Exclusive Siena and San Gimignano Tour & Chianti Wine Experience

Highlights

Itinerary

1. 1

   The adventure begins in Siena, a city celebrated for its medieval charm and rich cultural heritage. A local guide will take you through its narrow streets, unveiling centuries of history. Admire the iconic Piazza del Campo, one of Europe’s most renowned squares, famous for hosting the thrilling Palio horse race. Marvel at the stunning Siena Cathedral, a Gothic masterpiece adorned with intricate details, marble floors, and priceless works of art by masters like Michelangelo and Donatello. Experience the lively atmosphere of this historic city, a proud rival of Florence throughout history.

   3 hours•Admission free

2. 2

   Stroll through Piazza Salimbeni and admire the stunning architecture of the buildings surrounding the square. The iconic Palazzo Salimbeni stands as a symbol of the town’s financial history, offering a glimpse into Siena’s rich past while providing a peaceful and picturesque setting in the heart of the city.

   30 minutes•Admission free

3. 3

   Siena Cathedral

   Follow your guide and admire from the outside the outstanding Duomo di Siena

   The Duomo di Siena, or Siena Cathedral, is one of the most remarkable examples of Italian Gothic architecture. Dedicated to the Virgin Mary, it was constructed between the 12th and 14th centuries and stands as a symbol of Siena’s rich history and artistic legacy.

   30 minutes•Admission not included•See on map

4. 4

   Continue your amazing journew with a visit to a traditional winery in the Chianti region, where you’ll indulge in a guided wine tasting experience. Savor the rich flavors of Chianti Classico and other local varietals, perfectly paired with regional delicacies like pecorino cheese, cured meats, and bruschetta. Learn the secrets of winemaking, from grapevine to glass, and embrace the traditions and passion that define this celebrated wine region.

   2 hours•Admission free

5. 5

   Next, travel through the idyllic Tuscan countryside to reach San Gimignano, a hilltop town often called the "Medieval Manhattan" for its iconic skyline of 14 ancient towers. Explore Piazza della Cisterna and Piazza del Duomo, stroll along charming streets lined with artisan shops, and admire the town’s remarkably preserved medieval architecture. The stunning views of vineyards and olive groves stretching out to the horizon will leave you spellbound, making San Gimignano an unforgettable highlight of your day.

   2 hours•Admission free

6. 6

   Make your way to Piazza della Cisterna, the heart of San Gimignano’s historic center, and savor the internationally acclaimed, award-winning gelato from Gelateria Dondoli.

   30 minutes•Admission free

7. 7

   Admire the Duomo of San Gimignano from the outside, with its impressive Romanesque facade and beautiful positioning in the heart of the town, offering a glimpse of its medieval charm and historical significance.

   30 minutes•Admission not included

8. 8

   Explore the Rocca di Montestaffoli, both from the outside and within, where you can appreciate its imposing structure and wander through its historic interior. From the top, enjoy breathtaking panoramic views of San Gimignano and the surrounding countryside, immersing yourself in the rich medieval heritage of the town.

   30 minutes•Admission free

9. 9

   Pubblico Palace

   Visit one of the most significant squares in the city of Siena and let yourself be captivated by the imposing "Torre del Mangia". Built between 1338 and 1348, it was designed to match the height of the Siena Cathedral's bell tower, symbolizing the harmony between religious and civic authority in the city.

   1 hour•Admission free•See on map

Meeting point

TOURS & NEWS KIOSK AT PIAZZALE MONTELUNGO BUS TERMINAL Located at 5-10 minutes walking distance from Santa Maria Novella Train Station. Look for our staff wearing a FUCHSIA CIAOFLORENCE JACKET and holding a CIAOFLORENCE CLIPBOARD!

The map shows Florence. The exact meeting point is the address above.Open larger map

Pickup

• Everyone meets at the start point

Know before you go

• Infants and small children can ride in a pram or stroller
• Public transportation options are available nearby
• Infants are required to sit on an adult’s lap
• Not recommended for travelers with spinal injuries
• Not recommended for travelers with poor cardiovascular health
• Travelers should have at least a moderate level of physical fitness
• Please inform us of any food intolerance or allergy in advance
• Please note that the given order of the visits may change
• Mobile or paper ticket accepted
• One per booking

Cancellation and refunds

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

• Cancelled and fully refunded if too few travellers book