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San Gimignano’s Towers, Hills, and Vines: Day Trip

Updated: Jan 9, 2025


We are off to San Gimignano, our home base for the next 3 nights. We will be picked up by our Van Driver, Gabriele Alessandroni. Not only is Gabriele an officially listened tour operator and driver, but he is a well respected WSET Level 4 Diploma Sommelier. He runs Wine School Italia, a local wine program in Florence. Now you’re entirely surrounded by passionate sommeliers, get your questions ready!



The ride to San Gimignano is roughly an hour to an hour and a half, but is smooth and full of beautiful scenery. Upon arriving to San Gimignano, its Medieval skyline demands your attention. Today, 14 of the original 72 towers are still standing in this UNESCO World Heritage site. The towers were once a symbol of wealth and power for the noble families and upper middle-class merchants whom controlled the free town. Nowadays, they are perfect for exploration and good photos!



During the day, San Gimignano can at times be a bit overrun by crowds and feel touristy, but don’t worry, we will be returning multiple evenings when all of the locals come out for an aperitivo and people watching. To show you the real side of town, we found one of the most charismatic and lovable locals possible, Filippo. This man is every bit of the word, authentic. Filippo is a walking dictionary of knowledge, especially when it comes to his hometown. Don’t believe us? Ask him where he lives. His apartment is part of the actual wall of San Gimignano. It doesn’t get more real than that.



You are in for an incredible day in San Gimignano, discovering its history, as well as the culture of Tuscany, the Renaissance and Italy as a whole. Please ask Filippo as many questions as possible, but try not to get him started on mushrooms. If the weather is just right, he might drag you into the forest the following morning to search for Porcini ;)



Walking through a town full of medieval history will have your stomach growling. We are off to a big lunch, wine tasting, and our home base for the next 3 nights. Fattoria di Fugnano is not only an incredible winery, but also an agriturismo with one of the most stunning views in the area. Before moving into our rooms, we will embark on a guided tour of the winery and farm accompanied by a a big lunch and tasting of 7 different wines. Wine from different vintages will probably be pulled out as well knowing the producer, Laura, and her son, Andrea. Get ready for an extremely fun tasting, you will absolutely need a siesta afterwards!



Fattoria di Fugnano is Sicilian woman owned since 1997 by Laura dell’Aira. The farm was obtained by her grandfather post World War Two and was originally a village dating back to the 1400’s. After he obtained one house of the village and continued to purchase the rest, he turned the land into a farm for meat and produce. He planted a few vines for himself, a couple friends and a restaurant in the area. This vine is still used in production today at 75+ years. After he died, Laura, 23 years old at the time, decided to move up to Tuscany from Sicily and turned the farm into a full on winery. 27 years later, she is renowned in San Gimignano as one of the best producers.



We will be enjoying a beautiful selection of wines from Fattoria di Fugnano. Originally from Sicily, Laura is known around San Gimignano as one of the top producers thanks to her unforgettable Vernaccia di San Gimignano. This special grape variety thrives in the ancient sea bed of the surrounding hills of San Gimignano. Known as the White Queen of Tuscany amongst a sea of Red Kings, Vernaccia is famous for its “sting and bite” of refreshing acidity. Vernaccia di San Gimignano is one of Italy’s most beloved white wines as it was the very first DOC wine of Italy, yet it is lesser-known in the international market. Big change is coming, however, as Vernaccia is making a big push forward in the coming years. All grapes are organically and sustainably sourced from the stunning farm itself, spreading across 450 acres of land, 55 of which are dedicated to the vines. Luckily for you, after the tasting, you will find more bottles in your room ;)



After our lunch and overwhelming amount of wine, the next few hours are yours. You can go back into town for some shopping, follow one of the surrounding hiking trails linked up to the ancient Roman road and medieval pilgrimage route, Via Francigena, or you can walk through the vines and drink more wine with Laura. However, we can all but guarantee you will want to sleep off some of that food/wine, or take in the stunning view of San Gimignano and its surrounding hills from your rooms. You will definitely need to knock off the food somehow, as Laura and her team are preparing an authentic Tuscan barbecue for our dinner.



We will all meet back up with Laura and her team for an incredible evening of food, wine, family and friends. There aren’t many better things in life than taking in a colorful Tuscan sunset with good company and a full stomach.


This day trip is part of our Grand Tour, and Gems of San Gimignano, Chianti Classico, and Chianti adventures. To learn more about these tours, click below!







 
 
 

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