Day trip

From Florence: Siena, San Gimignano & Monteriggioni Tour

From Florence: Siena, San Gimignano & Monteriggioni Tour

Likely to sell out

From US$ 52.78 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. Arrive at 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 landscape. Make the second stop at Siena. Explore the Piazza del Campo, famous for the Palio Horse Race and for its splendid examples of Gothic civic architecture. You can also visit the magnificent Palazzo Pubblico.

Finally, visit Monteriggioni and its intact medieval city walls. Then, 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
    Customer reviews

    Overall rating

    4.4 /5

    based on 833 reviews

    Review summary

    • Guide
    • Transportation
    • Value for money
    • Safety

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    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

    Full day to visit Siena, Monteriggioni and San Gimignano. The tour guide was not the best however he shared the basic info about the places we visited. The wine tasting is nothing special. We specifically didn’t like the wines we tasted but this is based on the personal taste. Overall it was a shame we visited San Gimignano last and it was almost dark so we didn’t get enough to enjoy the area.

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    November 16, 2022

    Jacob was a great guide, and the rest of the team as well. Very well organized for a large multilingual group. Some parts are a bit rushed but that is expected given the number of sites being visited. Wine was nice but the vineyard visit wasn't too informative. Overall a fun day trip.

    October 15, 2022

    Product ID: 17166