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Our Fantastic Tuscany Family Holiday |A Week-Long Itinerary

Spoiler alert: we weren’t actually supposed to go on a Tuscany family holiday; we were supposed to bask in Africa’s sunshine during a week-long trip to Morocco.

But sometimes plans change, and we’ve learned over the years that you’ve gotta roll with those changes. Thankfully, spending one week in Tuscany for a family holiday is a pretty excellent backup plan.

Even in the winter, Italy can be fantastic. This family of five shares their last-minute family trip to Tuscany.

The bright side to not having much time to plan a Tuscany family holiday is that you don’t spend all your time and energy researching every last detail.

Thankfully, (not to toot my own horn, but…) this was a pretty fantastic week-long itinerary for Tuscany.

All The Fun Stuff We Did in Tuscany

Here’s a quick look at what we did in and around Italy during our week in Tuscany with kids:

🔍 Explored Pisa, Florence, Cinque Terre, and Volterra.

🥩 Dined at fancy restaurants (one planned-ish, one was not)⁠.
Trattoria Dall ‘Oste in Florence
Il Cavalier Restaurant at Castello di Gabbiano

🍷 Drank cheap, delicious table wine⁠

🍝 Took a pasta-making class⁠ at our Agriturismo

🍕 Ate lots of pizza and heaps of pasta⁠

🛵 Went to a Vespa museum!!!

🍷 Had a spur-of-the-moment wine tasting⁠ at Castello di Gabbiano.

🥾 Climbed the Leaning Tower⁠ in Pisa and the Duomo in Florence.

🍑 Saw David’s butt⁠

🍦 Enjoyed gelato every day⁠

🚂 Rode the train all over

🌊 Checked out Cinque Terre.

🪨 Glanced at where Carrera marble comes from⁠ on our train to Cinque Terre.

🚙💨 Drove through the windy Tuscan hills⁠

Find Even More to Do in Tuscany:

Quick Tips for Your Tuscan Family Holiday

  • Italians eat late compared to Americans. Most restaurants in smaller towns won’t even open until 7 pm, 7:30 pm, or even 8 pm. If you’re visiting Tuscany with kids, plan accordingly with a late lunch, making dinner in your agriturismo, or triple-checking that a place is open early. (Big cities, like Florence, will have more accessible restaurant times.)
  • Italy basically shuts down in the middle of the day for something called riposo, or “rest time.” Everything from shops, restaurants, and even gas stations will literally close down for a couple of hours every day. Does everything close? No, especially in very large cities, but the majority of places will shut down in small towns.
  • Speaking of things shutting down: Sundays are also big rest days for Italians; many things—including grocery stores and gas stations—may be closed on a Sunday.
  • You may have to pee in a hole. Yup, I said it. We didn’t encounter any on this trip, but you may be very surprised to go to a restroom and find a hole in the ground instead of a toilet.

Tuscany Family Holiday Week-Long Itinerary

Thankfully, my husband and I have both been to Tuscany on holiday before (about a decade earlier; before we had kids), so there wasn’t a lot of pressure to see everything and have to do it all.

This trip was relaxed and chill, which was nice to not have any expectations. And the nice thing is that we still did a lot of fun things around Tuscany with the kids.

Here’s our week-long itinerary for Tuscany with a slightly more detailed look at what we did each day:

Day One: The Leaning Tower of Pisa

We flew into Pisa (didn’t even stop to grab luggage since we just used our carry-on backpacks), grabbed our rental car, and drove straight to the Leaning Tower (we parked here).

After Pisa, we were going to check out another smaller town like Sienna or Lucca, too, but ended up cutting them for relaxing and taking it easy day instead of driving around more. Instead, we headed to our Agriturismo.

Day Two: Cinque Terre

Today’s destination: picturesque Cinque Terre!

We drove to Pisa and from there we took the train to La Spezia. At La Spezia, change to the Cinque Terre Express. We took that all the way to the northernmost town, Monterosso al Mare, working our way from the top down to the bottom.

Having been there twice before, in the summertime, I do not recommend going in the off-season. Almost every place was closed until the “tourist season began in late March/April. There was also construction everywhere. Plus, the Cinque Terre Express train doesn’t run as frequently.

Day Three: Florence

We spent the day in Florence, kicking things off with an excellent free walking tour that took us everywhere.

