Siena Sunset & Chianti Wine Tour
From€89
6 hours
Florence, Italy
About this activity
Experience the charm of Siena and the flavors of Chianti on this evening tour from Florence, featuring a guided city tour, wine tasting, and a traditional dinner.
Highlights
- Explore Siena's historic center
- Enjoy panoramic Tuscan landscapes
- Taste renowned Chianti wines
- Savor authentic Tuscan cuisine
- Witness a breathtaking Tuscan sunset
Full description
Discover the enchanting city of Siena and the renowned Chianti wine region on this immersive evening tour from Florence. Begin with a guided exploration of Siena's historic center, where you'll marvel at its medieval architecture and learn about its rich history. Then, journey through the picturesque Tuscan countryside to a local vineyard, where you'll indulge in a wine tasting session featuring the region's finest Chianti wines. Conclude your evening with a traditional Tuscan dinner at a local restaurant, savoring authentic dishes that capture the essence of Tuscany. This tour offers a perfect blend of culture, cuisine, and scenic beauty, making it an unforgettable experience for travelers seeking to immerse themselves in the heart of Italy.
Included / Excluded
- Round-trip transportation from Florence
- Guided tour of Siena's historic center
- Visit to a Chianti vineyard with wine tasting
- Traditional Tuscan dinner at a local restaurant
- Personal expenses and gratuities
Itinerary
1
For those of you looking for a breathtaking tour of Tuscany during the golden hours of the afternoon, this tour is perfect for you! Meet your friendly tour guide at Piazzale Montelungo Bus Terminal. Piazzale Montelungo is located 5-10 minutes walking distance from Santa Maria Novella train station. Grab a seat on the comfortable coach bus, and prepare to depart! During your journey to Siena, your guide will dive into the fascinating history of the city, with some interesting facts and information. The drive will take about one hour.
Duration: 1 hourAdmission: NOT_APPLICABLE
2
A truly unforgettable evening awaits you… You will be brought to 2 rustic wine estates in the heart of the Chianti wine region. Travel through one of Italy’s most iconic landscapes, dotted with vineyards, olive groves, and charming rural scenery, while your escort provides insights into the region and its traditions.
Duration: 1 hourAdmission: NOT_APPLICABLE
3
Arrive at the first local winery in the heart of Chianti. Enjoy a guided visit of the estate and learn about the winemaking process, followed by a tasting of excellent Tuscan wine.
Duration: 2 hoursAdmission: NOT_APPLICABLE
4
A truly unforgettable evening awaits you… You will be brought to a second rustic wine estate in the heart of the Chianti wine region. The estate overlooks the rolling hills and lush land. You will be seated at a prepared table among the vineyards of the estate. Does it get much better than this? One of the local wine producers will serve the appetizers of local, seasonal products such as bruschette, salami, and fresh cheese. Then, indulge in a home cooked pasta dish, all made with local products from the region. And the best part - your dinner will include a tasting of various high-quality wines, including Chianti Classico. Enjoy this fantastic meal under the glowing, colorful sky of Tuscany as the sun falls into the horizon.
Duration: 2 hoursAdmission: NOT_APPLICABLE
5
After your delicious (and picture-perfect!) dinner under the Tuscan sunset, it will be time to head back to Florence. You will arrive back in the early evening.
Duration: 1 hourAdmission: NOT_APPLICABLE
Meeting point
Start Location
Unknown location
Important information
Know before you book
- Tour operates in English; ensure you understand the language.
- Confirm the meeting point and time upon booking.
- Inform the operator of any dietary restrictions in advance.
Know before you go
- Wear comfortable walking shoes for the city tour.
- Bring a camera to capture the stunning Tuscan landscapes.
- 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
- Infant Seats Available
Good to know
- Please advise any specific dietary requirements at time of booking
- English and Spanish are always guaranteed. In order to confirm the excursion in Portuguese or French a minimum of 4 pax is required
Traveler reviews
4.1335 reviews
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Tuscan Winery Tour with Sophia
Great time spent with family on this winery tour Experienced professionals provided details of traditional Tuscan wine making. How to pair the wines and enjoy with and without food. Plenty of food provided.
Mary GJun 27, 2026TRIPADVISOR
Great afternoon tour!
Cecelia was very welcoming and knowledgeable about the trip. The vineyards were absolutely stunning and the food and wine were delicious.
salvatoretV1452ACJun 27, 2026TRIPADVISOR
Fabulous Tour of Chianti
We had a wonderful time on our tour. Cecilia was a fabulous tour guide and was excellent at explaining local history and all the ins and outs of the Chianti Region.
christinamN902LWJun 27, 2026TRIPADVISOR
Chianti Delights Tour
Cecilia was amazing!! She made it such an enjoyable experience. Her personality was so bubbly and she was the sweetest!
827abigailiJun 27, 2026TRIPADVISOR
Fun tour
We had a great experience and meal. Our guide Tereza was fantastic. Vladimir our driver was also excellent.
D9732CVbrianpJun 11, 2026TRIPADVISOR
Additional information
Please advise any specific dietary requirements at time of booking
English and Spanish are always guaranteed. In order to confirm the excursion in Italian, German, Portuguese or French a minimum of 4 pax is required
Important notice: Starting from April 2026, the tour itinerary will be modified. The stop in Siena will be removed and replaced with a visit to a winery, where a wine tasting will be included. Dinner will also be provided at the second winery