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See the Tuscan gems of San Gimignano, Siena, and Greve in Chianti on a day trip from Florence. Stop first in the city of Siena to visit a 'contrada' museum for some Sienese history, as well as the Basilica di San Domenico for an interior tour. Afterward, explore the medieval hilltop town of San Gimignano and enjoy a tasting of local blends at a nearby winery. Top off your trip at the village of Greve in Chianti before returning to Florence.


  • Day trip to Siena and San Gimignano from Florence, led by a guide
  • Travel through the Chianti countryside in Tuscany
  • Visit inside the Basilica of San Domenico in Siena
  • Explore Siena's Old Town with your guide
  • Explore one of Siena's contrade museums
  • Make a stop in the charming village of Greve in Chianti

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What You Can Expect

Siena, San Gimignano, and Greve in Chianti Day Trip from Florence with Wine Tasting

Admire the beautiful Siena Duomo

Depart from central Florence (near Santa Maria Novella train station) and ride south through the Tuscan countryside by coach.

After a scenic drive past the vineyards, arrive in Siena, heading first to the Basilica of San Domenico. Admire the Renaissance artwork inside with your guide before taking off on a walking tour. Take note of the uniquely striped marble of the Siena Cathedral and then enter one of the city's contrada museums.

Learn the history behind the contrades, or districts, of the city as you wander the exhibits. Hear about the individual traditions of each still celebrated today during the famous Palio horse race, which takes place in the main square twice a year. Afterward, take a brief break to purchase lunch.

Continue to San Gimignano, a medieval hill town best known for its impressive towers and frescoes. Soak up some free time to explore its streets independently before traveling to a small winery in the Chianti hillside. Walk in the vineyards, visit the barrel room, and sample four local wines, accompanied by snacks.

Top off your trip with a visit to the charming village of Greve in Chianti to peruse the local shops and main square. Your trip will conclude with transportation back to Florence.

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Customer Reviews

Peng Swee Y

5 star rating: Highly Recommended February 2017

Awesome tour. Our guide was very informative and helpful. In Siena, the guide was local, she knew every single histories and explained to us in details. Highly recommended.

Glinda United States of ... 

5 star rating: Highly Recommended February 2017

Great tour with a knowledgeable guide who shared information about each site visited as well as local insider info. In Siena the guide was a local who knew the history and city. I would definitely recommend this tour. My only caveat would be that Greve is at the end of a long day and really not a highlight. At that point I was ready to head back to Florence


5 star rating: Highly Recommended February 2017

Our guide is very informative and we enjoyed the day tour very much! All three places are beautiful and scenic. We prefer more time in San Gimignano as there are so much to see and shop. The wine tasting in Chianti was ok only.


5 star rating: Highly Recommended February 2017

Me encanto este tour, el guía muy bien, se implicaba esplicar la historia, curiosidades, en cada sitio que hemos visitado. La cata de vinos y productos típicos de región particular,como vista guiada de Siena. Se lo recomiendo. Por lo menos para mi era experiencia inolvidable.

Lizabeth M

5 star rating: Highly Recommended January 2017

Wonderful day trip from Florence! Especially loved learning about the Siena contrade and spotting their mascots around the neighborhoods.

francoise r

5 star rating: Highly Recommended January 2017

This was such a long day out. First stop to San Gimignano was brief but nice to see this little village with beautiful views. Then off to Siena. Our guide was amazing, the town is full of traditions and beautiful little streets wish i could go back again and we had a lovely lunch not included in the price so you go off on your own for 1 hour. Then on our way back to Florence we stopped at a vineyard... again beautiful views and friendly people but we did not like the wine testing but that's our personal taste! We felt a bit pressured to buy a few bottles which we did not but felt uncomfortable about it. It was nice but as the day was so long we wished we would have not got to the vineyard. Overall a fab day out with beautiful sceneries of Tuscani. Coach was clean and comfortable and the guide tried hard


5 star rating: Highly Recommended January 2017

Our guide was amazing. We learned a lot about the wines and history of the region. The tour was very informative and picturesque.

Nancy E

5 star rating: Highly Recommended January 2017

Everything was well planned and times along the tour were just perfect! I now have an idea of each place and would definitely will go back to each city and spend more time.


5 star rating: Highly Recommended December 2016

Nice day spent. our tour guide Matteo was amazing.

Thank you


5 star rating: Highly Recommended November 2016

Great tour guide, wonderful sites, highly recommend

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