• San Gimignano - The driver will collect guests directly from their location and transport them through the picturesque Tuscan hills to San Gimignano, where they can enjoy free time for a self-guided exploration.

Renowned as the “Town of Beautiful Towers,” San Gimignano is a wonderfully preserved medieval village and a genuine open-air museum. Once boasting over 70 towers, it now offers stunning views, artisan shops, and local delicacies such as Vernaccia di San Gimignano wine, saffron, and Prosciutto d’Oro.

Visitors should not miss the opportunity to stop in the main square to savor the world-famous gelato at Gelateria Dondoli, or climb one of the towers for breathtaking panoramic views and a touch of local legend.

• Chianti Road - Later, the journey continues along one of Tuscany’s most beautiful Wine Roads, right through the heart of the Chianti region, symbolized by the famous Black Rooster.

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

The Sienese chose a white rooster, while the Florentines selected 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 departed early and traveled much farther, reaching a point just 12 km from Siena.

This clever tactic 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.

• Podere La Marronaia- Le Colonne Biodynamic Winery & Farm - For lunch, guests will visit a delightful family-run organic farm for an authentic Tuscan experience, blending local flavors with expert wine pairings. Enjoy a genuine meal while uncovering 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, allowing guests to taste, learn, and savor the region’s finest flavors.
• Monteriggioni - After lunch, the tour proceeds to Monteriggioni for a self-guided visit.

Established by the Sienese in 1213 as a fortress against Florence, Monteriggioni was once deemed 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.

• Badesse - The final stop will be at a small, family-run Chianti winery, where wine has been produced authentically for generations. Here, guests will 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 crafted in the traditional way—small quantities, exceptional flavor, and centuries of expertise passed down through generations.

After the tasting, guests will be returned to their location, concluding a full day of authentic Tuscan experiences.

• Local expert driver
• Private transportation
• Bottled water
• In-vehicle air conditioning
• Lunch
• Alcoholic beverages

• Everything not found under the heading inclusions is excluded

A full day trip traveling through the rolling hills of Chianti, among avenues of cypress trees, medieval villages, fields of sunflowers and legends. Tasting of the best Chianti wines with a delicious lunch in a family-run farm. This is the best private tour for couples, families or small groups of friends:
Itinerary:
• In the morning meeting with the driver at your hotel or another place of your choice (B&B or private apartment)
• We will cross the rolling hills of Chianti, among olive groves, cypresses and vineyards.
• We will visit the magnificent Towers of San Gimignano and the historic center.
• For lunch we will move to a real Tuscan farm, to understand the secrets of wine production and enjoy a lunch with typical Tuscan foods and 6 tastings of local wines.
• After lunch we will visit the invincible Monteriggioni Castle
• On the way back we will have a second wine tasting at a local winery, which produces its Chianti Classico wine following the old way.
Check out “What to Expect”

For a full refund, cancel at least 24 hours before the scheduled departure time.