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San Gimignano, Siena, Chianti Day Trip
Activities in Florence

San Gimignano, Siena, Chianti Day Trip

1,174 reviews
Excellent guides. A great trip!
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10 Anonymous
  • English
  • 11 hours
  • Hotel pick up

Set off on a fabulous day-trip from Florence and discover Siena, Tuscany’s medieval town, visit Monteriggioni with its fascinating landscape, followed by San Gimignano, famous for its white wine and then go on a wine tasting in the Chianti region.  


In the morning, your host will collect you at your hotel on an air-conditioned coach and drive you through the Chianti hills, stopping at San Gimignano, a small walled village founded in the Middle Ages. It is only 60 kilometres from Florence.

Explore at your own pace San Gimignano, known as the Town of Fine Towers, for one hour and 15 minutes and find out why it was declared a UNESCO World Heritage site in 1990. The town is renowned for its tower houses, which were built by the wealthy families of San Gimignano as a sign of their power and affluence. You’ll have free time to visit the city and its 14-still standing towers.

The day tour continues with a guided tour of Siena, only 30 minutes’ drive away. Follow your tour guide through the narrow streets and learn all about the town’s impressive history. Step into the Siena Cathedral, a Gothic masterpiece packed with remarkable artwork by Michelangelo and Donatello. Explore Piazza del Campo that houses the impressive Palazzo Pubblico and find out about the Palio di Siena, the city’s renowned horse race.

After the guided tour, you will enjoy a light lunch in the area and try the delicious local gastronomy. You will also revel in a tasting of various types of ice-creams from a local ice-cream maker (not included).

In the afternoon, cross the Chianti region, an area full of vineyards and wine cellars where the famous Chianti wine is produced. The striking landscapes of Chianti are the most characteristic of Tuscany.

In Chianti, you will stop at Monteriggioni, one of the regions most emblematic towns with its still intact city walls. Then, before heading back to Florence you will stop at a famous wine cellar, where you will not only do a wine tasting, but also have some exquisite cold meats typical of the region and taste true olive oil. The tour lasts around one hour. 

The tour will come to an end in Florence at 7:30 pm.

Order of the tour

Please note that the itinerary can change and that the visit to the wine cellar can take place in the morning.

Hotel Pick-Up

  • This tour includes a pick-up option from most centrally-located hotels (not apartments) in Florence. When you book the tour, please give us the address of your hotel. If you're staying in the outskirts or near Santa Maria Novella train station, your host will be waiting for you at the arranged meeting point.
  • Pick up will be approximately 30 minutes before the tour is due to begin. Once you have made your reservation, we'll contact you with an exact time.


Adults Children 4-12 years old Children under 4
US$ 73.5
US$ 37
  • Adults

    US$ 73.5
  • Children 4-12 years old

    US$ 37
  • Children under 4


More information


11 hours

Language English

The tour includes an English speaking guide, but the tour can sometimes be carried out in two languages.


Hotel pick up.

Return transportation by air conditioned coach.

English speaking host will accompany you during the excursion.

English speaking guided tour of Siena.

Entry to Siena Cathedral.

Visit a wine estate with a wine tasting and sampling of other traditional products.

Not included

Ice cream tasting.

San Gimignano and Monteriggioni guided tour.

Return transfer to your hotel.

When to book?

Book as soon as possible to guarantee availability, especially during public holidays and festivities.

You can book up until the previous day (12:00 local time) if there are still places available.


Once your booking has been confirmed, you will receive an email containing your booking voucher. Please print it out or download on your smartphone/tablet to show on the day of the activity.

Frequently asked questions

  • Q - How to book?

    A - To reserve the activity, choose the date and complete the form on this page. You will receive your confirmation immediately.

If you still have more questions, check out our section on frequently asked questions. If you need help to book an activity or have any enquiries, please contact us.


No (not suitable for people with reduced mobility).

US$ 73.5
No hidden fees or surcharges


Free! Free cancellation up to 48 hours before the activity starts. If you cancel under this time or do not show up, you will not be refunded.

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