Day trip

Florence: Siena, San Gimignano, & Monteriggioni Day Tour

Activity provider: My Tour in Italy

Florence: Siena, San Gimignano, & Monteriggioni Day Tour

Activity provider: My Tour in Italy
Likely to sell out
Likely to sell out

From US$ 53.41 per person

Enjoy a full-day tour of Tuscany’s villages and wine regions in the heart of the Tuscan countryside. Visit San Gimignano and the medieval town of Siena.

About this activity

Free cancellation
Cancel up to 24 hours in advance to receive a full refund
Covid-19 precautions
Special health and safety measures apply. Learn more
Reserve now & pay later
Reserve now & pay later to book your spot without any charges today. Learn more
Duration 11 hours
Check availability to see starting times.
Live tour guide
Spanish, English, Italian, Portuguese, French
Small group available

What customers loved


8.5 hours
  • Florence

  • 1 hour
  • San Gimignano (free time)

  • Monteriggioni Castle (free time)

  • Poggibonsi (wine tasting)

  • Siena (guided tour, free time)

  • 1.5 hours
  • Florence

Meeting point
Main stop
Other stop
  • Escape the bustle of Florence for a day and explore the beautiful Tuscan countryside
  • Drive through the gently rolling hills of the Val D’Elsa in luxury, air-conditioned coaches
  • Visit the medieval town of San Gimignano, home to Vernaccia di San Gimignano wine and saffron
  • Explore the immaculate town of Siena, world-renowned for its Palio horse race
  • Visit a splendid Chianti estate and take part in two exclusive wine tastings
Full description

Explore the heart of beautiful Tuscany on a full-day tour of the towns of San Gimignano and Siena, then discover the bucolic wine region of Chianti. Depart from Florence by an air-conditioned bus to your first stop, the UNESCO World Heritage Site of San Gimignano.

Discover one of the most splendid examples of an Italian medieval town. Distinguished by its famous towering skyline, San Gimignano stands along the Via Francigena on the hills of the Upper Val D’Elsa.

Get acquainted with the Tuscan environment with the town’s Vernaccia di San Gimignano wine, saffron, and Santa Fina pottery. Enjoy some free time to stroll through the town on your own and see its beautiful squares, architecture, churches, and side streets.

Afterward, head out to a unique location in the Chianti countryside to enjoy a wine tasting. Once you hop off the bus, be guided around a splendid winery. Get introduced to the estate's fascinating history and background.

Head inside the cellars to learn the secrets of Chianti winemaking together with the local host. Then enjoy a delicious wine tasting of Chianti Classico.

Continue to Siena for a guided tour of its enchanting architectural styles, including the Cathedral (exterior only) and Palazzo Comunale (Municipal Building, exterior only) in Piazza del Campo. The famous shell-shaped square provides the stage for the thrilling Palio horse race, run twice every summer.

  • Air-conditioned bus or minivan
  • Multilingual guide
  • Lunch (if option chosen)
  • Guided tour of Siena (if option chosen)
  • Free time in San Gimignano
  • Visit to the Monteriggioni fortress
  • Wine tastings
  • Guided visit of a Chianti estate
  • Entry to Siena Cathedral
  • Entry to Palazzo Comunale
Not suitable for
  • Wheelchair users
Covid-19 precautions
Safety measures in place
  • All areas that customers touch are frequently cleaned
  • You must keep social distance while in vehicles
  • The number of visitors is limited to reduce crowds
Traveler requirements
  • You are required to bring and wear a mask
  • You must fill out a travel information form

Select participants and date



Meeting point

Meeting point may vary depending on the option booked.

Important information

What to bring

  • Comfortable shoes
  • Comfortable clothes

Know before you go

  • This tour will be conducted in multiple languages at the same time
  • The tour itinerary may change according to the season and unforeseen circumstances
  • Customers must be able to climb and descend stairs
  • In the absence of the documents required for the security measures, it will not be possible to participate in the activity and no refund will be made
Customer reviews

Overall rating

4.4 /5

based on 3005 reviews

Review summary

  • Guide
  • Transportation
  • Value for money
  • Safety

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Star rating:

I highly recommend this tour company for a tour of the Tuscany countryside! We originally booked a tour that didn't include Pisa or lunch but they switched us to this tour for no additional cost because of a technical issue. We were so grateful for the clear communication and the alternative offer! It was a long day, so be prepared with snacks, water and comfortable shoes. We got an hour in Pisa and an hour in San Gimignano, which was my favorite stop on the trip! Both were a little rushed but understandable with the many stops throughout the day. A 3 course lunch with wine was provided, the food was okay but overall still worth it for the wonderful day! Be aware of a ~20 min uphill walk from the bus to lunch. One of the best parts of this day was the guided walking tour of Siena - Isabella our guide did an amazing job! The Chianti wine tasting was good too, with meat, cheese, bread and wine. Overall, highly recommend this tour!!

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April 27, 2022

The towns are spectacular. It's a beautiful area, well worth seeing. The visit was a bit rushed, but if you want a convenient arrangement, where you don't have to worry about planning your trip, driving, finding a parking a spot etc., it's a good option. The driver Eddy was nice, spoke many language and also acted a bit as a guide during the drive. The only suggestion I have is advising the customers in advance that having lunch in Siena might be tricky when there are a lot of tourists around. It took us almost an hour to find seating and to be able to eat a prepackaged sandwich at a small cafe. Everything everywhere seemed all booked up. But otherwise, this day trip was the highlight of our weekend and we recommend it.

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November 2, 2021

Incredible tour with fantastic staff. Anastasia, Orlando, and Fabiano were so kind and attentive. I had my 3 year old daughter with me and she was welcomed by the group, and felt very comfortable. I forgot something in the bus at the end of the tour and the whole team went out of their way to arrange for me to get my belongings back. They could've said it's not possible, but instead, they made it happen! Truly grateful to the staff and this tour was one of my favorite activities in our 10-day trip to Italy. Would book with them again, and highly recommend them!

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October 17, 2021

Product ID: 7679