Exploring the Medieval Charm of San Gimignano with Family

A Day Among Towers & Treasures

Today, San Gimignano truly captured my imagination! From scaling its tallest tower to wandering through ancient churches, every moment felt like stepping back into the Middle Ages. It’s a place where history isn't just read; it’s experienced.

Our day began with a delightful breakfast at Chiribiri. This charming little spot, tucked away near Porta San Giovanni, offered a taste of genuine Tuscan hospitality. The owner was incredibly welcoming, and the simple, fresh pastries were the perfect way to start our explorations. Oliver, of course, was more interested in the pigeons strutting about the Piazza della Madonna than his *cornetto*, but a bit of coaxing (and a few strategically placed crumbs) got him happily munching away.


Discover authentic Tuscan cuisine at Chiribiri in San Gimignano - where tradition meets flavor in a charming setting.

Fueled up, we made our way to the Palazzo Comunale, Pinacoteca, and Torre Grossa. This trio of attractions is an absolute must for anyone visiting San Gimignano. The Palazzo Comunale itself is a stunning example of medieval architecture, its sturdy walls echoing with centuries of civic duty. Inside, the Pinacoteca, or art gallery, was a treasure trove of Sienese and Florentine masterpieces. I found myself particularly drawn to the frescoes in the Sala di Dante, depicting knightly tournaments and hunting scenes. It’s incredible to think that these vibrant images were created way back in the 13th century!


Discover the timeless beauty of San Gimignano's Palazzo Comunale, featuring exquisite art collections and stunning views from Torre Grossa.

Art is not what you see, but what you make others see.

Of course, the highlight here was climbing the Torre Grossa. At 54 meters, it’s the tallest of San Gimignano’s famous towers, and the views from the top are simply breathtaking. The climb itself is fairly straightforward, with wide metal stairs making it easier than some of the tighter spiral staircases we’ve encountered in other towers. Even Oliver managed most of it himself, though I did have to hoist him up the final ladder to the very top. The panorama of the Tuscan countryside, with its rolling hills, vineyards, and olive groves, was worth every step. I could have stayed up there for hours, soaking it all in.

After descending from the Torre Grossa, we took a moment to appreciate the Palazzo's courtyard, admiring the coats of arms and the old water well. It’s amazing how much history is packed into every corner of this town. Emily, ever the pragmatist, was more interested in finding a gelato shop, but even she had to admit that the Palazzo Comunale was pretty impressive.

Next on our list was the Chiesa di Sant'Agostino. This church, located in Piazza Sant'Agostino, is a bit more off the beaten path than the Duomo, but it’s well worth a visit. The exterior is simple and austere, built entirely of brick in a Romanesque-Gothic style. But inside, it’s a different story. The church is home to a stunning collection of frescoes, most notably the cycle depicting the Life of Saint Augustine by Benozzo Gozzoli. These frescoes, painted in the 15th century, are considered some of the best-preserved examples of Tuscan Renaissance art. I was particularly struck by the vibrant colors and the detailed storytelling in each scene. It’s easy to get lost in the narratives, imagining what life was like in San Gimignano during the Renaissance.


Discover the captivating beauty and rich history of Chiesa di Sant'Agostino, a must-visit Catholic church in the heart of San Gimignano.

After the visual feast of Sant'Agostino, we decided to take a stroll to find the Bagolaro di San Gimignano - Albero monumentale. This monumental hackberry tree, located near the archaeological museum, is a true testament to nature's resilience. Estimated to be around 150 years old, it stands tall with a wide, spreading canopy. It’s quite a sight to see such a grand old tree in the heart of a medieval town. Oliver was fascinated by its gnarled branches and the way the sunlight filtered through its leaves. We spent a few minutes just sitting in its shade, enjoying the peace and quiet away from the bustling crowds.


Experience the grandeur of the Bagolaro di San Gimignano, an ancient tree and a natural monument in the heart of Tuscany's medieval gem.

For lunch, we headed to Ristorante La Stella. This restaurant, with its ancient origins dating back to the 1200s, offered a warm and welcoming atmosphere. We savored traditional Tuscan dishes like handmade pappardelle and succulent steaks. Emily enjoyed a glass of house wine, while Oliver devoured his pasta with gusto. It was a perfect midday break, recharging us for the afternoon's adventures.


Experience authentic Tuscan cuisine at Ristorante La Stella in San Gimignano, where delicious food meets warm hospitality in a picturesque setting.

With renewed energy, we ventured into Le Torri s.r.l. , a local shop specializing in leather goods. San Gimignano is known for its artisan products, and this shop was no exception. From wallets and handbags to belts and jackets, the quality of the leather was evident in every item. I ended up buying a beautiful leather journal, hoping to fill it with memories of our Tuscan travels. Emily, of course, found a stylish new handbag that she couldn’t resist.


Experience the art of Italian leather craftsmanship at Le Torri s.r.l. in San Gimignano, where quality meets tradition in stunning handmade goods.

As evening approached, we made our way to dulcisinfundo for dinner. This hidden gem, tucked away beneath brick archways, exuded a cozy and family-centric atmosphere. The menu featured authentic Tuscan cuisine made with herbs and olive oil from their small farm. We indulged in dishes like Pappardelle with Wild Boar Sauce and Pork Fillet with Vinsanto-glazed chicory. The flavors were rich and satisfying, a perfect end to a day of exploration. Oliver, surprisingly, enjoyed the wild boar sauce, a testament to the restaurant's skill in preparing traditional dishes with a touch of modern flair.


Discover authentic Tuscan flavors at Dulcis in Fundo in San Gimignano – where tradition meets culinary excellence.

Tomorrow, we plan to delve into some of the town's more unusual attractions, including the Museum of Torture and the Porta delle Fonti. I'm also looking forward to a relaxing drink at Bar La Cisterna. But for tonight, I'm content to savor the memories of today, a day filled with art, history, and the simple pleasures of Tuscan life.

“The real voyage of discovery consists not in seeking new landscapes, but in having new eyes.” I feel like today has given me just that – a new perspective on the beauty and history that surrounds us, if only we take the time to look.

Cheerio until tomorrow!