From Florence: San Gimignano, Siena and Chianti Wine Tour
4.4
761 Ratings
Metropolitan City of Florence

Embark on a full-day wine experience in San Gimignano, Siena, and Monteriggioni. Explore Tuscan villages, indulge in wine tastings, and immerse yourself in the beauty of the Chianti wine region.

Duration: 11 hours, 15 minutes
Cancellation: 1 day learn more
Highlights
  • Historic Centre of San Gimignano - Enjoy some leisure time in this breathtaking medieval village, recognized as a UNESCO World Heritage site for its beauty and iconic tower houses. Known as the “Manhattan of the Middle Ages,” San Gimignano offers you the freedom to explore its many attractions, including tasting world-renowned ice cream at Gelateria Dondoli.
  • Porta San Giovanni - This is one of the gates leading into the medieval village.
  • Collegiata di Santa Maria Assunta - Duomo di San Gimignano - During your free time, consider visiting the stunning Duomo located in the village’s main square. This site is a remarkable example of a well-preserved medieval town, complete with original ancient walls, which is a key reason for its UNESCO World Heritage status.
  • Palazzo Pubblico e Torre Grossa - For a journey back to the Middle Ages, climb this original tower house. The view from the top is breathtaking, offering a unique skyline of towers. Many of San Gimignano’s towers were built in the 14th century by families showcasing their rising power.
  • Piazza della Cisterna - One of the village’s main squares, named for the well at its center. Admire the beautiful palaces surrounding the square. The old town center is filled with charming alleys, squares, museums, palaces, churches, magnificent towers, and artisan workshops.
  • Monteriggioni - The tour continues with a visit to the splendid Monteriggioni castle, a well-preserved medieval fortress. You might recognize it from the Assassin’s Creed video game series.
  • Fortezza Medicea - Marvel at this ancient fortress located just outside Siena’s center.
  • Centro Storico di Siena - Spend your afternoon exploring Siena and its stunning historic center. Our official guides will lead you through the old city center, where you can admire the magnificent Siena Cathedral (Duomo) and the Town Hall in Piazza del Campo, the site of the world-famous Palio horse race.
  • Piazza Salimbeni - Begin your guided walking tour with a local guide here. Discover the city’s history and anecdotes on foot, appreciating its transformations over the centuries and enjoying spectacular landscapes and intriguing details.
  • Palazzo Tolomei - An ancient palace in the heart of Siena. Learn about the great noble families like the Piccolomini, Tolomei, and Salimbeni, their palaces, the Palio di Siena tradition, and the city’s pilgrimage and sanctity stories.
  • Via di Citta - One of the main roads in the historic center. Walk along it with your guide.
  • Piazza del Campo - The famous shell-shaped city center, a focal point for Siena’s civic and political life and the site of the Palio di Siena horse race, held twice a year. Ten horses representing the main districts race around the square in this renowned event.
  • Fonte Gaia - An ancient fountain adorned with white marble in Piazza del Campo. The fountain features wolves symbolizing the mother of Romulus and Remus, celebrating the link to ancient Rome. The original sculpted panels have been moved for preservation and can now be seen at Santa Maria della Scala.
  • Palazzo Pubblico and Museo Civico - Once the government seat of the Republic of Siena, this building now serves as one of the city’s town halls. It houses the Civic Museum of Siena, which features famous paintings and frescoes, including “The Maestà.”
  • Duomo di Siena - Siena’s Cathedral is one of Italy’s finest Gothic-Romanesque churches, with breathtaking beauty. The exterior features three portals, with the central one dominated by a bronze sun, and a facade of black and white marble, the city’s colors.
  • Facciatone - Admire this part of the Siena Cathedral, which also houses paintings and sculptures by Donatello, Pinturicchio, and Nicola Pisano.
What's Included
  • Expert tour leader
  • Wine tasting in a typical winery
  • Free time in Siena
  • Free time in San Gimignano
  • Free time in Monteriggioni
What's Not Included
  • Hotel pickup and drop-off
  • Gratuities
  • Lunch
Additional Information

Enjoy a full-day tour visiting Tuscan villages and exploring the Chianti wine region! The villages of San Gimignano and Monteriggioni, the Chianti area, and the medieval town of Siena are situated in the heart of Tuscany. Reach easily our meeting point by taking the T1.3 tram heading to Villa Costanza. Start your amazing journey in the first stop of Siena, the world-famous city of Palio horse-race in Piazza del Campo. Afterward, head to our beautiful winery nestled in the Chianti Area, with scenic views of the Tuscan countryside. Third stop, continue with a visit to the marvelous Monteriggioni castle, a medieval fortress that is really well preserved. You may also recognize it from the Assassin’s Creed video game series. Last but not least, explore San Gimignano, another magnificent example of a Medieval urban town where you will have free time to visit the village and its splendid squares and towers. At the end of the day, take your ride back to Florence.

