Towers, Towers Everywhere: A Heatwave Day Trip to San Gimignano and Siena

After our first few days settling into Panzano, I woke up on our second morning in Tuscany to a headline that felt personally aimed at me: “San Gimignano, one of the worst-hit cities by today’s heatwave.” Perfect. Who in their right mind goes sightseeing in that? Apparently, me. But honestly, when you’re already in Tuscany, skipping San Gimignano feels like skipping dessert. And I never skip dessert.

When Plans (Again) Change

We’d originally planned to rent a car in Florence — Tuscany really is best explored on four wheels, with the added bonus of yelling “stop!” every five minutes for photos. But those plans fell apart when Hubby had to dash back to Jakarta for work, leaving us car-less yet again. Thankfully, our Airbnb host came through and introduced us to Alessandro, a private driver who’d chauffeur us for the day.

Alessandro pulled up at 10am sharp, and before hitting the road we made an essential stop at the Coop supermarket. Snacks for Fabio and Achita: survival kit for parents. With crackers and juice boxes secured, we were officially road-trip ready.

And what a road it was. The drive from Panzano to San Gimignano is pure Tuscan magic — rolling Chianti hills, vineyards tumbling into valleys, olive groves shimmering in the sun. The kind of scenery that makes you want to break into opera, or at least record a dozen Instagram stories. The kids lasted exactly five minutes before falling asleep. Classic.

San Gimignano: The Town of Towers

San Gimignano is a small walled village about halfway between Florence and Siena, famous for medieval towers that rise above the rooftops and offer sweeping views over the surrounding valley. At the height of its glory, the town’s wealthiest families built around 72 tower-houses as symbols of status — only 14 survive today, but San Gimignano still wears its feudal atmosphere well.

Alessandro dropped us right outside the town wall, since cars aren’t allowed inside. We headed straight for lunch first, since Achita was awake and everyone was hungry. She ordered spaghetti and polished off half a portion — not bad for a heatwave appetite. Afterward, we strolled as much as we could in the shade, stopping often just to soak in the ambiance, taste the gelato, drink plenty of water, and reapply sunscreen more times than I’d like to admit.

Things to do in San Gimignano:

• Wander the historic center — a UNESCO World Heritage Site packed with well-preserved medieval buildings, churches, and towers.
• Climb the Torre Grossa — the tallest tower in town, with panoramic views over San Gimignano and the countryside.
• Sit at Piazza della Cisterna — a charming square at the heart of the old town, named for the well at its center.
• Explore the Duomo — San Gimignano’s main church, known for its Renaissance frescoes, including work by Ghirlandaio.
• Sample the Vernaccia — San Gimignano sits in the heart of its own wine region, and the local white is worth trying at any of the town’s restaurants or wineries.
• Visit the Museo Civico — housed in the Palazzo Comunale, with frescoes by Memmo di Filippuccio among its highlights.
• Take a cooking class — a good way to bring a bit of Tuscan cuisine home with you.
• Walk the medieval walls — for views over the countryside and a real sense of the town’s layered history.

How to get to San Gimignano from Florence (without a driver): There’s no direct bus or train, and no train station in town at all — the nearest is in Poggibonsi. The easiest combination is the bus from Florence’s Autostazione (next to Santa Maria Novella) to Poggibonsi, then a connecting local bus (line 130) into San Gimignano; door to door it’s roughly two hours. A train-plus-bus combination via Poggibonsi works too and takes a similar amount of time. If you’re coming from Panzano or elsewhere in Chianti as we were, there’s no useful public transport option at all — it’s a car, a private driver, or an organized tour, and the drive itself takes under an hour.

Siena: Italy’s Loveliest Medieval City

Siena is worth the trip even on a short Tuscany visit. Its heart is Il Campo, the famous shell-shaped piazza that hosts the Palio horse race twice each summer (movie buffs might recognize it from the James Bond film Quantum of Solace). Legend has it Siena was founded by Senius, son of Remus — hence the she-wolf emblem you’ll spot on statues throughout the city. The Campo itself sits where the old Roman forum once stood, rebuilt during the rule of the Council of Nine between 1287 and 1355, its fan-shaped brick paving said to symbolize the Madonna’s protective cloak.

