Private Tour of Siena, Pisa, and San Gimignano from Florence

Badge of ExcellenceFlorence, Italy

From $515.79

Price varies by group size

Select Date and Travelers

Free cancellation
Up to 24 hours in advance.
  • 9 hours (approx.)
  • Pickup offered
  • Mobile ticket
  • Offered in: English


Spend a day in Tuscany, visiting the cities of Siena, Pisa, and the medieval town of San Gimignano. With a private driver, benefit from a more flexible itinerary with plenty of free time. Enjoy a stroll through Siena’s history-rich Old Town, then admire views over the Tuscan countryside from San Gimignano. Finish with a visit to Pisa’s Piazza dei Miracoli, and snap a photo in front of the Leaning Tower of Pisa before your return to Florence. Lunch and entrance fees are at your own expense.
  • Private day trip to Siena, San Gimignano, and Pisa
  • Explore Siena’s historical center on your own
  • Learn about artists born in Siena such as Simone Martin
  • Admire the Collegiata of Santa Maria Assunta in San Gimignano
  • Stroll around the marble monuments of Piazza dei Miracoli in Pisa
  • Relax with a hotel pickup and drop-off service from Florence

What's Included

  • Hotel pickup and drop-off
  • Mercedes vehicle
  • Speaking driver
  • Free time in Pisa, Siena and San Gimignano
  • Bottled water
  • Wi-Fi
  • Lunch
  • Entrance fees (Cathedral of Siena is approx. 7 euros per person)
  • Local guides in Pisa, San Gimignano and Siena

Meeting And Pickup

Pickup points

Select a pickup point

Start time

08:30 AM

Pickup details

We also offer a pick up service to private homes and apartments

What To Expect

Leave your Florence hotel and travel out of the city toward Siena, your first stop of the day. Arrive in the Tuscan city for a self-guided walking tour around the UNESCO-listed historic city center.

The historical center is peppered with architectural delights, many of which abound at Piazza del Campo, the large square and heart of the city. Hear about Sienna’s connection to the artworld, too, as you learn about acclaimed Siena-born artists such as Simone Martini, Ambrogio Lorenzetti, and Duccio di Buoninsegna.

Then, leave Siena for the medieval hilltop town of San Gimignano with its famous 13 towers. Make the most of some free time to admire the fine architecture of the Collegiata of Santa Maria Assunta, then perhaps team views of the Tuscan countryside with a glass of the local Vernaccia wine (own expense).

Meet back with your driver, to travel to your last visit of the day, the city of Pisa. Stroll amid the white marble monuments of Piazza dei Miracoli, and pose for a photo in front of the iconic Leaning Tower of Pisa. Later, at a prearranged time, you’ll return to Florence, and end your day trip with a hotel drop-off.


1 hour Admission Ticket Free


2 hours Admission Ticket Free

Piazza del Campo

30 minutesAdmission Ticket Free

Torre del Mangia

15 minutesAdmission Ticket Free

Duomo di Siena

15 minutesAdmission Ticket Not Included

Chianti Road

30 minutesAdmission Ticket Free

San Gimignano

1 hour Admission Ticket Free

Piazza della Cisterna

15 minutesAdmission Ticket Free

Collegiata di Santa Maria Assunta - Duomo di San Gimignano

15 minutesAdmission Ticket Not Included


1 hour Admission Ticket Free

Leaning Tower of Pisa

15 minutesAdmission Ticket Not Included

Duomo di Pisa

15 minutesAdmission Ticket Free


1 hour Admission Ticket Free

Additional Info

  • Confirmation will be received at time of booking
  • Not wheelchair accessible
  • Stroller accessible
  • Near public transportation
  • Infants must sit on laps
  • Infant seats available
  • Not recommended for travelers with back problems
  • No heart problems or other serious medical conditions
  • Travelers should have a moderate physical fitness level
  • This is a private tour/activity. Only your group will participate

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.

Traveler Photos

See more

Traveler Tips

Nothing was to much trouble and extra visits to places of interest were included as well as lots of interesting information.


