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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

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

Jimmy Ray P

5 star rating: Highly Recommended November 2016

Outstanding trip of these two amazing cities. If your in Florence, don't pass this one up!

Kathleen W

5 star rating: Highly Recommended November 2016

Thoroughly enjoyed this trip. Our local guide in San Gimignana Paul was very knowledgeable and entertaining. All stops were well worth the time and gave us a different aspect to this area. Would recommend this trip.

Catherine F

5 star rating: Highly Recommended November 2016

This was a wonderful day trip that took us through beautiful Tuscan countryside. Our very knowledgeable tour guide on our bus trip out pointed out sights as we moved out of Florence into the Tuscan countryside and shared history and traditions involving the Florence/Siena rivalry and history. Our first stop was the medieval hilltop town of San Gimignano, and I do mean hilltop. We enjoyed exploring the beautiful medieval town on our own -- the shops, the church, as well as a delightful opportunity to enjoy a cafe and delicious pastry on the square. Siena, was our next stop where after some free time and we met up with a very informative local guide who shared Siena's history, including the district horse racing extraganza, she took us to visit a contrada museum, churches, and much more. Greve in Chianti was next and finally a wine tasting at a private local winery as the sun was setting before boarding the bus to return to Florence. All in all a very worthwhile trip.

Richard M

5 star rating: Highly Recommended November 2016

Excellent trip and excellent tour guide,whose name escapes me at this moment. Thoroughly enjoyable

Trent S

5 star rating: Highly Recommended October 2016

This was an excellent tour. The guide in Siena was so knowledgeable and entertaining. She was well organized with her stories following the flow of our path through the city. Both Siena and San Gimignano were incredible to see and would be difficult to do as a day trip on your own using the bus and train. We know, we looked. I was thinking that it might be too much to try to add Greve in as well for the wine tasting, but I was wrong. It was a great addition to the trip. We were so glad that we ended up doing this tour. On our next visit to Italy we are going to try to stay in Siena and Greve for a few days. It was love at first sight with regards to these two cities in Toscana! Ciao!

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