Day trip

Florence: S. Gimignano, Siena, Chianti Lunch & Wine Tour

Activity provider: CAF Tour & Travel
Day trip

Florence: S. Gimignano, Siena, Chianti Lunch & Wine Tour

Activity provider: CAF Tour & Travel
Likely to sell out

From US$ 60.91 per person

Likely to sell out

Join a day trip into the heart of Tuscany, departing from Florence and visiting San Gimignano, Siena, and Monteriggioni. Relax in a Chianti winery for a typical lunch and a guided wine tasting.

About this activity

Free cancellation
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Duration 11 hours
Check availability to see starting times.
Live tour guide
English, Spanish, French


  • Visit two UNESCO World Heritage sites
  • Tour the beautiful Siena Cathedral, led by a local guide
  • Enjoy wonderful views of Tuscan rolling hills and Chianti countryside
  • Stop at a Chianti winery for lunch and a guided tasting of three different wines
Full description

Embark on a scenic guided tour from Florence to the charming Tuscan towns of San Gimignano, Monteriggioni, and Siena. Stroll around the historic villages and enjoy a delicious Chianti Hills wine and balsamic vinegar tasting. Upgrade your experience with tickets to Siena Cathedral.

Start at San Gimignano, the world-famous walled town located on a hilltop, which has remained intact through the centuries and is known for its tall towers, frescoes, and many other works of art. Take around 2 hours of free time to explore the city center.

Visit the historical walled hamlet of Monteriggioni. Cross Chianti’s rolling hills to a cozy winery where you can relax and enjoy three wines and balsamic vinegar, followed by a Chianti-style three-course lunch.

Enjoy a guided tour of Siena’s historic center (if selected in the option), starting with the 13th-century Basilica of San Domenico. Stroll along the narrow medieval streets of the city, flanked by splendid palaces and historic shops. Pass through the Piazza del Campo and visit the cathedral, if you select the option. 

Take some free time in Siena before returning to Florence.

  • Transportation by air-conditioned bus
  • Multilingual tour escort on board
  • Wine tasting
  • Lunch
  • Professional local guide in Siena (if option selected)
  • Siena Cathedral guided visit with entrance ticket (if option selected)
  • Hotel pickup and drop-off

Select participants and date



Meeting point

Meeting point may vary depending on the option booked.

Important information

What to bring

  • Comfortable shoes

Know before you go

  • The order of the itinerary may change
  • If your tour or language is not available, you will be offered an alternative tour or a full refund
  • For small groups of up to 8 people, the tour guide service can be replaced with an English-speaking driver-guide service, with the rest of the program remaining unchanged
  • From November to March, the itinerary does not include the stop at Monteriggioni and the return to Florence is approximately 30 minutes earlier 
Customer reviews

Overall rating

4.6 /5

based on 375 reviews

Review summary

  • Guide
  • Transportation
  • Value for money
  • Safety

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Star rating:

Our tour guide (Maria Luisa) was great. This was a useful and fun way to explore Tuscany and catch a ride to San Gimignano and Siena. Highly recommend. The lunch and winery are okay but clearly a very commercial/modern enterprise. If you care most about visiting the towns, I’d recommend this tour. If you’re mostly interested in visiting smaller, charming, old wineries in Tuscany, the other tours offered by this vendor are more suitable for those purposes. Either way, I’d definitely use this vendor again!

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February 28, 2023

Our guide (Sandro) was absolutely amazing and helpful which was a plus to this fabulous tour. He provided a lot of local info of the places. He planned every steps of our journey thoroughly to ensure none in the group gets lost. The wine tasting and lunch (vegetarian) was well catered for. Highly recommend the 30yr balsamic vinegar. Tour itinerary went exactly as described with ample free time to visit the cities. Coach itself was comfortable and easy to spot.

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January 27, 2023

Great day with Sandro. He has an excellent sense of humour and made sure all needs are cared for and that we stuck to times. We thoroughly enjoyed the lunch and the visits to the medieval towns. We explored Siena on our own and with guidance of Sandro it was easy. Highly recommended!

January 19, 2023

Product ID: 10680