Tuscany: Montepulciano, San Gimignano and Siena

We couldn’t have asked for better travel buddies than my brother Neil and his wife Asia. Our “travel styles” (our balance of gluttony and exploring) are totally aligned, and the kids got quality uncle & auntie time!

We spent the first half of our Tuscan holiday based near Pienza. We also did a fun, kid-friendly pasta making class at Al Gelso Bianco. Tristan managed to sleep through the cooking portion and wake up in time to eat, and Auden had a blast making gnocchi and spaghetti!


Montepulciano is so much fun! First of all, look at this quirky clown tower. What’s the deal with that guy? I couldn’t believe he actually rang the bell on the hour.


Getting up the hilly roads to Montepulciano was no small effort. It nearly killed our poor Fiat Panda rental, but thankfully, we made it to a parking lot. This is a really hilly town, with lots of steps and inclines, so you’ll earn your wine if you’re carrying kids! Montepulciano has an amazing web of wine caves and Etruscan tombs below the town, so be sure to visit at least one (the visits are free).

The streets are lined with shops offering wine tastings, and we loved Cantina Fattoria della Tolosa. You can visit the cave under the shop, before the generous free tasting. The wine is great – we bought a few bottles – and the man behind the counter is funny and knowledgeable. There are wine tastings at every step, but we’re happy we did this one.

Next up was quite the spread at La Vineria di Montepulciano. They don’t offer typical Tuscan restaurant fare (pasta, pasta, pasta), but we were ready for something a little different and these pretty platters hit the spot! They don’t have high chairs, changing tables or a kids menu, but children are welcome. My kids were totally happy to eat cheese, bread and prosciutto!

I love all these little hilltop towns in Tuscany, with their ancient stone walls, cobbled streets and charm. Montalcino, Pienza, Montepulciano and San Gimignano are quite different from each other, so try to make your way around them.

San Gimignano

The medieval town of San Gimignano is known for its iconic towers, which create a dramatic skyline against the rolling hills.


This town is best for a day trip. There are a few options for lodging, but the price to quality ratio is much worse than you’ll find elsewhere. We stayed just outside the walls, and would recommend doing a day trip from Podere Spedalone, Siena or Florence.


Breakfast in the valley under San Gimignano

As soon as you enter the massive gate, you are transported back several centuries. More so than in Montepulciano, Montalcino or Pienza, I really felt like I could imagine what life was like in the medieval heyday of San Gimignano.

Wander through the streets and alleys, admire the well-preserved towers and check out the panoramic views along the outer walls.

Right in the central piazza, you’ll see people lined up for Gelateria Dondoli. It’s open late, so you can go back a few times… no need to stress about how many flavours there are to choose from. Or you can get 4 cones at once, I’m not here to judge.

Weirdly, there seemed to be a lot of torture museums. I guess that’s part of the whole medieval vibe… We didn’t go in, but we may have told Auden that the skeleton hanging in a cage was mean to its little brother.


At this point in our holiday, Siena felt like a bustling metropolis. We parked in the free parking lot near Fortezza Medicea and left our cars there for a couple of days. Your best bet is to get there early in the morning, when a few spots open up. All the towns I’ve highlighted so far have ZTL/traffic restrictions, and you get a massive fine if you drive into them. (Here’s the parking guide I used to plan ahead for parking and avoiding the ZTL.)


Piazza del Campo is Siena’s defining characteristic, and it’s always crowded with people sitting on the ground and the surrounding cafes, people-watching and chatting. Unless you’re as (un)lucky as me, in which case your baby wakes you up at the crack of dawn and you have it all to yourself.


When your alarm clock is a 1 year old, you get to see the piazza before the crowds

Siena is second only to Florence for its wealth of architecture and art museums, and the cathedral is breathtaking. To be honest, Neil and Asia indulged in the cultural wealth while Matt and I did more toddler-friendly activities. But there are so many resources on Siena for adults, so I’ll just cover Siena for young families.

The Siena Natural History Museum at the Accademia dei Fisiocritici was a huge hit. It’s on the outskirts of town, just outside of the wall, an easy walk from anywhere in Siena. There is a truly crazy collection of taxidermied animals, which fascinated the kids. Also, it’s free, so it’s okay if you can’t stay long.

Across the street from the Natural History Museum, we found the holy grail: a playground with a view. Kids need playground time — I have seen the playgrounds of every country we’ve been to — and it helps when it’s a scenic interlude.


Nearby, you’ll find the best pizza in town and the best gelato in Tuscany. La Piccola Ciaccineria serves up truly excellent, cheap, fresh and quick pizza by the slice, or you can order a pie. They have no sitting room – you just grab your pizza and sit on the steps across the street. La Vecchia Latteria was hands-down the best gelato we had on the entire trip, which is saying a lot, because we obviously prioritise our treats.

As long as we’re on superlatives, I’ll vouch for La Taverna di San Giuseppe, which was the best meal of an incredibly delicious trip filled with memorable meals. This is not a drill, people. They have two seatings and they’re always fully booked, so make a reservation for the 19:30 and (as always) request your high chairs. They are kid-friendly; the service and setting are lovely; the wine list is extensive; the food is excellent; and it’s reasonably priced.

After dinner, the stroll home is beautiful. Siena has done a beautiful job of setting the stage, with fancy sconces and uplighting.

We stayed in an apartment from Booking.com with 3 bedrooms, which worked out well for our group. It was nice to get some laundry done, the kids had a separate bedroom, and it was huge. The location was also perfect for us, as the parking was an easy walk and we could cross town to our gelato in 20 minutes. Note: although there is an elevator, it’s not actually step-free.

Next Up: Florence… and a surprise local twist


My heart in San Gimignano

3 thoughts on “Tuscany: Montepulciano, San Gimignano and Siena

  1. Asia says:

    This was the best walk down memory lane! Although now I’m REALLY craving that gelato in Siena… When can we plan the next adventure in gluttony? 🙂

    Liked by 1 person

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