire historic center and is one of the most unique ways to see the city. Our kids loved it!
After your ride, wander through the beautiful streets and stop in Piazza dell' Anfiteatro! A one-of-a-kind oval piazza built on the site of an ancient Roman amphitheater. It's the perfect place to grab lunch or enjoy a gelato while the kids stretch their legs.
Then, climb the Guinigi Tower, famous for the trees growing on its rooftop. The climb is worth it for the incredible views over Lucca's rooftops and the surrounding countryside.
The perfect day in Lucca, would look some thing like this:
🚲 Rent bikes and ride the historic city walls
🍦 Stop for gelato in Piazza dell'Anfiteatro
🌳 Climb Guinigi Tower to see the rooftop garden
⛪ Visit the beautiful Piazza San Michele and San Michele in Foro
🛍️ Browse the local shops and artisan boutiques
🍝 Enjoy one last long Tuscan lunch before heading back to your Agriturismo
Lucca is the kind of place that doesn't require a checklist. It's best experienced slowly—wandering quiet streets, discovering hidden corners, and soaking in the relaxed atmosphere that makes Tuscany so special. It's the perfect way to end five unforgettable days in Tuscany.
Day 5: Slow Day & Soak Up the Tuscan Countryside
After several days of exploring Florence and Tuscany's charming hill towns, spend your final day exactly the way Tuscany is meant to be enjoyed. Slow.
Spend the entire day at the Agriturismo. The kids swam in the pool for hours, explored the property, and ran through the open green spaces while we relaxed with a coffee and took in the incredible views of the Tuscan countryside.
If your Agriturismo offers activities like olive oil tastings, farm tours, or cooking classes, today is the perfect time to enjoy them. Otherwise, grab a book, order an Aperol Spritz by the pool, and simply enjoy having nowhere to be. That's the beauty of a Tuscany family vacation.
For dinner, go to Cucina Pietraforte for your final dinner. This is just a short 10-minute walk up the hill. They have traditional Tuscan dishes, beautiful countryside views, and the absolute BEST employees. It's the perfect place to celebrate an unforgettable trip.
Sometimes the best day of the trip is the one where you don't have a plan at all. And my kids favorite memories were just swimming at the pool and walking the property seeing all the animals.
Pro Tips
Rent a car! You'll want the flexibility to explore the countryside. There are some places you can get by train, and most of the big cities it is better to not have a car. For this specific trip, I would highly recommend a car. Some of the best parts of Tuscany, are only accessible by driving there. Book a rental car here.
Stay at least 4–5 nights.
Don't switch hotels every day. You only need one base, but pick 2 if you are dead set on staying in multiple places.
Plan only one major activity each day.
Build in plenty of pool time. The kids love it and it can be a good way to break up the day.
Enjoy long dinners and the slower pace of life. That is the real joy of Tuscany.
FAQ about visiting Tuscany w/ kids
Q: Is Florence a good base for exploring Tuscany?
A: Florence is an excellent starting point, but we actually recommend staying just outside the city at an agriturismo. You'll enjoy the peaceful countryside while still being close enough for easy day trips into Florence and nearby Tuscan towns.
Q: What is the best time to visit Tuscany with kids?
A: Late April through June and September through early October are our favorite times to visit Tuscany. The weather is warm but comfortable, the countryside is beautiful, and it's generally less crowded than the peak summer months.
Q: Do you need a rental car in Tuscany?
A: Yes. While Florence is easy to explore without a car, you'll want a rental car to reach the countryside, agriturismos, wineries, and many of Tuscany's smaller villages. Having your own car makes it much easier to explore at your own pace.
Q: Is Tuscany expensive for families?
A: Tuscany can fit a variety of budgets. I would say it is actually a very doable trip for someone with kids who doesn’t want to spend a lot. Staying at an agriturismo often provides excellent value because you'll have more space, access to a kitchen, and family-friendly amenities like pools. Many of Tuscany's best experiences like walking through historic villages, enjoying scenic drives, and exploring local markets are either free or very affordable.
Q: What should you pack for Tuscany?
A: Comfortable walking shoes are essential because you'll spend a lot of time exploring historic streets. We also recommend packing swimsuits if you're staying at an Agriturismo with a pool, lightweight clothing for warm afternoons, a light jacket for cooler evenings, reusable water bottles, and sunscreen. You can view our storefront with the travel essentials we recommend. We are definitely a less stuff more adventure type of family so you don’t need to buy much.
Q: Is Tuscany stroller friendly?
A: It depends on where you go. Florence and Lucca are relatively stroller-friendly, especially compared to many of Tuscany's hill towns. Places like San Gimignano have cobblestone streets and hills, so a lightweight travel stroller or baby carrier can make exploring much easier. If you have young kids and are walking around any city or town, take the stroller. You will be happy.
Q: Is Tuscany better than the Amalfi Coast for families?
A: Both destinations are incredible, but they offer very different experiences. If you're looking for dramatic coastal views and beaches, the Amalfi Coast is hard to beat. If you prefer a slower pace, rolling countryside, charming villages, and room for kids to run and play, Tuscany is better. I would personally choose Tuscany with kids because it is easier to get around and less travel to get there.
