4.9(28 reviews)
Siena, San Gimignano & Chianti Wine Tour
From€125
8 hours
Florence, Italy
About this activity
Experience the charm of Tuscany with a guided tour of Siena and San Gimignano, complemented by a delightful Chianti wine tasting.
Highlights
- Explore Siena's historic center
- Visit San Gimignano's medieval towers
- Enjoy Chianti wine tasting
- Discover Tuscan countryside
- Learn about local history and culture
Full description
Discover the enchanting Tuscan countryside on this full-day excursion from Florence. Begin with a guided tour of Siena's historic center, renowned for its stunning architecture and rich history. Then, visit the medieval town of San Gimignano, famous for its well-preserved towers and picturesque streets. The day culminates with a visit to a local Chianti vineyard, where you'll savor exquisite wines and learn about traditional winemaking techniques. This tour offers a perfect blend of history, culture, and gastronomy, providing an unforgettable Tuscan experience.
Included / Excluded
- Guided tour of Siena's historic center
- Visit to San Gimignano's medieval towers
- Wine tasting at a Chianti vineyard
- Lunch and personal expenses
Itinerary
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.
Duration: 3 hoursAdmission: NOT_APPLICABLE
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.
Duration: 30 minAdmission: NOT_APPLICABLE
3
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.
Duration: 30 minAdmission: NO
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.
Duration: 2 hoursAdmission: NOT_APPLICABLE
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.
Duration: 2 hoursAdmission: NOT_APPLICABLE
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.
Duration: 30 minAdmission: NOT_APPLICABLE
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.
Duration: 30 minAdmission: NO
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.
Duration: 30 minAdmission: NOT_APPLICABLE
9
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.
Duration: 1 hourAdmission: NOT_APPLICABLE
Meeting point
Start Location
Unknown location
Important information
Know before you book
- Tour operates rain or shine; dress appropriately for the weather.
- Minimum booking may apply; check availability for your group size.
- Confirm the meeting point and time upon booking.
Know before you go
- Wear comfortable walking shoes for cobblestone streets.
- Bring a camera to capture scenic views and historic sites.
- Check the weather forecast and dress accordingly.
Cancellation policy
Free cancellation up to 1 days before the activity starts
For a full refund, cancel at least 24 hours before the scheduled departure time.
Accessibility
- Stroller Accessible
- Easy Public Transport
- Infants Required On Laps
Good to know
- Please inform us of any food intolerance or allergy in advance
- Please note that the given order of the visits may change
Traveler reviews
4.928 reviews
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Amazing Siena and Countryside Tour
My family and I booked a private tour to visit the beautiful countryside and see towns like Siena and San Gimignano. Our tour guide Cristian, was so knowledgeable and he really helped us see the beauty of Italy and its different wonders. He was so easy and fun to talk to as we bonded over our culture and background. We were so grateful to have gotten him as our tour guide and we couldn’t have asked for a better one 💓💓
ayaz628Jun 23, 2026TRIPADVISOR
Wonderful experience
Christian took excellent care of us, gave us great suggestions and treated us like family.
toddbU2786OWJun 17, 2026TRIPADVISOR
Fabulous Tour!
Christian was a great guide and provided a lot of helpful information. He enhanced our first time in Italy both on the way to our destination and gave helpful recommendations for the rest of our trip.
Departure01850751297Jun 17, 2026TRIPADVISOR
Wonderful time
Our guide Cristian picked us up at our hotel and the fun began. He was a safe and efficient driver and we enjoyed hearing about the sights and region as we drove. We made a few stops to walk around and he advised us on where to go and what to do. The ride was safe, clean and well organized. The lunch at the winery was delicious and in a beautiful locale. We were dropped off safely back at our hotel tired and happy!
courtneyb732Jun 5, 2026TRIPADVISOR
Recommended excursion!
We visited Siena and the surrounding areas with the guide Constantino and Jean Carlos. Excellent experience! Highly recommended!
Coastal780355May 27, 2026TRIPADVISOR
Additional information
Please inform us of any food intolerance or allergy in advance
Please note that the given order of the visits may change