Family Adventure in San Gimignano: Exploring Tuscany's Medieval Charm

A Tuscan Breeze on Two Wheels

Today was all about embracing the Tuscan spirit, and what better way to do that than with a Vespa? The family and I embarked on a Tuscany Vespa Cycle and Bike Tour, ready to explore the countryside in true Italian style. I was a little nervous at first, having not ridden a scooter in years, but the allure of the rolling hills and cypress-lined roads was too strong to resist.

The morning started with a hearty breakfast at Chiribiri. The aroma of freshly baked bread and strong Italian coffee filled the air. Omar was particularly excited about the pastries, while Fatima enjoyed a classic cappuccino. After fueling up, we made our way to the Vespa tour meeting point. The guides were fantastic, giving us a thorough safety briefing and a chance to practice before hitting the open road. I must admit, I stalled the Vespa a couple of times, much to Omar's amusement, but soon I got the hang of it.

With helmets on and engines revving, we set off into the Tuscan landscape. The sun was warm on our faces, and the breeze carried the scent of wildflowers and vineyards. It was an incredible feeling, zipping along those winding roads, with the iconic towers of San Gimignano always in view. Fatima, riding pillion with me, was snapping photos at every turn, while Omar, safely tucked between us, pointed out every little detail that caught his eye.

It's not just about seeing a place; it's about feeling it, breathing it, and becoming a part of its story.

Our first stop was a charming little vineyard nestled among the hills. We parked our Vespas and took a tour of the estate, learning about the winemaking process from grape to glass. Of course, no visit to a vineyard would be complete without a tasting. We sampled a few local wines, including the renowned Vernaccia di San Gimignano. Omar, of course, stuck to grape juice, but even he appreciated the stunning views from the vineyard.

After the wine tasting, we continued our Vespa adventure, making our way back towards San Gimignano. We parked our Vespas near Piazza Sant'Agostino, a peaceful oasis away from the bustling main streets. The piazza is surrounded by historic buildings, including the Church of Sant'Agostino, which we decided to explore. The church's simple facade belies the artistic treasures within, with beautiful frescoes and sculptures adorning the walls. Omar was fascinated by the stories depicted in the frescoes, and Fatima and I were impressed by the serene atmosphere of the church.

Lunch was at La Mangiatoia, a delightful restaurant known for its traditional Tuscan cuisine. We indulged in a feast of homemade pasta, grilled meats, and fresh vegetables, all washed down with more local wine. The atmosphere was warm and inviting, and the staff made us feel right at home. Omar devoured his pasta, declaring it the best he'd ever tasted.

With our bellies full, we decided to take a leisurely stroll through Parco della Rocca, a green oasis offering panoramic views of San Gimignano and the surrounding countryside. The park is located on the site of an old fortress, and remnants of the walls can still be seen. We wandered along the paths, enjoying the peace and quiet, and taking in the breathtaking scenery. Omar, ever the adventurous one, climbed to the top of one of the old towers, declaring himself the king of the castle.

As the afternoon wore on, we made our way to D! Vineria enoteca, a cozy little bar where we enjoyed an aperitivo before dinner. We sipped on local wines and nibbled on tasty snacks, while watching the world go by. It was the perfect way to unwind after a day of exploring.

For dinner, we chose Osteria del Carcere, a unique restaurant located near a former prison. The atmosphere was rustic and charming, and the menu featured traditional Tuscan dishes with a modern twist. I opted for a hearty ribollita, while Fatima chose a delicate fish dish. Omar, of course, had his favorite pasta. The food was delicious, and the service was impeccable.

As we walked back to Hotel Leon Bianco, under the starlit Tuscan sky, I reflected on the day's adventures. From the thrill of the Vespa tour to the peacefulness of Parco della Rocca, it had been a day filled with unforgettable experiences. Sharing these moments with my family made it even more special. I am so grateful for these opportunities to show Omar the world and create lasting memories together. Even though Fatima misses her teaching job back in Bielefeld, I think she is happy that we are taking the time to travel as a family and experience new cultures.

Tomorrow is our last day in San Gimignano. We plan to visit Vernaccia di San Gimignano Wine Experience La Rocca, Porta delle Fonti, and Beautiful View. I am looking forward to another day of exploration and discovery in this beautiful corner of Tuscany. I also plan to buy Fatima a nice leather bag at Maria's Pelletterie San Gimignano & Volterra as a thank you for all of her support. I can't believe our trip is almost over, but I know that the memories we've made here will last a lifetime.

I'm already looking forward to sharing more stories and photos from our travels. Until then, arrivederci from San Gimignano!


Experience the beauty of Florence and Tuscany on two wheels with the Tuscany Vespa Cycle and Bike Tour, an unforgettable adventure for all travelers.


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


Experience the enchanting Piazza Sant'Agostino in San Gimignano, a captivating square steeped in history and stunning medieval architecture.


Experience authentic Tuscan flavors at La Mangiatoia, a top-rated Italian restaurant nestled in scenic San Gimignano.


Discover the tranquility and historical richness of Parco della Rocca in San Gimignano, a perfect blend of nature and medieval charm.


Explore D! Vineria enoteca in San Gimignano for an exquisite selection of wines and traditional Italian cuisine in a charming atmosphere.


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


Discover the enchanting Hotel Leon Bianco in the heart of San Gimignano, perfect for travelers seeking comfort, convenience, and captivating local attractions.