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Private Tuscany Tour: Siena, Pisa and San Gimignano from Florence

Badge of ExcellenceFlorence, Italy
Private Tour of Siena Pisa and San Gimignano from Florence
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From $634.52

Price varies by group size

Select Date and Travelers

up to 24 hours before the experience starts (local time)

  • 10 hours
  • Pickup offered
  • Mobile ticket
  • Offered in: English

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Overview

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

  • Door to door Hotel pickup and drop-off
  • Fully-fitted Mercedes vehicle with Free Wifi on board
  • Expert Professional Driver at your full disposal
  • Free time in Pisa, Siena and San Gimignano
  • Bottled water
  • Air conditioning and USB charger on board
  • Direct access to the historic centre of UNESCO Listed Art Cities
  • Flexible itinerary
  • Lunch
  • Siena Cathedral ticket is €10 approx.
  • San Gimignano Pass €13 : includes entry to the Civic Museums and Collegiate Complex
  • Leaning Tower of Pisa ticket is €20 approx.

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.

Florence

1 hour • Admission Ticket Free

Siena

2 hours • Admission Ticket Free

Piazza del Campo

1 hour • Admission Ticket Free

Torre del Mangia

30 minutes • Admission Ticket Free

Duomo di Siena

30 minutes • Admission Ticket Not Included

Chianti Road

30 minutes • Admission Ticket Free

San Gimignano

1 hour • Admission Ticket Free

Piazza della Cisterna

15 minutes • Admission Ticket Free

Collegiata di Santa Maria Assunta - Duomo di San Gimignano

15 minutes • Admission Ticket Not Included

Pisa

1 hour • Admission Ticket Free

Leaning Tower of Pisa

30 minutes • Admission Ticket Not Included

Duomo di Pisa

30 minutes • Admission Ticket Free

Florence

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

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Reviews

5.0
115 reviews
Total review count and overall rating based on Viator and Tripadvisor reviews
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Reviews by Viator travelers.
Showing 1-10 of 115 reviews
Wonderful and accommodating driver.
Cindy_B, Apr 2024
Beautiful scenery. Guide was very knowledgeable and personable. Lunch was arranged at a private winery. We left our umbrellas in our apartment and our driver kindly provided them when it rained unexpectedly. We would highly recommend Christian our driver for the day.
Memorable Tuscany tour
Stacey_B, Mar 2024
Cristian was our driver guide for our day in Tuscany. It was a lovely day and we were able to see Pisa, San Gimignano and Siena. Additionally, Cristian arranged for us to have a lunch with wine pairings at a vineyard. This was a last minute add on that my husband and I greatly enjoyed, and even our children, who are too young to drink, enjoyed! Then, at the end of the day, he took us to Piazza Michelangelo for incredible evening views of Florence. I would highly recommend this tour - it was a long and full day that was truly memorable!
Great tour, wonderful driver!
BEATRIZ_J, Jan 2024
My family and I had a wonderful time with this tour. I read the description, inclusion and exclusion so I asked CIAO FLORENCE to help me book all the tour tickets and lunch (at this wonderful winery with wine pairings) that we wanted to do for additional costs. It’s all worth it. Our driver VALENTINO was the best!. He was on time and always communicating on where and when we would meet for every stops. He was very informative on historical sites and great insights on them. He pointed to us what we must see on our stops. We also had random conversations that made our commute fun! I totally would recommend this tour. WE like paying for comfort and if you have a kid / kids, I highly recommend this tour. I highly recommend Valentino as the driver as well. To make this successful, you have to communicate your needs ahead of time and CIAO FLORENCE made it easy, they started a WhatApp channel right away after booking.
Perfection
jay_h, Dec 2023
Valentin was very professional. Everything was perfect Informative and on time Will do it again Great for families
Perfect Day!
Cheryl_N, Nov 2023
Probably my favorite tour of the entire trip. Our tour guide customized the tour for a perfect trip for the three of us. I would take this tour again and recommend it for anyone visiting the Tuscany region.
Cristian the consummate Florentine
Amy_R, Oct 2023
Cristian is the most passionate and knowledgeable tour guide in Tuscany. We had a memorable private tour of Pisa, San Gimignano, and Siena. Highly recommended.
Well worth the day
Tina_T, Oct 2023
This tour was fantastic and made even better than we could have imagined due to our excellent driver PLACIDO. There is only one Placido! He gave us so much background and history of the entire Florence/Tuscany area and tailored our trip to what we most wanted to do. We spent just enough time in Siena and Pisa to see the sights and experience the difference from the city and then he took us to the most spectacular area of San Gimignano to a wine luncheon at Corbucci winery. Everything was top notch and I would recommend this trip and especially request PLACIDO to anyone who goes.
Not what we were expecting from reading the tour info and reviews!
JanM_B, Sep 2023