90 reviews
Total review count and overall rating based on Viator and Tripadvisor reviews
Reviews by Viator travelers.
Showing 1-10 of 90 reviews
Fab day
Rachel_E, Jun 2023
Sienna square amazing. San Gimignano lunch - fab. Wine tasting - v special winery. Lucca wall a treat to see. Driver very courteous and helpful. Worth recommending this trip.
3 In 1 Day
Christy_S, Jun 2023
This was a fantastic day and we would do it again, but be aware before booking that there is a lot of time on the road driving between the villages and the roads are quite curvy and bumpy.
Placido provided us with...
Anneclaire_E, Jun 2023
Placido provided us with a wonderful and memorable day. He picked us up from our accommodations on time after confirming our arrangements. Placido is an excellent driver and made navigating through challenging traffic seem effortless. He made sure we were able to see all our requested sights, and added some wonderful places along the way. We will definitely travel with Placido again in the future!
Brian_E, May 2023
Christian our tour operator was excellent. He guided us to an incredible winery for lunch and then off to a leather manufacturer. Overall the tour was 5 stars
Best Private Tour Experience of Tuscany
VinodKumar_M, Apr 2023
I am glad that I booked this private tour of Tuscany towns of Sienna, San Gimignano and Pissa with CiaoFlorence. It was one of the best tours we had so far on an international trip. Our experienced tour Guide Placido was an amazing guy. 30 minutes into tour and he knew exactly what our likes/dislikes are and took us to the best Wine tasting place in Chianti and other historical places within Tuscany. He was so accomodating to our requests to stop wherever we wanted to take pictures and videos. He was in no rush to complete the tour. He went above and beyond and took us to a place where we can see entire Florence City view during Sunset. So nice of him! I would highly recommend this tour and if possible, request for Placido as your tour Guide. I bet you won't regret. Ciao!
Great tour!
Angela_H, Mar 2023
Wonderful trip. Long but Placido (our driver) made it fun. San Gimignano is my new favorite place on earth.
A Beautiful Tuscan Day
Lynette_R, Mar 2023
We had the great pleasure of meeting Placido and spending the day with him in Pisa, San Gimingnano and Siena! He was incredibly welcoming, knowledgable and kind. We learned so much about Tuscany and the history of the area. All in all it was a fantastic day with lots of fun, laughter and absolutely stunning scenery.
Response from Host, Mar 2023
Dear Lynette, Thank you so much for leaving us a feedback! We are really happy to hear that you enjoyed your tour with us! We will forward your kind words to Placido, he will be very glad! Hope to see you again soon in Florence! Kindest regards, CiaoFlorence Staff
Unforgettable trip
Juan_M, Nov 2022
Excellent tour. Pretty much on your own, but tour operator provides city map and tips to follow along. Pretty comfortable ride and great views and tour guide Marco wad excellent!
Fun, personalized, and informative day trip
Theresa_N, Nov 2022
Our private tour guide, Christian, was wonderfully pleasant and informative. He managed our time well and was responsive to our preferences about details such as the number of wine tastings we wanted to experience. I would recommend the wine tasting at Fattoria Saint Appiano. In addition to the generous wine samples, the host served a lovely, multicourse meal. Our favorite tour visit was to San Gimignano. We enjoyed the medieval atmosphere.
Cristian is a 10/10
Nicole_E, Oct 2022
My husband and I booked a private tour of Pisa, Siena and San Gimignano and were lucky enough to have Cristian as our guide. This tour was definitely a highlight of our trip to Italy. We can’t say enough of our experience with Cristian. He was punctual, funny and very informative about each place visited. If you are looking for a once in a life time experience book with Cristian, you will not be disappointed!!!
JUDY_C, Sep 2022
Excellent tour guide with great knowledge of the cities as well as the surrounding areas and history of Italy.
Response from Host, Oct 2022
Dear Judy, Thank you for your positive review! We are glad to read that you enjoyed the guide as we take pride in the people we work with! We hope to see you again soon on one of our tours!
Great Trip!
Kelli_C, Sep 2022
This was a great trip! Our tour guide was amazing, the towns were beautiful, and the private van with AC made the trip very comfortable! I highly recommend!
Christian was the best tour guide!
Jennifer_K, Aug 2022
Our private tour with Christian was perfect! He gave us an educational background, managed our time extremely well and we felt like we also had a lot of autonomy to explore within the time of the tour.
Personalized tour
Rhea_D, Jul 2022
Our driver, Placido, was super accommodating. My teenagers were over the churches and museums. He completely tailored our day to what they wanted to do. We did Pisa in the morning and beach from there. He went out of his way to find places for us to hang out. An awesome day!
Definitely this was one our rememberable tours in Italy
Karim_A, Jul 2022
We had great time in Pisa, Tuscany and San Gimgnano we definitely Enjoyed every destination. We couldn’t do it all in one day without our private guide. Placido our guide is so familiar with the area, very friendly and made the trip a pleasant experience for us.
Amazing Day Tour of Tuscany
Deborah_H, Jul 2022
Christian was an amazing tour guide. We had an incredible day touring Pisa, San Gimignano and Sienna. We also had an amazing lunch at a beautiful Tuscan farmhouse and winery. Christian kept us entertained and informed about all the places we travelled to and through and made it really easy at each stop. The car is well air conditioned and very comfortable. We would highly recommend this tour and our guide.
