Family Adventure in the Medieval Town of San Gimignano

First Impressions of San Gimignano: A Step Back in Time

After months of planning, our family adventure in San Gimignano has finally begun! Leaving Toronto behind, we landed in Florence and drove through the rolling Tuscan hills to this medieval town. The anticipation was high, especially for Zayn, who's been studying castles and knights in school. San Gimignano, with its towering skyline, promised to be a living history book, and I couldn't wait to dive in. Aisha, ever the culture enthusiast, was eager to soak in the Tuscan atmosphere, while I was looking forward to capturing it all through my lens.

Our first day was packed with exploration, starting with the ancient gates and winding through the heart of the town. The summer air was warm, but a gentle breeze kept it comfortable as we wandered. It's July, and the town is bustling with tourists, but the atmosphere is festive and inviting. I am so glad we finally made it here!

Stepping Through History at Porta delle Fonti

Our exploration began at Porta delle Fonti, one of the ancient gates that once guarded the entrance to the village. As we approached, the impressive stonework and intricate details of the gate immediately transported us back in time. I could almost hear the echoes of medieval footsteps and the clip-clop of horses' hooves. Zayn was particularly fascinated, peppering me with questions about who built it and how old it was. I tried my best to answer, feeling like a tour guide in my own right. I explained to him that Porta delle Fonti also provided access to the medieval public springs located just outside the walls.


Explore Porta delle Fonti, a historical gateway in San Gimignano, a perfect blend of medieval charm and stunning Tuscan landscapes.
We walked through the gate and down the short, steep descent of Via delle Fonti. The ancient spring is made from ten stone arches that open onto the basins. Six of the arches reflect the Romanesque style of the 13th century, while four showcase Gothic architecture from the 14th century. I could picture women doing their laundry in the washing troughs and children filling bottles with fresh water.

The Heart of San Gimignano: Piazza del Duomo

Next, we made our way to Piazza del Duomo, the heart of San Gimignano. This square has been the center of the town's religious and political life since the Middle Ages. The Collegiata, or Duomo, dominates the square with its stunning Romanesque architecture. I explained to Zayn that the piazza marks the intersection between the Via Francigena and the old Pisa-Siena Road. Aisha pointed out the various buildings surrounding the square, including the Palazzo Vecchio del Podestà and the Torre Rognosa. The trapezoidal shape of the piazza, with its brick pavement, added to its medieval charm.


Discover the enchanting Piazza del Duomo, a medieval square in San Gimignano, where history, art, and stunning landscapes converge in Tuscany.

San Gimignano is more than just a destination; it's an experience that immerses you in the heart of medieval Tuscany.

Zayn was particularly intrigued by the towers. I told him that San Gimignano was once known as the City of 72 Towers, built by noble families to show off their wealth and power. Today, only 14 remain, but they still create an impressive skyline. As we stood in the piazza, I tried to imagine what it must have been like during the town's heyday, with knights, merchants, and bustling crowds filling the square. I made sure to get a picture of Aisha and Zayn with the Duomo in the background, a perfect snapshot of our first day.

Reaching for the Sky: Torre dei Cugnanesi

Our final stop for the day was Torre dei Cugnanesi, one of the oldest and tallest towers in San Gimignano. Located in a charming little square between Via San Giovanni and Via del Quercecchio, it dates back to the 13th century. I told Zayn that the tower and the adjacent Palazzo dei Cugnanesi were part of the defensive system connected to the Arco dei Becci. The tower was owned by the Cugnanesi family, who were Ghibellines. It is unique because it was built outside the first city walls.


Explore the historic Torre dei Cugnanesi in San Gimignano, a majestic tower offering breathtaking views and a glimpse into Tuscany's medieval past.
As we stood beneath the tower, I pointed out the series of corbels supporting the balcony on the palazzo's façade. On the back of the building, we saw a bastion that was part of the original city wall. Zayn was amazed by how tall the tower was, and I could see his imagination running wild as he pictured knights defending the city from its heights.

