Private Excursion to Siena, San Gimignano and Chianti Landscapes

Badge of ExcellenceFlorence, Italy
Likely to Sell Out

From $475.23

Price varies by group size

Select Date and Travelers

Free cancellation
Up to 24 hours in advance.
  • 8 hours (approx.)
  • Hotel pickup offered
  • Mobile ticket
  • Offered in: English


Explore the Chianti countryside on this full-day private tour of Siena and San Gimignano. Departing from Florence, head first to Siena for a walking tour of the city’s medieval streets. Admire the palaces and Piazza del Campo, followed by time to explore independently. Then travel via the fortified village of Monteriggioni to the town of San Gimignano and discover the medieval architecture and art on your own. Afterward, reunite with your private driver to travel back to Florence.
  • Full-day private tour from Florence to Siena and San Gimignano
  • Discover the towers and frescoes of San Gimignano
  • Have free time for lunch and to explore in Siena
  • Professional private guide in Siena

What's Included

  • Pick up and drop off at your Hotel if centrally located in Florence
  • Transport by deluxe air-conditioned vehicle with WIFI on board
  • English/Italian speaking driver
  • Local professional Guide at your side in Siena
  • Gratuities
  • Guide Service in San Gimignano
  • Entrance fees to the Cathedral in Siena
  • Everything not mentioned as Included

Meeting And Pickup

Pickup points

Select a pickup point

Start time

09:00 AM

Pickup details

Pick up at 9 am at the Hotel in Florence, if centrally located (indicate the name of the Hotel) In case the Hotel is not located in Florence city center we will arrange the pick up in a location in Florence city center to be advised.

What To Expect

After being picked up from your hotel in Florence, your private driver will take you first to the medieval city of Siena. Begin with a private tour of this wonderful city starting from Piazza del Campo, the famed site of the Palio di Siena, the horse races held  twice a year. Afterward, soak up some free time to continue exploring independently or to purchase lunch.

Along the way, take in the scenic countryside of Chianti, and see the village of Monteriggioni, whose medieval walled fortifications still remain intact.

From there, travel to the walled medieval city of San Gimignano. Resting on the top of a hill, explore the area’s impressive Romanesque and Gothic architecture, frescoes, towers and more.

After, hop back in the car and begin the return trip to Florence.

If you would like any special interests (architecture, history, art) highlighted in your private tour, please list them at the time of booking so that your local guide in Siena can accommodate you.

Piazza del Campo

Meet your private driver at your hotel for a beautiful excursion through the delightful hills of the Chianti countryside,with an ever-changing scenery of vineyards and olive trees. Upon arrival in Siena, your guide will bring you on a private tour of the old city centre: walking along the small medieval streets, admiring the splendid palaces and Piazza del Campo, one of the most beautiful in the world, where you will find the Palazzo del Comune(exterior). Free time for lunch (not included).

4 hours Admission Ticket Not Included

Torre del Mangia (Pass By)

a symbol of Piazza del Campo and one of the highest towers in Italy

Additional Info

  • Confirmation will be received at time of booking
  • Not wheelchair accessible
  • Most travelers can participate
  • This is a private tour/activity. Only your group will participate
Operated by CAF Tour and Travel

Cancellation Policy

You can cancel up to 24 hours in advance of the experience for a full refund.

