Siena Sunset & Chianti Wine Tour

From€71.2
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

4.1
326 reviews
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25

Afternoon wine tasting in Chianti

The experience was wonderful, the places were beautiful. The guide, Antonio, was always attentive to provide the tour instructions in both English and Spanish. Although the tour is advertised in Spanish, most of the wineries we visited conducted their tours in English, which is not complex to understand, and in case of any doubts, you can ask the relevant questions. The guide was always nearby to answer our questions in Spanish and translate for us if necessary. For wine lovers, it is 100% recommended.

mariojL5558WDMay 14, 2026TRIPADVISOR

Exceeding expectations

Was a perfect way to see Tuscany, taste wine, make friends, and have a delicious meal! (I’m stuffed)

Ericb12345Apr 28, 2026TRIPADVISOR

Lovely stuff

Great experience we had lovely wine, the family business so good in explaining everything

saimons1204Apr 15, 2026TRIPADVISOR

Dinner at the vineyard.

I figured we should have arrived at the winery, I think it would have been more interesting. The dessert left nothing to be desired but the rest of the dinner was delicious. The guide Julia and the driver Ricardo are pretty cool.

381fabioladOct 25, 2025TRIPADVISOR

Beautiful visit to Siena with winery

Had a nice time on the Chianti wine tour with trip to Sienna! Sebastian was a great tour guide, very informative and interesting. Roberto was an excellent driver. The trip to Siena was nice if you only have limited time as it just gives you a taste of the beauty of Siena. I do wish we would have had more time, but I knew booking the trip it was minimal. The winery was very nice. Wine delicious and the food was fantastic. My husband has food allergies and we are vegetarian. The winery was very accommodating to our needs and the food was plenty and delicious. The tour company verified our request and Sebastian also confirmed with each passenger on the bus to see if there were food allergies. We met some really great people over dinner as well. Great tour!

denisedianemOct 15, 2025TRIPADVISOR

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