A Family Adventure in San Gimignano's Timeless Charm

Stepping Back in Time: A Day of Discovery in San Gimignano

Today was a day of wandering through history, art, and the simple pleasures of Tuscan life. San Gimignano, with its medieval towers and winding streets, has a way of making you feel like you’ve stepped back in time. Ana, Luka, and I embraced the day, eager to explore every corner of this charming town.

Our morning began, as most do on vacation, with a delightful breakfast. We headed to Giardino Bistrot, a local favorite, drawn in by the promise of a peaceful start to the day. It was a perfect choice. The aroma of freshly baked pastries and strong Italian coffee filled the air. Luka, of course, went straight for the chocolate croissant, while Ana and I opted for something a bit lighter – fresh fruit and yogurt. The setting was lovely, with a view of the Tuscan hills just beginning to awaken. It's amazing how a good breakfast can set the tone for a day of exploration.


Experience exquisite Tuscan flavors at Giardino Bistrot in San Gimignano – where every dish tells a story.

Exploring Porta San Giovanni

After breakfast, we set out to explore Porta San Giovanni, the town’s most beautiful and impressive gate. Completed in 1262, its architecture immediately transported us back to the medieval era. As we walked through the archway, I imagined the countless travelers who had passed through this gate over the centuries. Luka was fascinated by the sheer size of the stones and kept asking how old it all was. It’s moments like these, sharing the wonder of history with him, that make these family trips so special. The gate opens onto Piazzale dei Martiri di Montemaggio, where the Convent of Saint Francis formerly stood.


Discover the charm of Porta San Giovanni, a historic gateway in San Gimignano, Italy, leading to breathtaking views and medieval wonders.

The beauty of San Gimignano lies not just in its stones and towers, but in the way it makes you feel connected to the past.

Climbing the Torre dei Cugnanesi

Next on our list was the Torre dei Cugnanesi, one of San Gimignano’s tallest towers. As we approached, its imposing structure stood out against the skyline, a testament to the town’s rich history. Dating back to the 13th century, the tower is closely associated with the Cugnanesi Palace and was part of the defensive system connected to the Arc of Becci. The tower is located between Via San Giovanni and Via del Quercecchio.


Explore the historic Torre dei Cugnanesi in San Gimignano, a majestic tower offering breathtaking views and a glimpse into Tuscany's medieval past.

Luka was excited about the climb, and Ana, despite her slight fear of heights, was game. The climb was a bit strenuous, but the views from the top were well worth it. From up high, we could see the entire town spread out before us, a sea of terracotta roofs and ancient stone. I tried to capture the panorama with my camera, but some views are simply too grand to be contained in a photograph. I made a mental note to buy an extra memory card; I wouldn’t want to run out of space during the rest of our trip. It was a mistake I had made before, and you'd think I would learn.

A Culinary Interlude at Osteria Enoteca I Quattro Gatti

By lunchtime, we were all quite hungry. We chose Osteria Enoteca I Quattro Gatti, a charming restaurant known for its authentic Tuscan cuisine. The atmosphere was cozy and inviting, and the menu was filled with local specialties. Ana and I decided to share a plate of pici pasta with ragu, while Luka opted for a simple but delicious margherita pizza. The food was exceptional, and the house wine was the perfect complement to our meal. I made sure to try some local Pecorino cheese as well. It reminded me of some cheeses back home in Slovenia. It's always a pleasure to discover new flavors and appreciate the culinary traditions of a place.


Discover authentic Tuscan flavors at Osteria Enoteca I Quattro Gatti in San Gimignano – where tradition meets culinary excellence.

Art and Culture at Galleria d’Arte Moderna e Contemporanea Raffaele De Grada

After lunch, we immersed ourselves in art at the Galleria d’Arte Moderna e Contemporanea Raffaele De Grada. Housed in the ancient monastery of Santa Chiara, the gallery is named after the Milanese painter who made San Gimignano his home. The collection includes works by De Grada, as well as other Tuscan artists from the 19th and 20th centuries.


Discover the vibrant world of modern art at Galleria d'Arte Moderna e Contemporanea Raffaele De Grada in San Gimignano, a unique cultural gem.

I was particularly drawn to the paintings of Niccolò Cannicci, whose landscapes captured the essence of the Tuscan countryside. Ana, with her architect's eye, appreciated the way the gallery space blended the old with the new. Luka, surprisingly, was quite engaged, pointing out his favorite colors and shapes in each painting. It’s wonderful to see him developing an appreciation for art and culture. The gallery is located inside the ancient monastery of Santa Chiara.

Shopping for Treasures at Macallè

No trip to Italy is complete without a bit of shopping, so we made our way to Macallè, a local shop known for its handmade jewelry. As Ana browsed the intricate designs, I admired the craftsmanship and attention to detail. Luka, ever practical, was more interested in finding a souvenir for his best friend back in Zurich. We eventually settled on a small, hand-painted wooden toy, which I’m sure he’ll love.


Explore Macallè, a charming jewelry store in San Gimignano, where stunning handcrafted pieces await every discerning traveler.

I ended up buying Ana a beautiful silver necklace with a delicate pendant. It was a small token of my appreciation for her unwavering support and adventurous spirit. As we left the shop, hand in hand, I felt a sense of contentment wash over me. It’s moments like these, sharing simple joys with the ones you love, that make life truly meaningful.

Dinner at Trattoria Antica Macelleria

For dinner, we chose Trattoria Antica Macelleria, a restaurant renowned for its traditional Tuscan cuisine and warm atmosphere. The reviews I had read online were promising, and we were eager to experience it for ourselves. The trattoria is known for its great service and friendly staff. As we stepped inside, we were greeted by the inviting aroma of grilled meats and simmering sauces. The restaurant was cozy and full of character. The decor created a calm and relaxed atmosphere.


Experience authentic Tuscan cuisine at Trattoria Antica Macelleria in San Gimignano - where tradition meets flavor in every dish.

We started with a selection of local cheeses and cured meats, followed by a hearty bowl of ribollita, a traditional Tuscan bread and vegetable soup. For our main courses, Ana and I shared a Florentine steak, cooked to perfection, while Luka devoured a plate of homemade ravioli. The food was simply divine, and the service was impeccable. The prices were reasonable.

As we savored our meal, we reflected on the day’s adventures. We had explored ancient gates, climbed medieval towers, admired beautiful art, and indulged in delicious food. San Gimignano had truly captured our hearts, and we were grateful for the opportunity to experience its magic together. The portions were generous and carefully prepared. The owner took personal care of the customers, adding a personal touch to the dining experience.

Looking Ahead

Tomorrow, we plan to visit the Chiesa di Sant'Agostino, Palazzo Comunale, Pinacoteca, Torre Grossa, and Fonti Medievali. I'm particularly excited about seeing the Palazzo Comunale and Torre Grossa, as I've heard the views from the tower are incredible. We might even stop by Bar Le Torri for a drink.

As I sit here now, writing in my journal, I can’t help but feel a sense of gratitude for this incredible journey. Sharing these experiences with my family is something I will always cherish. San Gimignano has given us memories that will last a lifetime, and I can’t wait to see what tomorrow brings.

“Traveling – it leaves you speechless, then turns you into a storyteller.” – Ibn Battuta