A Taste of Tuscany: Culinary Delights

Of course, no trip to Italy is complete without indulging in the local cuisine. For breakfast, we enjoyed a delightful meal at Ristorante Bel Soggiorno, located in our hotel. The restaurant has been serving authentic Tuscan cuisine for five generations. The service was excellent, and the atmosphere was lovely. I had a cappuccino and a pastry, while Aisha opted for a fruit plate. Zayn devoured a stack of pancakes. It was the perfect way to start our day.


Experience authentic Tuscan cuisine at Ristorante Bel Soggiorno in San Gimignano - where every dish tells a story.
For lunch, we ventured to Osteria Delle Catene, a charming spot known for its traditional Tuscan dishes. The osteria has a great location and a beautiful view. I decided to try their truffle pasta, while Aisha chose the ribollita, a hearty Tuscan bread soup. Zayn, of course, went for the pasta with tomato sauce. The food was delicious, and the service was friendly and attentive. I was glad we chose a place that served traditional Tuscan dishes.


Experience authentic Tuscan flavors at Osteria Delle Catene in San Gimignano, where tradition meets culinary excellence.
As evening approached, we decided to treat ourselves to a special dinner at Cum Quibus - Ristorante Toscano. This restaurant is known for its exquisite Tuscan cuisine and refined ambiance. The staff was patient, and the service was fast. I ordered the Florentine steak, while Aisha chose the osso buco. Zayn enjoyed a simple pasta dish. The prices were reasonable, and the decor was nice. The food was delicious, and the atmosphere was perfect for a family dinner. I savored every bite of the steak, knowing that this was a meal we would remember for years to come. The wine list was also impressive, and I chose a local Chianti to complement our meal.


Experience exquisite Italian cuisine at Cum Quibus in San Gimignano, where tradition meets innovation in every delectable dish.

Sweet Treats and Tuscan Treasures

During our explorations, we couldn't resist stopping by the Truffle Boutique. The aroma of truffles wafted through the air as we stepped inside. The boutique offered a variety of truffle-based products, from truffle oils to gourmet snacks. I purchased a small bottle of truffle oil to bring back home, hoping to recreate some of the flavors we had enjoyed in San Gimignano. Aisha bought some truffle-infused pasta sauce. Zayn, surprisingly, was fascinated by the truffles themselves, asking about where they came from and how they were found.


Discover the essence of Tuscan cuisine at Truffle Boutique in San Gimignano, where exquisite truffle products await every food lover.
To cap off our evening, we stopped by Divinorum Wine Bar for a relaxing drink. The wine bar has a gorgeous panoramic view from inside the walled city. The staff was cute and friendly, and the service was professional. I ordered a glass of prosecco, while Aisha chose a Spritz. Zayn had a lemonade. As we sipped our drinks, we enjoyed the cool atmosphere and reflected on our first day in San Gimignano. I made sure to take a few photos of the stunning view, capturing the essence of this charming town.


Experience the finest wines and authentic Tuscan flavors at Divinorum Wine Bar in San Gimignano, where every sip tells a story.

Tomorrow's Adventure

As the sun set over San Gimignano, we made our way back to Hotel Bel Soggiorno, tired but content. Our first day had been a whirlwind of history, culture, and culinary delights. Tomorrow, we plan to visit SanGimignano1300, a museum that recreates the town as it was in the 14th century. We also intend to visit Galleria Continua, a contemporary art gallery, and walk along the Mura della Città, the city walls. For dinner, we've made reservations at Perucà, known for its traditional Tuscan cuisine. I'm excited to see what tomorrow brings, but for now, I'm grateful for the memories we made today. I am also happy that we did not forget any of the trip essentials, such as sunscreen, camera, travel guidebook, comfortable walking shoes, snacks for Zayn and travel adapters.


Discover the charm of San Gimignano at Hotel Bel Soggiorno, a cozy 3-star haven with modern amenities, perfect for exploring the city's historical beauty.

Final Thoughts

San Gimignano had exceeded all my expectations. It was a town that effortlessly blended history, culture, and natural beauty. As we drifted off to sleep, I couldn't help but feel grateful for the opportunity to share this experience with my family. I knew that the next few days would be filled with even more adventures, and I couldn't wait to see what San Gimignano had in store for us.

The events that are taking place in San Gimignano this July include the Nottilucente event, baroque music concerts, and opera in the Rocca. There are also Baroque Courtyard Concerts taking place in July.