"Ramble Through The Rolling Hills Of Chianti" with lunch and 2 wine tastings

Our driver will pick you up directly from your location and take you through the rolling hills of Tuscany to San Gimignano, where you’ll enjoy free time for a self-guided visit.

Known as the “Town of Beautiful Towers”, San Gimignano is a perfectly preserved medieval village and a true open-air museum. Once home to over 70 towers, today it offers breathtaking views, artisan shops, and local specialties such as Vernaccia di San Gimignano wine, saffron, and Prosciutto d’Oro.

Don’t miss a stop in the main square to taste the world-famous gelato at Gelateria Dondoli, or climb one of the towers for stunning panoramic views and a touch of local legend.

Later, we’ll drive along one of the most beautiful Wine Roads in Tuscany, right through the heart of the Chianti region, whose symbol is the famous Black Rooster.

According to legend, after years of conflict, Florence and Siena agreed to define their borders by sending two knights—one from each city—who would depart at sunrise when the rooster crowed. The new border would be set where the knights met.

The Sienese chose a white rooster, while the Florentines chose a black one. The Florentines, however, kept their rooster in the dark without food, so on the chosen day it crowed in the middle of the night. Their knight left early and rode much farther, reaching a point just 12 km from Siena.

This clever trick is said to explain why the border between Florence and Siena is not halfway between the two cities—and why the Black Rooster remains the enduring symbol of Chianti.

For lunch, we’ll visit a charming family-run organic farm for an authentic Tuscan experience, combining local flavors with expert wine pairings. Enjoy a genuine meal while discovering the secrets of Tuscan cuisine, winemaking, and olive oil production.
Lunch includes:
• Classic Tuscan dishes: bruschetta, homemade pasta , cured meats, pecorino cheese, dessert, and more
• Wine tasting: Chianti, Chianti Riserva, Sangiovese, Vernaccia
• Olive oil and balsamic tasting, including pepper olive oil and truffle oil
A full sensory experience that perfectly pairs Tuscan food and wine, letting you taste, learn, and savor the region’s finest flavors.

After lunch, we’ll head to Monteriggioni for a self-guided visit.

Founded by the Sienese in 1213 as a fortress against Florence, Monteriggioni was once considered impregnable. The Florentines could never conquer it through force alone—they succeeded only through deception. By bribing the Sienese captain Giovanni Zeti, they breached the walls, capturing the fortress, sacking the town, and taking many prisoners. Siena was forced to surrender to Florentine rule.

According to local legend, on full moon nights, the sounds of trampling hooves and ghostly moans can still be heard. They are said to be the restless spirit of Captain Zeti, unable to find peace after his betrayal.

Monteriggioni today is a perfectly preserved medieval village, offering a step back in time and stunning views from its walls.

Our final stop will be at a small, family-run Chianti winery, where wine has been produced genuinely for generations. Here, you’ll enjoy a second tasting featuring Classic Chianti, Chianti Riserva, other Tuscan wines, and the prestigious Super Tuscan, along with extra virgin olive oil.

Chianti wines are made the traditional way—small quantities, exceptional flavor, and centuries of expertise passed down through generations.

After the tasting, we’ll return you to your location, concluding a full day of authentic Tuscan experiences.n.