Day 5 in Florence was all about venturing into the Tuscan countryside for a day filled with history, wine, and medieval charm. This day trip, that I booked through Get Your Guide, took me to Siena, Monteriggioni, and San Gimignano—each stop offering something unique and unforgettable.
First up was Siena, a beautiful medieval city famous for its stunning Siena Cathedral (Duomo di Siena). This Gothic masterpiece is one of the most breathtaking cathedrals in Italy. Its striking black-and-white striped marble facade, intricate carvings, and detailed mosaics are truly works of art. Inside, the beauty continues with impressive frescoes, marble floors, and the famous Piccolomini Library. The cathedral dates back to the 13th century, and walking through it feels like stepping back in time.
Don’t miss the Piazza del Campo, the heart of Siena, where the famous Palio horse race takes place twice a year.
After Siena, we headed to Monteriggioni, a small medieval village that feels like something out of a fairy tale. This walled village, with its perfectly preserved fortress, was built in the 13th century to protect the region from invasions. We stopped at Poggi ai Laghi Winery for a wine tasting and lunch, and I can’t say enough good things about it. The Tuscan wines, paired with delicious local cuisine, made for an unforgettable experience. We tasted the sparking wines, the Oletta ChiantiRiserva DOCG and the Aranda Supertuscan wines. I loved both the Arella Spumante Cuvée Extra Dry and the Firmina Rose Sparkling wines, and the Oletta over the Aranda wine. We also tasted Frantoiano Biologico, Extra Virgin Olive Oil and Balsamic Vinegar Of Modena PGI Aged Silver, which was delicious! There’s nothing like sipping wine, and enjoying a delicious lunch with a view of the Tuscan hills!
Next, we explored Monteriggioni Castle, which has a long history as a strategic fortress for the city of Siena during its conflicts with Florence. You can still walk along part of the walls and take in the panoramic views of the rolling countryside. The small village inside the castle walls is like a step back into medieval Italy, with its narrow streets and stone buildings.
The final stop of the day was San Gimignano, known for its famous medieval towers. At its peak, San Gimignano had 72 towers, but today 14 remain, giving the town its nickname, the “Medieval Manhattan.” This UNESCO World Heritage site is packed with history, charm, and amazing views of Tuscany. I wandered through the cobblestone streets, explored the main piazza, and treated myself to more gelato from Gelatoria dell Olmo, which Advertises as being the best ice cream in the world. I tried Bailey’s Irish Crème and Carmel and they were delicious! San Gimignano is also known for producing the white wine Vernaccia di San Gimignano, so it’s a great place to try more local wine.
This day trip was the perfect way to experience the magic of Tuscany beyond Florence. Each stop was rich with history, culture, and, of course, delicious food and wine. I loved all our stops today, and can totally recommend this adventure when you are in Florence.
