Family Adventure in the Medieval Town of San Gimignano

Echoes of the Past

Today, San Gimignano truly felt like stepping back in time. The medieval architecture, the bustling piazzas, and the stunning views all combined to create an unforgettable experience. As someone who grew up on a small island surrounded by the vast ocean, I'm always drawn to places with a strong sense of history and culture, and San Gimignano offered that in abundance. It was a day filled with exploration, delicious food, and moments that I know my family and I will cherish for years to come.

Our day began, as usual, with breakfast at Ristorante Bel Soggiorno. There’s something comforting about starting the day in a familiar place, especially when traveling. The pastries were fresh, and the coffee was strong – just what I needed to fuel our adventures. Zayn was particularly excited, chattering about climbing a tower and seeing the whole town from above. Aisha, ever the pragmatist, made sure we all had sunscreen on, a lesson we learned the hard way after nearly forgetting it on our first day [TripEssentialsForgotten].


Experience authentic Tuscan cuisine at Ristorante Bel Soggiorno in San Gimignano - where every dish tells a story.

Our first stop was the Bagolaro di San Gimignano - Albero monumentale, a truly majestic tree. I never thought I'd be so impressed by a tree, but this one was special. It’s not just any tree; it’s a centuries-old hackberry tree that stands as a natural monument. The Bagolaro, also known as the Celtis australis, boasts a massive trunk and a wide, round crown. I learned that it has been included in the Grandi Alberi del WWF project, ensuring its preservation for years to come. Zayn was fascinated by its size, and we spent a good half-hour just taking photos and admiring its grandeur. It was a peaceful start to what promised to be a busy day. Standing beneath its shade, I couldn't help but feel a sense of connection to the past, imagining all the people who had sought refuge under its branches over the centuries.


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

Next on our list was Piazza della Cisterna, the heart of San Gimignano. The triangular shape of the piazza is striking, and it’s surrounded by medieval buildings that seem to whisper stories of centuries past. The central feature, a public well built in 1287, is a testament to the town's ingenuity and community spirit.


Discover the enchanting Piazza della Cisterna in San Gimignano, a historical landmark bursting with medieval charm, local culture, and vibrant atmosphere.

The beauty of San Gimignano lies not just in its towers, but in the stories etched into every stone and corner of its piazzas.

The kids loved running around the open space, while Aisha and I took in the sights. There were a few vendors setting up stalls, adding a lively atmosphere to the historic square. According to what I have read, the piazza has hosted musical events and fairs. I imagined what it would have been like in the Middle Ages, filled with merchants, performers, and locals going about their daily lives. We stopped for a quick gelato at Caffetteria Gelateria dell'Olmo, which is located right on the piazza. The gelato was delicious, and we enjoyed it while people-watching. Zayn made a bit of a mess, of course, but that’s part of the fun of traveling with kids.


Discover the authentic taste of Italy at Caffetteria Gelateria dell'Olmo in San Gimignano, where exquisite gelato and delightful pastries await.

After our gelato break, we headed to the Palazzo Comunale, Pinacoteca, and Torre Grossa. This was perhaps the highlight of the day. The Palazzo Comunale, or Town Hall, is an impressive building that dates back to the 13th century. Inside, the Pinacoteca houses a remarkable collection of paintings from the Middle Ages and Renaissance. I was particularly struck by the works of Filippino Lippi and Benozzo Gozzoli. Each painting seemed to tell a story, offering a glimpse into the lives and beliefs of the people who lived here centuries ago. The Sala di Dante was particularly impressive, with its frescoes depicting tournaments and hunting scenes. Aisha, with her background as a nurse, was drawn to the details in the paintings, noticing the subtle expressions and gestures of the figures.


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

But the real highlight was climbing the Torre Grossa, the tallest tower in San Gimignano. The climb was challenging, especially with Zayn in tow, but the views from the top were more than worth it. From 54 meters high, we could see the entire town spread out before us, with its iconic towers piercing the sky. The surrounding countryside was a patchwork of rolling hills and vineyards, bathed in the warm Tuscan sun. It was a breathtaking panorama that I’ll never forget. Zayn, despite his initial enthusiasm, got a bit tired on the way up, but he perked up as soon as he saw the view. “It’s like a fairy tale!” he exclaimed, and I couldn’t have agreed more.

For lunch, we decided to try Chiribiri, a restaurant that had been recommended to us. It was a bit of a mixed experience. While the food was generally good – I particularly enjoyed the wild boar stew – the service was a bit slow. There were also mixed reviews about the staff. However, the atmosphere was cozy and charming, and we appreciated the traditional Tuscan cuisine. Zayn, predictably, ordered pasta with tomato sauce, which he devoured in minutes. Aisha and I shared a bottle of local wine, savoring the flavors of the region.


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

After lunch, we did a bit of shopping at Roby Shop Di Giacobbe Roberta. It was a small, local shop selling a variety of souvenirs and local products. I picked up a few postcards and a small ceramic tower to remember our trip. Aisha found a beautiful hand-painted scarf, which she immediately wore. Zayn, of course, wanted a toy sword, but we managed to steer him towards a less dangerous wooden toy.


Discover unique gifts and authentic Tuscan souvenirs at Roby Shop Di Giacobbe Roberta in San Gimignano, a true treasure for travelers.

As the day wound down, we stopped for a final treat at Caffetteria Gelateria dell'Olmo. This time, we sat outside and enjoyed our gelato while watching the sunset over the Tuscan hills. The sky was ablaze with color, and the air was filled with the sounds of laughter and conversation. It was a perfect ending to a perfect day.

For dinner, we chose Ristorante San Martino 26, which came highly recommended. This was a completely different experience from lunch. The restaurant had a cozy atmosphere, and the staff was incredibly welcoming. The food was exquisite, a modern take on traditional Tuscan dishes. I had the beef tartare, which was perfectly cooked. Aisha opted for the tasting menu, which she raved about for the rest of the evening. Zayn, surprisingly, tried the gelato and loved it. The service was fast and attentive, and the prices were reasonable. It was the perfect way to end our day of exploration.


Experience exquisite fine dining at Ristorante San Martino 26 in San Gimignano - where tradition meets innovation in every dish.

Travel is more than just seeing new places; it's about creating memories and sharing experiences with the people you love.

As we walked back to Hotel Bel Soggiorno, I reflected on the day. San Gimignano had exceeded all my expectations. It was a town that was both beautiful and fascinating, with a rich history and a vibrant culture. But more than that, it was a place where I could connect with my family and create memories that would last a lifetime. I thought about my childhood in the Maldives, surrounded by the ocean and a close-knit community. Traveling with Aisha and Zayn, I feel like I’m creating that same sense of belonging and connection for them, no matter where we are in the world.


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.

Tomorrow, we plan to explore more of San Gimignano, including the Torri degli Ardinghelli, the Chiesa di Sant'Agostino, and Porta San Giovanni. I’m particularly excited to see the Torri degli Ardinghelli, as I’ve read that they offer a unique perspective on the town's architecture. We also plan to visit a local shop, L'Emporio Di Campagna Di Sgaravatti Roberta & C. S.N.C., to pick up some local specialties. And, of course, we’ll be starting our day with breakfast at Ristorante Bel Soggiorno, our home away from home.

As I write this, Zayn is already asleep, dreaming of towers and gelato. Aisha is reading a book, a contented smile on her face. I feel grateful for this trip, for the opportunity to share these experiences with my family. San Gimignano has captured our hearts, and I know we’ll be talking about it for years to come.