The Enchanting Town in the Heart of Tuscany

Introduction

Located in the Tuscan hills of Italy is a quaint medieval town, with a population of a little over 7,000 residents. It is known for its well preserved architecture, especially its medieval towers, 14 of which remain of the original 72. For this reason, it became a UNESCO World Heritage site in 1990. The town is also famous for its beautiful frescoes, charming cobblestone streets, stunning landscapes, and the historic Piazza della Cisterna. The name of the town is San Gimignano.

Firsts

I first came to San Gimignano when I was about 20 years old on a family trip. I will never forget that first day. Vehicles are generally not allowed to drive in the town, so we had to park in a parking lot in one of the outskirts of the town and make the short trek to the entrance. The town itself is situated on a hilltop about 1,000 feet above sea level, so as you make your way up to it, you are greeted with the most stunning sweeping views of Tuscany. I remember standing in sheer awe and delight at the beautiful green rolling hills, vineyards, and endless fields of sunflowers! We stayed in a beautiful stone building that had been converted from a once lavish personal home to a hotel with several guest rooms. The magic of the city came alive at night. The lights danced on the cobblestone streets, and the air was filled with the music of street performers and the alluring scent of delicious foods. I also made fast friends with a friendly older gentleman who owned a souvenir shop in which everything, again to my pure delight, was sunflower themed. After only a few days in this town, I was smitten!

The Return

I always knew I would have to come back to San Gimignano if I ever had the chance. And that chance came about five years later, and with a new perspective. This time I was traveling with my husband! I was so happy to share this special place with the love of my life! We had already lived in a few other countries and decided to take a vacation to Italy. As we weren’t planning on renting a car, I chose a guided tour of Siena that included San Gimignano as a day trip from Florence, where we would be staying for a few nights. Unfortunately, the tour day was a bit rushed, and by the time we got to San Gimignano that afternoon, we only had about an hour or so. Needless to say, I was very disappointed. So…my husband insisted we book another day trip whose focal point was San Gimignano, and use our last day in the area to visit again. I was so happy! Our day trip back was lovely! We explored all around the streets together, took in all the angles, climbed to the top of the Torre Grossa, the tallest tower, standing at about 177 feet and drank in the panoramic views. And this time, I really enjoyed the local delicacies…the famous Vernaccia white wine, the cinghiale (wild boar) salami, and pecorino cheese infused with herbs, and my husband’s favorite…fresh truffles! I left that afternoon feeling much more satisfied with my return to this special place.

Third Time’s a Charm

Fast forward four years more years, and we had been through a pandemic, living in two more foreign countries, learning new languages, job changes, visa challenges, and on the cusp of another move. With all our belongings with us, two large and two small roller bags, and a backpack each, we decided to make a stop off in Italy. This time, I knew exactly what to do…I immediately booked a rental car and two nights in one of the local lodgings in the heart of San Gimignano. This really is the best way to see the town. During the day, the streets are filled with the tourists coming for the day trips, but after about 5pm, the town becomes much quieter, and you really get to experience its charm and enchantment. As we walked hand in hand through the narrow stone pathways lit by the warm glow of the street lamps, I thought back on my times in this small town on a hilltop…How I had learned and grown, how the chapters of my life had changed, who I had been and now become, and how the what was to come would shape me. Despite the changes and uncertainties in our life, this town held a timelessness that quieted my mind and heart and filled it with serenity. We enjoyed a romantic dinner in a lovely little cafe and a gelato in the piazza, and then we meandered through the streets until we made it back to our guesthouse. The next day we enjoyed some of the nearby sights and again spent the late afternoon and evening wandering the streets, following our senses into the shops, trying local olive oils, wines, cheeses, meats, coffee and baked goods, and being drawn in by the colorful displays of works of local artisans, ceramics, jewelry, paintings, postcards, and crafts. With our mouthwatering souvenirs, we made our own charcuterie board dinner at home as we savored our final evening in San Gimignano, looking out of our lattice window to the courtyard below and the soft pastels of the sun setting over the tower spotted Tuscan horizon beyond.

Conclusion

Some feel that San Gimignano is just another tourist trap, a town overrun with souvenir shops and expensive restaurants. Others feel that is historically valuable, a picturesque town with well preserved architecture, cultural experiences, and beautiful vistas. To me, San Gimignano is more than just a beautiful medieval town. It is a place that has captured my heart and given me the gift of tranquility, wonder, and reflection. Its enduring charm has drawn me back again and again. And what about for you? I cannot make that judgement call for you, my dear reader, I can only hope my experience will inspire you to explore, to discover what your unforgettable places are. As for this Tuscan gem…until next time, my beloved San Gimignano!