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

From US$ 50.94 per person

Likely to sell out

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
Reserve now & pay later
Keep your travel plans flexible—book your spot and pay nothing today.
Covid-19 precautions
Special health and safety measures apply. Learn more
Duration 11 hours
Check availability to see starting times.
Live tour guide
Spanish, English, Italian, Portuguese, French

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 stop (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
  • Credit card
  • Comfortable clothes
  • Packed lunch
  • Cash

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 3037 reviews

Review summary

  • Guide
  • Transportation
  • Value for money
  • Safety

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We did the tour in July, our guide was Ana. She was very nice. First we visited Siena, we did a guided tour of the city in Spanish and then we had free time to eat. the stop in this city was a bit short for us. ( 3 hours). Although the tour gave the option to include food, we preferred to eat a pizza on the street and have time to see the cathedral from the inside, which is very worthwhile. We then made a stop in lornano for wine tasting. The visit to the wineries was in English (we were only 4 Spaniards) but we understood everything quite well, the wine was very tasty and so was the olive oil. Then we made a 30-minute stop in Monteriggiori, which is a very small town, and we had time to see it. Finally we stopped in San Gimignano (hour and a half) and on the recommendation of our guide Ana we tried some delicious ice creams (dondoli) and we visited the city quietly. In general I think the tour is great

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July 21, 2022

Loved this tour, it’s setup so that the guide gives you a little history about the area you’re going to visit next followed by open time to explore the places at your own pace. When getting on the bus, pick a place in the back seats. You’ll probably have more open seats around you so that you can direct more air fans your way! (We did our tour in July when temps were hot hot HOT, AC in EU can’t go as cold as quickly as US so be prepared to sweat a little. Handkerchiefs, water, hand fans, and hat/sunglasses are key items for keeping cool). I chose this tour specifically because I love the Assassin’s Creed games and always wanted to visit the actual Monteriggioni. This delivered and then some!

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July 6, 2022

The trip was very nice, but a little rushed. If there was a bit more time in Siena would have been better. In our opinion, we could have skipped Monterrigioni for more time in Siena (the castle is nice, but we went there in the hottest past of the day and it was impossible to walk the walls and feel ok). Our guides Yuliya and Manuel were very friendly and approachable. Our kids loved Yuliya.

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June 27, 2022

Product ID: 7679