Day trip

From Florence: Siena, San Gimignano & Monteriggioni Tour

Day trip

From Florence: Siena, San Gimignano & Monteriggioni Tour

Likely to sell out

From US$ 59.77 per person

Likely to sell out

Enjoy an unforgettable day in Tuscany with delicious local wines. Visit the charming medieval towns of Siena, San Gimignano and Monteriggioni. Discover the beauty of Chianti's landscape.

About this activity

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


  • Visit San Gimignano, a UNESCO World Heritage Site
  • Discover the views in Monteriggioni, a dazzling hilltop town
  • Wine tasting is provided in a farmhouse located in the heart of Chianti
Full description

Experience the charm of Tuscany on a day trip to Siena, San Gimignano, and Monteriggioni from Florence. Try a variety of Chianti wines paired with snacks and admire the picturesque Tuscan hills. 

Cross the beautiful Chianti hills as you ride south from Florence in an air-conditioned GT bus. The first stop is at Monteriggioni, a medieval hilltop town that is famous for its intact medieval city walls. After some free time, head to the world famous Siena.

Explore the Piazza del Campo, that is known for the Palio Horse Race and for its splendid examples of Gothic civic architecture. Have time to visit the magnificent Palazzo Pubblico. 

Arrive in San Gimignano, a medieval town declared a World Heritage Site by UNESCO. Take time to wind your way through the narrow streets and admire the lush landscape.

Finally, head to the Chianti area and enjoy postcard-perfect landscapes. Conclude your day at a famous wine estate and taste fine Chianti red wine along with homemade snacks.

  • Round-trip transportation in air-conditioned bus
  • Free time in Siena, San Gimignano, and Monteriggioni
  • Visit to a wine cellar
  • Wine tasting
  • Oil and balsamic vinegar tasting
  • Snack
  • A guided tour of Siena (if option selected)
    Not suitable for
    • Wheelchair users

    Select participants and date



    Meeting point

    The meeting point is at Piazza Montelungo which is located 5 to 10-minutes from Santa Maria Novella Train Station by foot. Look for a staff member wearing a fuchsia Ciaoflorence jacket and holding a Ciaoflorence clipboard.

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    Important information

    What to bring

    • Comfortable shoes

    Not allowed

    • Pets
    • Luggage or large bags

    Know before you go

    • This tour is conducted in multiple languages at the same time
    • English and Spanish languages are always guaranteed; a minimum of 4 pax is required for French, German, Italian or Portuguese
    • Please note that semi-independent options do not include lunch and the Siena guided tour
    • The order of the towns visited on the route is subject to change
    Customer reviews

    Overall rating

    4.4 /5

    based on 872 reviews

    Review summary

    • Guide
    • Transportation
    • Service
    • Organization

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    The tour covered all the major points as advertised. I was on a coach with an English speaking guide, who did a great job keeping everyone on track throughout a busy day. It was a very busy day, and while I chose the tour specifically because it visited the three towns, I personally feel there would be more value to visiting just two towns and removing the wine tasting. We arrived in Monteriggioni so early that the walk on the walls wasn't yet open. I didn't do the tour in Siena, so can't comment. I would have liked to climb the bell tower there, but that was sold out, having an option to have that booked in advance would have been nice. Wine tasting was unnecessary, time could have been better spent between Soena and San Gimignano, where we arrived at twilight, which was beautiful, but meant that most attractions were closing up by the time we arrived. It was a great way to get to all the towns in one day, but in my opinion, ultimately too much.

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    January 10, 2023

    The tour was really excellent. Great tour of Siena and San Gimignano, two of the best places in Italy, wine tasting and a stop at another picturesque village. Excellent guides and driver. A must experience in Tuscany and a truly value for money. Thank you guys!

    January 3, 2023

    Fantastic places to go see and much better than trying to jam Pisa in like other experiences. We didn’t think the hour at a wine tasting spot was worth it because at least 10 of us didn’t drink alcohol. (There’s no option to skip it and they don’t give you a tour, instead you stand in a room with people trying wines). We didn’t do the audio guide and are glad we didn’t because we had the free Rick Steves Siena Walking tour on our phone so we walked around without a large group. This is not a small group tour, but rather a multilingual transport from Florence to Monteriggioni (25 minute stop), Siena (about 2.5 hours for lunch), wine tasting spot (1 hour), then lastly San Gimignano (1 hour or so) on a large bus. It wasn’t too bad since each place we stopped did not have any other busses or many tourists (being the off season/end of November). It did get dark just after we arrived in San Gimignano. Overall, would do it again but there should be something for non-alcohol drinkers to do.

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    December 7, 2022

    Product ID: 17166