Exploring the Medieval Charm of San Gimignano

A Day of Tuscan Exploration

Today was all about immersing ourselves in the heart of San Gimignano, discovering its hidden corners and savoring the authentic Tuscan experience. From breathtaking viewpoints to ancient churches and delightful culinary adventures, every moment was filled with beauty and charm. Daniel and I set out with a sense of excitement, ready to explore the artistic and historical treasures of this medieval town.

Our day began with a hearty breakfast at La Vecchia Nicchia di Alessandro Pieragnoli Enoteca - Bruschetteria. This cozy spot, nestled close to the Porta San Matteo, was the perfect place to start our morning. The aroma of freshly baked bread and brewing coffee filled the air as we settled into a small table. I ordered a classic bruschetta with ripe tomatoes and basil, while Daniel opted for one topped with creamy pecorino cheese and truffle oil. The ingredients were so fresh, and the flavors were incredible. Sipping on a strong, frothy cappuccino, we discussed our plans for the day, feeling energized and ready to explore.


Experience authentic Tuscan cuisine at La Vecchia Nicchia di Alessandro Pieragnoli in San Gimignano - a haven for food lovers and wine enthusiasts.

With our stomachs full and spirits high, we made our way to the first stop on our itinerary: the Viewpoint. As we ascended towards the Rocca di Montestaffoli, the panoramic views began to unfold before us. From this ancient fortress, perched atop a hill, we gazed upon the iconic towers of San Gimignano and the rolling hills of the Tuscan countryside. The vista was breathtaking, a tapestry of vineyards, olive groves, and terracotta rooftops stretching as far as the eye could see. I snapped photo after photo, trying to capture the sheer beauty of the landscape, while Daniel simply stood in awe, taking in the moment. The air was crisp and clean, carrying the scent of wildflowers and sun-baked earth. It was a moment of pure serenity, a reminder of why we love to travel and discover places like this.


Discover the stunning panoramic views of San Gimignano's historic skyline and breathtaking Tuscan countryside at this unmissable viewpoint.

Sometimes, the most beautiful discoveries are the ones you stumble upon unexpectedly.

Next on our list was the San Gimignano Chiesa di Sant'Agostino, a historic Catholic church that has been a significant local landmark since the 13th century. The church is located on the quaint Piazza Sant'Agostino. While its exterior may seem plain, the interior boasts elaborate and colorful frescos that adorn its walls. Stepping inside, we were immediately struck by the contrast between the simple exterior and the glorious interior. The church was peaceful and quiet, a welcome respite from the bustling streets outside. We wandered through the hallowed halls, admiring the intricate details of the artwork and the serene atmosphere. The highlight was undoubtedly the seventeen-panel fresco cycle on The Life of St Augustine around the high altar, painted by Benozzo Gozzoli between 1463 and 1467. Each panel told a story, a vibrant depiction of the saint's life and teachings. I found myself lost in the details, marveling at the skill and artistry of the painters. The Cappella di San Bartolo also caught our attention, housing the remains of the eponymous saint and featuring a magnificent altar by Benedetto da Maiano.


Explore the enchanting Chiesa di Sant'Agostino in San Gimignano, a stunning fusion of spirituality and medieval art set in the heart of Tuscany.

Leaving the church, we felt a sense of peace and reverence, grateful for the opportunity to witness such a beautiful and historically significant place. It was time for lunch, and Daniel had made a reservation at Osteria del Carcere, a restaurant known for its traditional Tuscan cuisine. The osteria is near Piazza della Cisterna. The restaurant itself was charming, with exposed stone walls and rustic wooden tables. We started with a selection of local cheeses and cured meats, accompanied by a bottle of Vernaccia di San Gimignano, the town's famous white wine. For our main courses, I chose the pappa al pomodoro, a classic Tuscan tomato and bread soup, while Daniel opted for the wild boar ragu with homemade pasta. Every dish was bursting with flavor, a testament to the fresh, local ingredients and the skill of the chef. The wine was crisp and refreshing, the perfect complement to our meal. As we savored each bite, we talked and laughed, enjoying the simple pleasure of sharing a delicious meal in a beautiful setting.


Experience authentic Tuscan cuisine at Osteria del Carcere in San Gimignano - where tradition meets flavor in a charming setting.

After lunch, we decided to explore Casa Santa Fina, a historical landmark that honors the life of Saint Fina, a beloved local figure known for her piety and miraculous story. As we approached the house, we were struck by its serene ambiance and classic medieval architecture. The interiors were beautifully preserved, offering a glimpse into the life of Saint Fina and the history of San Gimignano. We wandered through the rooms, reading about her life and admiring the artwork dedicated to her. The tranquil gardens provided a peaceful retreat, a place for reflection and contemplation. I found myself moved by the story of Saint Fina, a young woman who endured great suffering with grace and faith. It was a reminder of the strength and resilience of the human spirit, and the power of compassion and kindness.


Explore Casa Santa Fina in San Gimignano, a historical landmark dedicated to the saint known for her miraculous life and serene beauty.

Our afternoon took an unexpected turn when we stumbled upon a Truffle Boutique. Intrigued by the aroma wafting from within, we stepped inside and were immediately transported to a world of culinary delights. The shelves were lined with truffle-infused oils, sauces, pastes, and salts, each one more tempting than the last. The owner, a jovial man with a passion for truffles, greeted us warmly and offered us a tasting. We sampled truffle-infused olive oil with crusty bread, truffle cheese with local honey, and truffle balsamic vinegar with Parmesan cheese. The flavors were intense and earthy, a true indulgence for the senses. We learned about the different types of truffles, how they are harvested, and the best ways to use them in cooking. Inspired by our newfound knowledge, we purchased a few small jars of truffle delicacies to take home with us, eager to experiment with them in our own kitchen.


Discover the essence of Tuscan cuisine at Truffle Boutique in San Gimignano, where exquisite truffle products await every food lover.

As the sun began to set, we made our way to Ristorante Dorandò for dinner. Located in a historic building with 14th-century arched brick walls, the restaurant exuded an air of elegance and charm. We were greeted by the chef Duccio, who was very cordial and enlightened us about the history of Etruscan food, the restaurant and of his city. We started with the Quail and Onion Stuffed of Salt with her own Jam Sweet-sour and Celeriac of Truffle. I chose the lamb, while Daniel opted for the smoked duck. Each dish was a work of art, both visually stunning and incredibly delicious. The flavors were complex and nuanced, a testament to the chef's creativity and skill. The service was impeccable, and the atmosphere was romantic and intimate. It was the perfect way to end our day of Tuscan exploration, a celebration of food, wine, and the simple joys of life.


Experience authentic Italian cuisine in the heart of San Gimignano at Ristorante Dorandò – where every meal is a celebration of flavor.

Reflecting on the day, I felt a deep sense of gratitude for the experiences we had shared. San Gimignano had captivated us with its beauty, history, and culinary delights. From the breathtaking viewpoints to the ancient churches and the truffle-infused delicacies, every moment had been a treasure. As we walked back to our hotel, hand in hand, I couldn't help but smile, knowing that this was a day we would never forget.

Tomorrow, on our final day in San Gimignano, we plan to explore the Porta delle Fonti and Torri degli Ardinghelli, soaking in the last moments of this charming medieval town before we head back to London. We'll also be sure to enjoy a final Tuscan meal at Il Trovatore and a drink at Bar Le Torri. I'm already looking forward to it!