After the tour, we had lunch at Mercato Centrale, shopped at the outside leather market, went to the Leonardo di Vinci Museum*, and then capped off our day with a delicious dinner at Trattoria Dall ‘Oste.

Day Four: Wine Tasting and Volterra

Since we were there in the off-season and this was a quickly-planned trip, we went with something familiar and headed to Castello di Gabbiano for a delicious wine tasting. Thankfully, they also had a restaurant on site. However, if you’re visiting in peak season I recommend going for their casual eatery instead.

Fun fact: places in Tuscany don’t open until March for the season, so we were a bit early. Thankfully someone saw us and graciously gave us a wine tasting. It worked in their favor since we had several bottles shipped to us; we love their wine!

After lunch, we went to the sleepy town of Volterra to explore. Although we were there right during riposo, so nothing was open. It was still delightful to look around the quiet streets.

Day Five: Florence

We couldn’t get enough of Florence, so we went back for more! This time, we (okay, the kids and my husband) climbed the Duomo while I enjoyed a cappuccino on solid ground.

We had gelato, did more window shopping, and finished the day with another delicious meal.

We wish we climbed the Arnolfo Tower at Palazzo Vecchio (the views are supposed to be breathtaking), but it was sold out while we were there.

Day Six:

I like to think that we saved the best for last. We visited a Vespa museum near Pisa (in Pontedera). If you know me, you know this was a HUGE highlight! Plan on eating at this restaurant before/after you check out the Vespas.

After the museum, we went back to our Agriturismo for a pasta cooking class that I 100% highly recommend!

Day Seven:

Flew back home very early.

When we visited Tuscany

Our impromptu Tuscany family holiday was at the end of February 2023 with our three kids (ages 9, 8, and 6 years old at the time).

We had a short flight on RyanAir from Eindhoven, Netherlands, straight into Pisa, Italy, and then rented a car when we arrived.

Italy is wonderful any time of the year—you can never go wrong with visiting that gorgeous country. However, if I could pick any time to visit I’d probably skip the winter months.

The bright side to going on a family holiday in Tuscany during the winter months is that there are way fewer people! The streets were practically empty.

Our Family Friendly Tuscan Accommodations

I ended up booking pretty much the first place I found—Agriturismo Diacceroni—a great family-friendly Tuscany agriturismo in the heart of Italy, about an hour southeast of Pisa.

And that was that. Other families who’ve visited the area on a Tuscany family holiday recommended it, so I didn’t over-research and second-guess my decision, and it ended up being just what we needed.

We stayed in their two-bedroom apartment during our week in Tuscany but probably should have sprung for the three bedrooms just to have a little more room for our family.

My only complaint (okay, there are two of them) is that the pillows could’ve been better, and the wifi never connected well. I could’ve (should’ve) asked for more pillows, and the internet and lack of TV ended up being fine; we read books instead of watching TV at night.

Their pool was closed (big bummer), but that feature would be amazing if you’re in Tuscany with kids during the warm weather months.

Instead, my kids played at their ping-pong table and a little playground. They still had a great time.

They also have a restaurant, farm animals (you can ride horses), cooking classes, and other fun really fun experiences for families on holiday in Tuscany.

We said, multiple times, that we’d love to go back in late spring.

Other Great Places To Stay in Tuscany With a Family

While I don’t know if they have all the fun facilities like the place we stayed above, these are top-rated as some of the best places to stay in Tuscany with a family. If you’ve stayed in a place you recommend during your Tuscany family holiday, please let me know!

Overall Thoughts on Our Family Trip to Tuscany

Except not going to some of the other more popular towns like Lucca or Siena, we had a great time as a family in Tuscany.

I think one week in Tuscany is pretty perfect; it’s enough time to see popular places and also enjoy the surrounding area.

We ate all the food, drank all the wine, saw stunning sites, walked thousands of steps, and had a chance to relax and soak in the beauty around us.

I’m eager to share a full itinerary with all the details, so hopefully, that will come soon. In the meantime, feel free to comment and ask any questions about our trip!

Have you been on a family holiday to Tuscany yet?



  1. Hi~ your trip sounds amazing. So you stayed at the site for the week and then had a rental car. Did you walk the entire Cinque Terre? and then take the train back to your car and head home? I’m wondering how much we can do in one day.


    1. Hi! We did stay there the whole time as our “home base,” and we rented a car. We went to each stop in Cinque Terre, taking the train back and forth. Then we took the train at the end of the day back to the train station where we parked our car! Easy peasy 🙂

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