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Explore the Chianti countryside on this full-day private tour of Siena and San Gimignano. Departing from Florence, head first to Siena for a guided tour of the city’s exquisite Cathedral and the Piazza del Campo, followed by some time to explore independently. Then travel to the charming town of San Gimignano and discover the medieval architecture and art on your own. Afterward, reunite with your guide 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 in Siena
  • English-speaking guide can create the best tour based on your interests
  • Professional private guide in Siena

What You Can Expect

Private Tour: Siena and San Gimignano

Visit the Cathedral of Siena

After being picked up from your hotel in Florence, your guide will take you first to the medieval city of Siena. Begin with a private tour of the Siena Cathedral, admiring the unique marble stripes of its interior as well as the Piccolomini Library, which hosts illuminated choir books and frescoes. Your tour will continue to the 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.

Reunite with your driver and 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. Along the way, take in the scenic countryside of Monteriggioni.

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 guide can accommodate you.

Customer Reviews

Karlene B

5 star rating: Highly Recommended March 2016

Good driver. Good guide.

marjolaine d

5 star rating: Highly Recommended October 2015

The guide in Siena was very knowledgable, it was a pleasure to visit this beautiful city with her.

Vita Marie M

5 star rating: Highly Recommended July 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.

Diane R

5 star rating: Highly Recommended September 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.

Joyce S

5 star rating: Highly Recommended July 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,

Marianne P

5 star rating: Highly Recommended May 2014

Terrific. The private guides make it more special and gives flexibility to spend more or less time in a shop or two.

ellen a

5 star rating: Highly Recommended January 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.

Mary S

5 star rating: Highly Recommended July 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

Donna P

5 star rating: Highly Recommended July 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.

Elaine A

5 star rating: Highly Recommended July 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!

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