  • A moderate amount of walking is involved.
  • Operates in all weather conditions, please dress appropriately
  • Entrance to the Siena Cathedral is not included, clients can enter at their own expenses and depending on Cathedral opening times. Please note that will not available on Sundays or Bank Holidays and during special event opening times can change
  • Please note that Portuguese option requires a minimum of 4 pax. Otherwise, the tour will be guaranteed in English.
Location
Florence (Villa Costanza)
Meet us at Villa Costanza, in front of 'The Florence Gate' Café. Reach the meeting point by T1 Leonardo tramway to Villa Costanza (get off at Villa Costanza stop which is the end of the line). The ride is 20 min from center and you can choose the nearest stop. Our staff will wear a green shirt.
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
4.4
(761 Ratings)
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Melanie_w
Jul 25, 2024
Trip was great and we... - Trip was great and we especially enjoyed our guide Lila. All of the towns are beautiful and the winery did an excellent job of presenting their products.
Review provided by Viator
Zoricaj706
Jul 8, 2024
Superb - Beautiful day splendid villages, beautiful Tuscan countryside. Chianti tasting very informative. Excursion not to be missed. Quality price at the top!
Review provided by Tripadvisor
Elizabeth_s
Jun 29, 2024
A visit to Tuscans must see and experience. - Free time to enjoy in Siena and San Gimignano. The guide Erica was friendly and shred lots of relevant information.
Review provided by Viator
Mary_g
Jun 23, 2024
Fabulous experience - Marta the tour guide was extremely well versed in her knowledge of the tour. She was very personable and nothing was too much trouble for her The countryside was absolutely stunning. The wine tasting was a lot of fun, the balsamic vinegar had an incredible taste. San Gimignano was breathtaking All in all a fabulous tour. Was sad for it to end.
Review provided by Viator
Caroline_t
May 19, 2024
Tuscany fun tour - This was a small group tour. I would recommend to purchase tickets for Siena sites ahead of time so that you save time and not stand in cues. The wine tasting and lunch at Poggio ai Laghi in Monterioggioni was so much fun and the views at San Gimignano were spectacular.
Review provided by Viator
Nadja_g
May 11, 2024
A wonderful day in south Tuscanny - Marco was a wonderful guide for the day in these 3 towns in Tuscanny, we enjoyed it very much! He showed us were to find the most important sighrs in each city, gave us some insider tips on where to eat or drink or enjoy sweet delights. Great tasting of wine, olive oil, aceto balsamico. Nice group size of just 15, new friends were made by the end of the day!
Review provided by Viator
Alexandra_m
May 5, 2024
INCREDIBLE! - This was an incredible experience for my husband and me. Marco was very nice, knowledgeable, upbeat, fun and friendly. What’s great about it is you visit these different areas and you are on your own for a good amount of time (1-2 hours) which is REALLY nice to just explore. Things to keep in mind: Be on time, it’s a LONG day (that is very clear given the duration stated on the tour when booking it), must wear your most comfortable shoes, be prepared to walk on very steep areas to fully explore the city given the allotted time, be cognizant of weather/climate since it will vary from city to city (we came in spring, the morning was very cold but in the afternoon it was very warm) and lastly, if you are prone to getting car sick, pack your meclizine! The driver was great, but roads were very windy. Would I do it again? Absolutely!!! We were prepared and ready for this wonderful experience!!!
Review provided by Viator
Mohammed_m
May 5, 2024
Exploring Tuscany in a fun way ! - Our tour guide Marco was a very friendly person, informative as well and always willing to help and gives recommendations. One of the best things that I would like to mention is for every place you go you have the time to discover it freely on your own pace there is always enough time. Great tour I loved it and I totaly recommend it !
Review provided by Viator
Wendy_e
Apr 20, 2024
Tuscany - Wine tasting. Visiting Tuscan cities. Enjoyed it all Very good tour guide. Would do it again. Very good tour for money.
Review provided by Viator
Anisa_k
Jun 5, 2024
Poor description / instructions - be wary! - Bad explanation in the description on meeting time vs departure time. Most of these tours write explicitly instructions and this one never said meet up time and departure time was the same. We left early from our hotel and accounted for some traffic but ran over by 10 mins. We called and informed the tour group we’ll be late. They said the bus departs at the meet up time and only waiting 5 mins. We got there and they claim to have waited for us but when we arrived at the location it wasn’t clear what to find the bus so we ended up missing it. We contacted Viator and if they suggested for us to meet at San Gimignano we would have by train and continued on but unfortunately they claimed their description says to arrive 20 mins earlier (which it does not)
Review provided by Viator
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up to 15 guests
1 Adult
September 2024
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