When I hear people talk about visiting Tuscany, their itinerary reaches from the coast to the mountains. But the sunrise to sunset touring was not our plan. We wanted to have adventures while also saving time to eat relaxing meals on the terrace at sunset.  The time we spent sitting while our children made things in the gravel was an important part of loving our whole trip to Europe. The list below will give you an idea of what we made happen in between swimming and watching Italian cartoons.

 

STAY

Il Castagno (Apartment Caccia) in Il Castagno:  An agriturismo located between Volterra and San Gimignano. Our first floor apartment was shady, cool, and huge. The private terrace faced east and had expansive views (including the shared pool). Trees surrounding the terrace made it feel more secluded. There are two pools for all the apartments to share. The deep pool is connected to the shallow, children’s pool by a short river filled with pebbles and ending in a waterfall. This was ideal for relaxing with our preschoolers. There are a few short hikes, ducks and deer to feed, as well as a playing field with playground equipment. The roads up to the entrance are paved, making easy to get to and from for adventures.

 

PLAY

Montaione Playground: We frequented this town for the grocery stores (Coop & PAM). But the playground at the top of the hill is worth a stop. There is a slide, swing, and shade perched in front of the quintessential Tuscan view. That’s about all you need to catch your breath and remember that taking toddlers on vacation is worth it!

Collezione Gori Fattoria di Celle near Pistoria: A private collection of over 70 site-specific artworks on a 74 acre park-like land with buildings that go back to the 17th century. There is no admission fee, but you can only visit by guided tour. The tour we chose was a four hour hike. There are water fountains along the route and a toilet/restroom at the beginning.

Ponte Sospesso near Pistoria: Hike the longest pedestrian bridge in the world. We skipped this because they were asleep in the car when we drove by. We had just finished a four hour hike at a sculpture park, and we were all tired.

Castello di Ama in Chianti: A winery and restaurant with a few suites located in a small, charming hamlet. So small that there are only a handful (literally) of people who live there year round. The couple who runs the winery has commissioned site-specific artworks by contemporary artists that dot their property. The tour of the vineyard includes a tour of the artwork. It is a noteworthy collection that opens up the way you perceive both the place and the art.

Galleria Continua in San Gimignano: A large gallery and quiet space that is centrally located in the city or at least very close to the best gelato. Occupying a former cinema, the architecture of their spaces is worth the visit. They are also located in Beijing, France, and Cuba and represent a long list of artists, including a well known names like Buren, Hatoum, Guo-Qiang, and Kapoor.

Monteriggioni: This is the Tuscan hill town that preschoolers love! You can see it’s impressive circular wall from the highway. We arrived at the end of the day, just before dinner and parked in the parking lot right beside the gate. Follow the road up the hill and pass the parking lot at the bottom of the hill to find another lot with easier access. The town walls and towers are almost entirely intact, and the town is very small. So children can easily grasp the feeling of a walled village. There are two main attractions. First, there is a staircase and walkway that enables you to walk along the top of the outer walls. Second, there is an Armor museum, where you can try on the knights’ equipment. The museum is small and requires a fee, but it was a highlight! We didn’t stay in the town long, but it was a good place for our littles to make memories.

Volterra: A walled, hill town that is manageable for a half day. The city has fewer tourists than San Gimignano or Siena, which made parking easier. The city is not too big, enabling our preschoolers to enjoy touring. We arrived a little before dinner to explore the arches and alleys. And easily found dining options near Via Giacomo Matteotti.

San Gimignano: A popular hill town in Tuscany with a few excellent contemporary art stops, including public art and Galleria Continua. Explore the city by turning away from the crowds or stores and search for the quiet streets. There are multiple parking lots outside the city walls. Signs tell you how many parking spots are available in each lot. More information is available here. Note that P1 lot requires a hike up the hill or for you to wait for the  park-and-ride bus.

Siena: We visited Siena on a practice day for the Palio. It was as crazy as you can read about, but not as crazy as I thought it would be. At the last minute, we purchased seat space in the balcony of someone’s house who had a view of the piazza del Campo. Watching the crowds is as fun as watching the (very short) horse race. Our visit was dominated by the Palio, but I found the mapitout-siena.com guide helpful for locating playgrounds.

 

EAT

Gelateria Dondoli in San Gimignano:  THE BEST GELATO. All I can say is that we stopped for gelato all over Italy and there is a quality difference. This one is good, so good. Worth the line, a double scoop, and a second visit.

Next visit, we are not going to miss these two gems that I found out about too late. If you go, let us know about feasting with Dario Cecchini near Greve in Chianti or Saturday night dinner at Fattoria Poggio Alloro near San Gimignano.

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