Explore Tuscany – San Gimignano and Siena

By our second day in Tuscany, it felt like the heatwave was personally stalking us across Italy. I opened the news that morning only to read: “San Gimignano, one of the worst-hit cities by today’s heatwave.” Perfect. Who in their right mind decides to go sightseeing there? Apparently me. But honestly—when you’re already in Tuscany, skipping San Gimignano would feel like skipping dessert. And I never skip dessert.

Originally, we had planned to rent a car in Florence because Tuscany really shines when explored on four wheels (bonus: you can yell “Stop!” every five minutes for photos). But plans changed when Hubby had to dash back to Jakarta for work, leaving us car-less. Thankfully, our lovely Airbnb host came to the rescue and introduced us to Alessandro, a private driver who would chauffeur us around for the day.

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

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

San Gimignano

San Gimignano, a small walled village about halfway between Florence and Siena, is famous for its fascinating medieval architecture and towers that rise above all the other buildings offering an impressive view of the city from the surrounding valley. At the height of its glory, San Gimignano’s patrician families had built around 72 tower-houses as symbols of their wealth and power. Although only 14 have survived, San Gimignano still retains its feudal atmosphere and appearance.

Alessandro dropped us in front of San Gimignano’s wall as cars were not allowed to enter within the city wall. We stopped for lunch first as Achita was awake and we were hungry. She asked for spaghetti and finished half portion, not bad!

After lunch we started strolling and tried to walk as much in the shade and took many stops to just enjoy the ambiance. We tasted their gelatos, drink a lot and slap more sunscreen.

Here’s what you can do in San Gimignano

Visit the Historic Center: San Gimignano’s historic center is a UNESCO World Heritage Site and is home to many well-preserved medieval buildings, churches, and towers.

Climb the Torre Grossa: The Torre Grossa is the tallest tower in San Gimignano and offers panoramic views of the town and the surrounding countryside.

Visit the Piazza della Cisterna: The Piazza della Cisterna is a charming square located in the heart of San Gimignano’s historic center. It’s surrounded by medieval buildings and is home to a beautiful well.

Explore the Duomo: The Duomo is San Gimignano’s main church and is known for its beautiful frescoes by Ghirlandaio and other Renaissance artists.

Sample the Local Wine: San Gimignano is located in the heart of Tuscany’s wine region and is known for its Vernaccia wine. You can sample the local wine at many of the town’s restaurants and wineries.

Visit the Museo Civico: The Museo Civico is located in the Palazzo Comunale and features many important works of art, including frescoes by the Renaissance painter, Memmo di Filippuccio.

Take a Cooking Class: San Gimignano is known for its delicious Tuscan cuisine, and you can learn how to make traditional dishes at a cooking class.

Walk along the Medieval Walls: San Gimignano’s medieval walls offer stunning views of the surrounding countryside and are a great way to explore the town’s history and architecture.

Siena

Siena is known for Italy’s loveliest medieval city and worth a a trip even if you are in Tuscany for just a few days. Siena’s heart is its central piazza known as Il Campo, known worldwide for the famous Palio run here, a horse race run around the piazza two times every summer. Movie audiences worldwide can see Siena and the Palio in the James Bond movie, Quantum of Solace.

Siena is said to have been founded by Senius, son of Remus, one of the two legendary founders of Rome thus Siena’s emblem is the she-wolf who suckled Remus and Romulus – you’ll find many statues throughout the city. The city sits over three hills with its heart the huge piazza del Campo, where the Roman forum used to be. Rebuilt during the rule of the Council of Nine, a quasi-democratic group from 1287 to 1355, the nine sections of the fan-like brick pavement of the piazza represent the council and symbolizes the Madonna’s cloak which shelters Siena.

The Campo is dominated by the red Palazzo Pubblico and its tower, Torre del Mangia. Along with the Duomo of Siena, the Palazzo Pubblico was also built during the same period of rule by the Council of Nine. The civic palace, built between 1297 and 1310, still houses the city’s municipal offices much like Palazzo Vecchio in Florence. Its internal courtyard has entrances to the Torre del Mangia and to the Civic Museum.

Siena is only 30 minutes drive from San Gimignano. Alessandro dropped us at the city wall because the car can not go in and told us to walk straight to Duomo which would be the center of Siena and start our sightseeing from there.

Here’s what you can do in Sienna

Tour the Duomo di Siena

The Duomo di Siena is a stunning Gothic cathedral that dates back to the 12th century. It’s known for its intricate facade, beautiful stained-glass windows, and intricate frescoes. As we walked to Duomo with Alyssa sleeping in her stroller I found out that the path to Duomo is ascending. I was about to have a mild heart attack after the last climb pushing a stroller. But the view from the top was breathtaking and I felt better right away.

Visit Piazza del Campo

Piazza del Campo is the main square in Siena and is one of the most iconic landmarks in the city. The square is surrounded by historic buildings and is home to the Palazzo Pubblico, which houses the Civic Museum.

Explore the Palazzo Pubblico

The Palazzo Pubblico is the town hall of Siena and is located in the Piazza del Campo. It’s home to several important works of art, including frescoes by Simone Martini and Ambrogio Lorenzetti.

Visit the Pinacoteca Nazionale di Siena

The Pinacoteca Nazionale di Siena is a museum located in the Palazzo Buonsignori. It’s home to an impressive collection of Renaissance paintings by Sienese artists such as Duccio, Simone Martini, and Ambrogio Lorenzetti.

Walk through the historic city center

Siena’s historic city center is a UNESCO World Heritage Site and is filled with narrow streets, historic buildings, and charming piazzas. It’s a great place to explore on foot and take in the city’s unique architecture and atmosphere.

See the Basilica of San Domenico

The Basilica of San Domenico is a Dominican church located in Siena’s historic city center. It’s known for its beautiful interior, which includes frescoes by Sienese artist Taddeo di Bartolo and a chapel decorated with the relics of Saint Catherine of Siena.

Take a Wine Tour

Siena is located in the heart of Tuscany’s wine region, and there are many wineries located just outside the city. You can take a wine tour and sample some of the region’s best wines while enjoying the beautiful countryside.

The heatwave was more bearable in Siena because it had many alleys who are shaded. Before going home we stopped by for more gelato from Nannini cafe as we walked back to the car.

We arrived home just in time for dinner. Rosalba, our host has prepared us dinner of homemade pasta with truffle cheese and strawberry dessert which OMG tasted so delicious.

If you ever needed a driver in Chianti I could recommend Alessandro who is based in Greve in Chianti. His car was very comfortable and he was also polite, friendly and drive well.