Pleasant trip to Tuscany
Larry_K, Jul 2022
We modified the trip ( which was nice ) and left out Pisa, but added a small town in Tuscany called Greve. This was due to the heat, which is pretty hot right now. My son hadn’t been to Siena or San G. The Mercedes Benz was very nice but clearly the driver was a smoker, so there was a smell to the cabin. Our driver was knowledgeable about the areas we visited, but was more of a driver than a tour guide.
Excellent way to see the Tower of Pisa and learn more about Siena.
Matt_C, Jul 2022
Our guide, Osvaldo, was knowledgeable and entertaining. He had great recommendations for how long to spend at each stop and he was fun to be with.
Beautiful day
Einat_D, Jul 2022
The day was wonderful. We did not know that we should purchase tickets to climb Pisa ahead of time. When we got there, tickets were only available for after 1 PM and since this was the first city of the three that we visited, we were not able to climb pizza as we were there first thing in the morning and could not stay until noon. It would have been nice to know the order of the cities that we visit and to know to purchase tickets prior to the trip. The tour guides seem to not know this either so we were disappointed that we were unable to climb pizza. Otherwise the three cities were beautiful and the day was very memorable
Amazing day trip to Pisa, Siena and San Gimignano
Kathi_D, Jul 2022
Placido was our driver and he was phenomenal. He was the epitome of customer service. He was very knowledgable and made the trip enjoyable from the minute we got in the van. There were so many amazing things we experienced and I would do this trip again, but the highlight was the lunch at a winery that couldn't be beat. The winemaker treated us like family and took a personal interest in us. We tasted incredible wines with a very memorable lunch. I would recommend this tour to anyone coming to the Tuscany area. Ask for Placido--he is the best!
Tuscan Gems
Richard_V, Jul 2022
We had a fantastic time with Cristian. He was pleasant and knowledgeable, and made sure we were totally satisfied with our trip, even showing us attractions that added to our enjoyment. I would recommend Cristian as a Guide for anyone who wanted a to visit this area.
chris_m, Jun 2022
Our tour with Placido was a magical experience for our family of six. Communication regarding pick-up times was excellent & Placido was very flexible in making the day custom to our family. He was able to quickly plan & adjust schedules & arranged a wine tasting lunch that will be the highlight of our trip to Tuscany.
Christian was great!
Julie_B, Jun 2022
Our tour guide, Christian was fabulous! He was knowledgeable, interesting and friendly. He made our day very enjoyable. I will recommend my family and friends to use Christian when they travel to Florence!
Great experience
Natasa_T, Jun 2022
Placido was very informative and nice. He introduced some places that we didn't think to visit and without him, we’d miss them on our Tuscany tour. His English is perfect and we could clearly understand him during our whole day trip.
You can book a bus tour and get the same experience
Lilia_G, Jun 2022
The driver was nice, but for the tour all we got is a driver. For almost $900 we got a driver from point a to point b. The tour is misleading by showing the exclusion for tour guide, which I was prepared to pay separately but thought someone will be waiting for us to do the tours. Felt rushed to go thru towns to get to the set up lunch. Although drivers was nice to take us back to San Gimignano, where we spent another 30 min. Not enough to enjoy even on our own. If I wanted to rushed tour thru towns, I would have booked a bus tour not a private car. Felt very disappointed and missed opportunities to make it a great experience. If you get your booking, please make sure that what is excluded is actually set up to happen.
Wonderful experience!
Gary_S, Jun 2022
Christian was awesome, dropping us off right in the middle of each city and next to the main attractions to maximize time spent in these wonderful places. The Tuscany Lunch was fabulous and tasty and everything was right on time from departure to arrival. Private transport was the option for us. Thank you!!
Wonderful Private Tour!
diane, Apr 2022
Our tour operator, Placido, was wonderful! He made our family feel very welcome and comfortable on the tour and we enjoyed his stories as he pointed out spots along our route. We highly recommend Placido and this particular tour!
Fantastic full day experience!!
Lauren_L, Apr 2022
We had the most incredible tour with Placido! He was extremely friendly and knowledgeable. He arranged a wine tasting with lunch which was fantastic. We went from city to city, it was a well planned out tour. If you book this tour i highly recommend you ask for Placido!
Unforgettable day out in Tuscany
melanie_b, Apr 2022
We had a wonderful day. Our driver, Tiziano, was great - informative, friendly and an excellent driver. My husband has mobility issues so this was an excellent option for us. Tiziano was very good at knowing where to park close to the areas we wanted to see which maximised the time we had to explore. We would recommend this trip completely as you get a real feel for the beauty of Tuscany.
Trip to Tuscany
Monica_G, Mar 2022
The tour to Pisa, San Gimignano and Siena was absolutely amazing. Tíziano , our driver big kudos to him! He recommended this Ranch type restaurant/wine tasting that has wonderful food/appetizers for $35€ including the 9 types of wine tasting glasses. So much to see but timing was perfect we were able to see the most important monuments of each place. We ecommended this tour 100%. Thank you Tiziano you were amazing.

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Private Tour of Siena, Pisa, and San Gimignano from Florence


9 hours
Free Cancellation