  • For a full refund, you must cancel at least 24 hours before the experience’s start time.
  • If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.
  • Any changes made less than 24 hours before the experience’s start time will not be accepted.
  • Cut-off times are based on the experience’s local time.
22 reviews
Total review count and overall rating based on Viator and Tripadvisor reviews
Reviews by Viator travelers.
Showing 1-10 of 22 reviews
Great Excursion
Michael_H, Feb 2020
Driver was fun. Good sense of humor; Can't recall his name (he is a Brit who relocated to Italy.) Siena was nice, San Gimignano and Montefrigironi (sp) were terrific. Great trip; great value.
Response from Host, Mar 2020
Dear Michael_H, let us thank you for having joined our of our private tours and having shared your experience with us and our common readers. We are so glad to hear that you have appreciated so much your Private Excursion to Siena, San Gimignano and Chianti Landscapes. See of having been able to let you live exactly the kind of experience that we want all our customers to live, represents the best reward for all the efforts and passion that we daily put in our job. We hope to welcome you soon again in another of our activities. Our Best Regards
Siena and San Gimignano Tour Outstanding
Michael_M, May 2019
Great Driver for the day (Paul) who was super informative and put together a great to a local winery at lunch. Our guide in Siena (Maria) was very well informed and did a great job showing us the city and explaining all of its treasures.
Response from Host, Jun 2019
Dear Passenger28688744083, first of all we want to thank you for having joined one of our Tours! You can't imagine how proud and happy we are reading your review! We started our activity in 1954 and we always do our best to leave a memorable experience in our customers. We thank you so much for sharing your experience with us and hope to meet you again in the future! Our Best Regards
The guide in Siena was great and the...
Kathy C, Jul 2017
The guide in Siena was great and the tour was informative. I would plan ahead for a wine tasting, too. We were able to fit one in at the spur of the moment but we ran over time and were charged an additional 70E for the time. The driver was very nice and eager to please but his English wasn't great.
This was an excellent experience. We...
Patrick D, Jun 2017
This was an excellent experience. We liked the private walking tour of Sienna very much. We were able to add in a visit to a winery with lunch and tasting. This was arranged by our driver at the last moment at the begining of the day.
Nicola was an excellent guide...
Colin D, Oct 2015
Nicola was an excellent guide. Informative, funny and engaging company.
Our tour guide we met in Siena was...
Janice Murphy, Oct 2015
Our tour guide we met in Siena was wonderful. She had lots of interesting stories and it was really relaxed. The driver was very nice but probably could increase his knowledge so that he could point out interesting things during the trip. San Gimignano - it was too short and without a guide we were a bit lost as to what we could do. It was really busy too.
The guide in Siena was very...
marjolaine d, Oct 2015
The guide in Siena was very knowledgable, it was a pleasure to visit this beautiful city with her.
We had a wonderful time touring...
Vita Marie M, Jul 2015
We had a wonderful time touring beautiful Siena and San Gimignano with our incredible driver, Roberto, in his luxurious Mercedes SUV. Roberto was prompt and professional, but warm, informative, funny and gracious too. We chose a private tour so my mother, who has difficulty walking, could really enjoy some sightseeing and this worked out beautifully. In Siena, we were met my Monica who gave us a comprehensive tour of the city and magnificent Duomo. Roberto called ahead for lunch reservations at the Bel Soggiorno in San Gimignano, and we had a delicious meal with an unforgettable view. We had enough time to then explore the city on our own. On our return, Roberto made a special side trip so that we could pay our respects at the US military cemetery located outside of Florence. A great experience and absolutely worth the price.
Our guide was wonderful, full of...
Diane R, Sep 2014
Our guide was wonderful, full of information and anecdotes and went out of his way to show us the wonderful countryside and made some detour to show us some of his favorites spots. The guide who took over for the Siena visit was extremely knowledgeable and interesting, we learned a lot about the history of this beautiful city.
We fell in love with Siena! Felt so...
Joyce S, Jul 2014
We fell in love with Siena! Felt so at home - and at peace - walking through the city. It presented us a wonderful mix of history, local color, and beautiful scenery! Our guide was knowledgeable - but did not overwhelm us with facts and details - very accommodating to our needs. One of the pearls of the vacation,
Terrific. The private guides make...
Marianne P, May 2014
Terrific. The private guides make it more special and gives flexibility to spend more or less time in a shop or two.
Great tour with Marzio. He picked us...
ellen a, Jan 2014
Great tour with Marzio. He picked us up at our hotel and off we were on a fun and informative adventure. We left Florence for Siena and San Gimignano, with a stop for wine, olive oil and balsamic vinegar tasting at Tenuta Torciano. Wonderful wines and food. Siena tour guide was tremendous - a great city to spend a bit of time in. San Gimignano would have been great to spend a little more time in, but most shops were closed (mid-week Early December) Would highly recommend aviator Tours.
This was an amazing day for our...
Mary S, Jun 2013
This was an amazing day for our family. Our driver was wonderful and our tour guide in Sienna was a local woman who was extraordinary. Her personal connection to the city was the perfect touch. We never felt rushed or inconvenienced. It seemed a bit pricey when we booked it but was worth every penny
Even the rainy day did not take away...
Donna P, Jun 2013
Even the rainy day did not take away from our tour. Barbara in Siena was great! Her being a native of Siena was such a plus on the tour. We got see parts of Siena we would not have seen or learned about on our own. At the end she was able to get us into the Duoma for Mass with no hassle. We were not able to spend enough in San Gimignano and the rain did not help. It will be a definite go to next time we go to Italy.
All went off without a hitch! We...
Elaine A, Jun 2013
All went off without a hitch! We were picked up from our hotel just before 9.00. Our driver was extremely curteous. He gave us the impression that nothing would be too much trouble, and, upon our request, took us to Montregionale for a lovely lunch. Our guide in Siena was just brilliant! Being local, she had so much info. to impart, with the odd entertaining anecdote along the way. Full marks, Viator!
Siena and San Gimignano are lovely...
Mandie T, May 2011
Siena and San Gimignano are lovely towns and could not be missed. Our tour guide at Siena is also informative and nice! However, the private tour is pricey because lunch is not included and there is no private tour guide at San Gimignano. The driver also gives us only 1.30 hrs in San Gimignano which is not enough.
Loved it!! Great driver - great Siena...
Lynn O, Apr 2008
Loved it!! Great driver - great Siena tour guide - great restaurant in San Gimignano - all around fantastic!!! Not to be missed. GREAT EXPERIENCE - BEAUTIFUL!!!
We did a private tour and the guide was...
Anthony C, Sep 2007
We did a private tour and the guide was wonderful. The day was well worth every penny.
Gute Anfahrt aus Florenz mit...
Peter R, Feb 2016
Gute Anfahrt aus Florenz mit Limousine inkl. Chauffeur englischsprechend. Ausgezeichnete Führung mit außergewöhnlich gut deutschsprechendem Guide. Sehr kompetent. Wunderbar.
Journée très bien organisée;Horaires...
Albert C, Apr 2013
Journée très bien organisée;Horaires respectés;chauffeur très agréable;la guide à Sienne très compétente. La ville de Sienne est chargée d'Histoire ;les explications d'une guide nous ont permis d'apprécier cette belle ville .Le temps libre était suffisant avant de reprendre la route pour le joli village médiéval de San Gimignano.