Let me start off by saying we do not blame the driver at all for this experience. It's totally on the tour operators. I felt bad for the driver that he was dropped into this English speaking experience he did not seem at all familiar with. This was supposed to be an English language tour, but the driver spoke almost no English and didn't seem familiar with the tour. We gave up after asking a few simple questions about our surroundings or things we saw on the drive that he didn't comprehend. We are giving this two stars because we did see most of what we wanted by fumbling around on our own with Google Maps after being dumped off with no suggestions, recommendations or guidance. Unlike some others, we were aware that there would be no tour guide, but the reviews are filled with glowing accounts of great drivers who spoke English, imparted knowledge, and even assisted in getting them a lovely lunch and wine tasting at a winery. There was none of that in this tour for us. We asked about the possible winery lunch, and he was clueless and didn't understand what we were asking. We finally grabbed a bad pizza on our own in Siena because we had no clue where to eat. We'd never been to any of these places before. I don't think the driver was very familiar either since he came in for this tour from Rome. Obviously, the value in this tour is all about the driver's knowledge of previous tours and the ability to communicate well in English. It sounds like he got zero information on the basic tour before he was tossed in to drive it. Unfortunately, we didn't get a driver who could answer any questions. This also wasn't a door to door pickup and dropoff. We were dumped before Piazza Della Signora and had to walk back to Piazza Del Pesce at the end of the tour. I do not think we got what we paid for with this tour. It was specified as an English language tour. Unforunately, I'm now terrified about the other private driver tours we booked on Viator in the next few weeks. I'm really hoping they are better for the money we paid. At the very least, I'm hoping the drivers speak enough English to answer basic questions. Tour operators...please do better. Your customers deserve the tour they were promised in the description. Please stop using drivers who don't speak English for a tour that was specifically billed as an English tour. It's very uncomfortable to spend 8 hours with someone who can't answer simple questions. Kudos to the driver for trying, but it wasn't fair to him, either.
Tuscany Dream Day
Christine_S, Sep 2023
Placido was a fabulous guide! Curated a perfect day to check all our boxes and then some. 100% recommend!
What an incredible experience!
Melissa_T, Aug 2023
My husband and I had a private tour of 3 fabulous villages/cities in the Tuscany region today. What a great day for driving through the vineyards. Our driver, Placido, was fantastic. We couldn't have asked for a better or even a nicer driver than who we had today. He was engaging with us and he made great suggestions of things to see in each of the stops. I liked that we were able to customize our stops. Such as, staying longer or shorter in each of the villages. He even suggested a lunch option for us at a private winery in the Tuscany vineyards. We had such a great day and we just wanted to say "thank you so much, Placido". You are the best!
Excellent tour
Krishna_S, Jun 2023
We had a great experience with Ciao Florence, and Cristian our guide. We were able to see beautiful parts of Tuscany and learn about the history behind them. Cristian was very friendly, and made the whole experience fun and enjoyable! The lunch in the vineyard was as nice but winery folks were doing too much of pitching of their wine to buy, which was bit awkward.
Should be titled: Private driver to Siena, Pisa, and San Gimignano from Florence
Michelle_K, Jun 2023
Great driver but I wish I read the description carefully. This is ONLY A DRIVER. Tours must be booked separately (more $$). The title is misleading. We had a very expensive drive (driver was amazing), but was not happy when no tours or tickets could be purchased at the last minute. Book this if you want to go on a car ride.
Unexpected Surprise Winery Lunch Blew Us Away!
Andrew_K, Jun 2023
We (family of 5; 15, 14, 7 yr olds) had a great time! It was 97 degrees, and only our second day of a 9 hour time difference jet-lag, so I was worried going into it. Out driver/guide was awesome! So sorry I missed your name! So friendly, gave the right amount of info, and instantly felt like a friend. The Mercedes van had A/C and I sat in the way back with no problem at 6’2” (so my daughter could sit in middle as she has a tendency to get car sick). No one did get car sick at all. We started in Pisa and 20 min was perfect to hop out and get our shots in the heat. The drop off/pickup point is right on top of the area. No extra walking at all. So convenient! We ade a stop for bathrooms and drinks at a gas station and on to San Gimignano. Again, drop off right at the entrance. No extra walking at all! They are hyped for “World Famous/Winning” gelato. It was indeed the best we have ever had…and our kids are critical. 1 hour was a perfect amount of time to walk up the street, get gelato, and walk back down stopping in the shops. The main drag is lined with tall building which provide shade, so the hill isn’t that bad, even in the heat. Next, was the highlight of our entire Italy trip so far (writing this while still on the trip). We had an unexpected stop for a lunch/wine pairing at Fattoria Sant’Appiano. Wow! This is what we think of when we think of Tuscany! Amazing food and wine pairing on a hill top. We can’t say enough of this place. We didn’t think we would get this Tuscany experience bringing the kids on the trip, but this will be a highlight of our lives. The food here was the best we had in Florence and the owning family is beyond kind and welcoming. If we make it back to Tuscany, we will look to even stay here. The lunch was a multi course meal with the absolute best Ragu we had as a dish, and another dish with some sliced pork with a Chianti reduction that blew my mind. It looked so simple, yet tasked like an explosion of Thanksgiving flavors. We would go out of our way next time to come back here. Our kids had enough of the heat at that point, so we skipped Siena. We knew this was likely due to the jet lag from Los Angeles and a big reason why we booked a private tour…for the flexibility. We were able to head back to Florence after lunch. It was definite worth booking. We could have booked the train/bus to Pisa, not getting to experience San Gimignano and especially Fattoria Sant’Appiano made it absolutely worth it. I am not exaggerating when I say Fattoria Sant’Appiano is a lifetime memory. Priceless!
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!
Excellent
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
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