Siena, San Gimignano & Chianti Wine Tour
About this activity
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
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
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.
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.
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.
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.
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.
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.
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.
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.
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.
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
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
Amazing private day tour 10/10
Our private day tour was remarkable and a 10/10. Our amazing tour guide was Cristian and he was lovely. We saw multiple different historic sites, many breathtaking views, and stopped at Terra Di Sovernaja for a wine and olive oil tasting. Cristian did a great job accommodating what we wanted and sharing much information about the country and its history!
10/10 would recommend
great experience - our guide cristian was knowledgeable and such a fun addition to our private tour! he recommended several spots in each stop - really great recommendations! if you can, i’d recommend doing the private tour so you’re able to customize your lunch!
Florence day trip
Cristian was our guide and he explained the areas we visited and their history very well. He helped us personalize the experience to our tastes! Highly recommend.
Highly recommend!
Excellent tour!! Sarah was nothing short of amazing! It was a well executed tour and my family thoroughly enjoyed it! It was a nice balance of all three places!
An unforgettable experience in Siena with Ciao Florence Tour! 🌟
I would like to share my amazing experience with Ciao Florence Tour on your tour to Siena with visit to a winery. From the beginning, everything was perfect. Booking was super easy through their website, it is a very intuitive and fast process! 😊 Our guide, Cecili, was exceptional. His knowledge of the history and culture of Siena was impressive, and his infectious enthusiasm made us feel as if we were discovering the city for the first time. The visit to the winery was a highlight of the tour, we could taste some of the best wines in the region and learn about the process of making them. What I liked the most was the attention to detail of Ciao Florence Tour. The times were perfectly measured so that we could enjoy each stop without feeling rushed. The combination of culture, history and gastronomy was perfect. In short, if you are planning to visit Siena, don’t hesitate to choose Ciao Florence Tour. Cecili and his team will make your experience unforgettable. Thank you for such a wonderful experience! 🙏 Recommendation: Book now through their website and do not miss this experience!