Private Guided Tour: Siena, San Gimignano and Chianti Day Trip from Florence

These towns can’t be missed. We had the pleasure of spending the day with Giacomo. His strong English skills allowed for great conversation. He is deeply knowledgeable about the history of Italy and Tuscany. He was kind enough to make a small detour to the American cemetery outside of Florence, and a small monastery near San Gimignano that were deeply moving. Lunch was at a beautiful winery, Terre Di Sovernaja, overlooking the Tuscan hills. The food was simple and so delicious, complimented perfectly with their wine. We explored San Gimignano on our own and Giacomo guided us through Siena with a stop for a quick espresso at an off the path cafe. His warmth and deep knowledge made for a memorable experience overall.

I have lived in Italy for nearly 20 years and whenever I have friends or family visiting, I book Massimo as our driver. Some of my most memorable experiences in Italy have been out on an excursion with Chianti Drivers! This April, Massimo picked us up in Florence and took us to San Gimignano and Monteriggioni for time to explore on our own. Next, we headed to an exquisite winery for lunch and a cellar tour, before heading to Siena. Massimo is always exceedingly professional, punctual and polite. I cannot recommend this company enough!

Simone was wonderful. He was prompt, flexible and had a lot of interesting information to share. Our guide in Siena was very knowledgeable.

Great info provided by Massimo along the way. Viviana gave a tour of Siena. Wine tasting at Emma’s winery was superb!

We had an absolutely fantastic time. Two couples visiting from the United States. Simone, our driver, could not have been better. His knowledge was excellent. He took us on back roads and pointed out so many things we never would’ve gotten to see otherwise. The visit to Casa Emma Winery was above par and the food was excellent. The wine was quite tasty and the winery was absolutely beautiful. We highly recommend this company for a tour.

Highly highly recommend booking this tour! My family and I were celebrating my mom's 50th birthday in Italy and we booked the private day tour with our driver Simone. Not only did he show us the beautiful hidden sights of Tuscany, but he was also a very kind and fun guy to spend the day with! Despite the rainy day, we had a wonderful time. Delicious wine tasting and lunch at Casa Emma. Thank you again Simone for the wonderful experience! :)

Our trip with Marco was beyond what we expected from this private tour. He was knowledgeable, friendly and was a great guide, as we are first timers to Italy and unsure of the region we were visiting. The winery was great and loved visiting the other villages.

Simone was an excellent driver with great knowledge of the area. Our guide in Siena was very good as well, took us to a lot of hidden places in Siena. Lunch wine tasting was fantastic.

Our morning began with the prompt pick up of our driver Marco ( who’s English is very good)He told us about the beautiful areas we were driving through to Siena. Meeting our tour guide Claudia we walked and toured much of the city. The highlight was meeting her friend Emilio who allowed us to visit his studio as a master marble artist. The Palio race is just a few days ahead and the dirt track was laid. Claudia is so excited about the possibility of her Eagle neighborhood winning the race. It has been decades si c’è they have won. But each year gives a new opportunity. The winery tour was brief, which was okay with us as we have been on such tours before. The tasting and lunch were outstanding. Roxanne filled us with information about the five wines we enjoyed and the lunch prepare by her mama - delicious. Given the chance to ship bottles home was a plus and we will be eager to see them arrive. Our day was very good and we opted to ask Marco to skip the visit to Chianti. Our drive back to Florence was very picturesque.. it was a day filled with memories.

Our day in Tuscany was the highlight of our Florence trip. Cosomo was our driver and he was a pleasure to spend the day with. He drove us to Siena where we had a city tour with Vivianna. We were lucky enough to see the city set up for the Palio horse race which was two days away. The flags of the districts were on every corner and it added to the experience of learning what life inside Siena is like. Cosomo make reservations for us at Tenuta Casanova winery for a tour and lunch. The price is not included in the tour but I highly recommend including this in your day. The owner himself showed us around his winery and our wine tasting lunch was one of the best meals we’ve had in Italy. Last was an hour in San Gimignano, without a guide. I wished for more time here but we had a quick walk through and some amazing gelato at Gelateria Dondoli. I would love to go back and climb the towers one day. Overall a fantastic experience and I would highly recommend.