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See the Tuscan gems of San Gimignano, Siena, and Chianti on a day trip from Florence. Stop first in the city of Siena to visit a 'contrada' museum for some Sienese history. 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 in Chianti before returning to Florence.


  • Day trip to Siena, San Gimignano and Monteriggioni from Florence, led by a professional tour escort
  • Travel through the Chianti countryside in Tuscany
  • Explore Siena's Old Town with your guide
  • Explore one of Siena's contrade museums
  • Discover the famous Siena Cathedral and its treasures
  • Make a stop in a charming village in Chianti

What You Can Expect

Siena with Palio’s Contrada, San Gimignano and Chianti, Day Trip from Florence with Wines and Food Tasting

San Gimignano

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. 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 to sample fine local wines, accompanied by snacks.

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

Please note that the order of the visits may change.


Customer Reviews


5 star rating: Highly Recommended September 2018

Great trip from Florence to see some nearby cities and great sites! Siena and wine tasting were the highlight!

Kristin J

5 star rating: Highly Recommended August 2018

AMAZING!!! great tour guides especially in Siena! one of the highlights in our italy trip!

Pamela M

5 star rating: Highly Recommended July 2018

An excellent day, well run. Visited 4 places that were all amazing. The highlight was the enthusiasm with which our guide exhibited at the wine tasting.


5 star rating: Highly Recommended July 2018

This is a great tour. Siena is an old and beautiful city well worth seeing. The Chianti trip is so much fun. Great wine and food. We highly recommend this tour.

Caroline P

5 star rating: Highly Recommended June 2018

This was a fun tour, but keep in mind there is a LOT of walking...! Local tour of Siena was outstanding and very informative. Wine tasting was excellent and very well done. Pick up location is quite difficult to find...nowhere to sit..

Kerry EW Australia

5 star rating: Highly Recommended June 2018

Excellent tour. Really well organised and the guides were fabulous. The Siena guide who explained the Contrada and the Palio was wonderful. I would have loved a little longer in San Gimignano. In Siena we also took the tour of the Cathedral spectacular but then we had no time to do any shopping but I guess you cant have everything. We had a fabulous day even though it was quite long. My only small criticism would be better instructions for finding the tour start point. There were lots of renovations at the train station so it was a bit of a challenge finding the bus stop.


5 star rating: Highly Recommended April 2018

Very well organized tour, special thanks to our professional guide Tiziana!

Richard A

5 star rating: Highly Recommended April 2018

Great trip and good value for the price of the tour. Four stops all good. Obviously, when your making four stop you don't have as much time to explore as you want at each place but I'm glad we took this tour instead of one that just covers Siena. Be prepared for 11 hour day.....8:30 AM to 7:30 PM. Enjoy!!!


5 star rating: Highly Recommended April 2018

Siena is one of my favorite towns. We loved the tour and our guide

Siok Lan P

5 star rating: Highly Recommended April 2018

Definitely value for money...very worthwhile trip...covered quite a fair bit with enough free time to roam around .

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