Dominating the square is the red Palazzo Pubblico and its tower, the Torre del Mangia, built during that same period alongside the Duomo. Much like Palazzo Vecchio in Florence, it still houses the city’s municipal offices today.

Siena is only about half an hour from San Gimignano. Alessandro dropped us at the city wall — cars can’t enter here either — and pointed us straight toward the Duomo, the natural starting point for sightseeing.

Things to do in Siena:

• Tour the Duomo di Siena — a striking Gothic cathedral from the 12th century, known for its facade, stained glass, and frescoes. Fair warning: the walk up to it is a steady climb. I pushed Achita’s stroller the whole way and nearly had a minor cardiac event on the last stretch — but the view from the top made up for it almost immediately.
• Visit Piazza del Campo — Siena’s iconic main square, ringed by historic buildings including the Palazzo Pubblico.
• Explore the Palazzo Pubblico — the city’s town hall, home to important frescoes by Simone Martini and Ambrogio Lorenzetti.
• See the Pinacoteca Nazionale di Siena — a museum in the Palazzo Buonsignori with an excellent collection of Sienese Renaissance painting.
• Walk the historic center — another UNESCO World Heritage Site, all narrow streets and quiet piazzas.
• Visit the Basilica of San Domenico — a Dominican church known for its frescoes and a chapel holding the relics of Saint Catherine of Siena.
• Take a wine tour — Siena sits in wine country too, with several wineries a short drive from the city.

How to get to Siena from Florence (without a driver): This one’s genuinely easy — Siena is well served by both bus and train from Florence, each taking a little over an hour. The bus (Autolinee Toscane, from the Autostazione next to Santa Maria Novella, arriving at Piazza Gramsci) is generally the faster and cheaper option and drops you closer to the center; the train from Santa Maria Novella arrives at Siena’s station, which sits below the old town, so you’ll need a short bus ride, a taxi, or the escalators up to reach Il Campo. From San Gimignano, it’s a similar story to the Florence–San Gimignano leg: a local bus to Poggibonsi with a connection onward, or about 45 minutes by car.

Winding Down

The heatwave was far more bearable in Siena, thanks to its shaded alleys. Before heading home, we stopped for one more round of gelato at the historic Nannini café on the walk back to the car. We arrived home just in time for dinner — Rosalba had prepared homemade pasta with truffle cheese and a strawberry dessert that was, honestly, some of the best food of the whole trip.

Closing Thoughts and Practical Tips

Looking back, this was one of those days that could easily have gone sideways — heatwave, no rental car, two towns, two tired kids — and somehow turned into one of my favorite days in Tuscany. A few things I’d pass on if you’re planning something similar:

• Do both towns in one day only if you’re comfortable moving fast. San Gimignano and Siena together make for a full, slightly rushed day; if you’d rather linger, split them across two trips.
• A car (or a driver) is genuinely worth it for this route. Public transport between Chianti and either town is patchy at best, involving multiple transfers and several hours each way. If a rental car isn’t in the cards, a private driver is a comfortable and not unreasonably priced alternative.
• Beat the heat where you can. Aim for an early start, stick to shaded streets, and don’t underestimate how much water and sunscreen a Tuscan summer demands — heatwave or not.
• If you’re pushing a stroller, brace yourself for the Duomo climb in Siena. It’s worth every uphill step, but know what you’re signing up for.
• If you ever need a driver in Chianti, I can genuinely recommend Alessandro, based in Greve in Chianti. Comfortable car, polite, friendly, and a careful driver — exactly what you want on winding Tuscan roads with sleeping kids in the back.

Next up: more days under the Tuscan sun, and finally, Hubby rejoined our trip.