Small-Group Tuscany Grand Tour: Siena, San Gimignano, Chianti and Pisa

Badge of ExcellenceFirenze, Italy

From $261.70

Select Date and Travelers

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


Explore the highlights of Tuscany with this full-day tour of Siena, San Gimignano, Chianti, and Pisa from Florence. Walk through medieval streets in Siena and San Gimignano. Have lunch and wine at a Chianti winery. See the town where Leonardo was born and admire the famous Leaning Tower of Pisa.
  • Full-day tour of Tuscany's highlights from Florence
  • Explore the medieval centers of Siena and San Gimignano
  • Enjoy lunch and a wine tasting in Chianti
  • See the world-famous Leaning Tower of Pisa

What's Included

  • Round-trip transportation by comfortable, air-conditioned minivan
  • Guided walking tour of Siena
  • Winery guided tour with wine tasting
  • Visit of medieval village of San Gimignano
  • Visit of Pisa with focus on "Piazza dei Miracoli"
  • English Speaking Guide
  • Lunch
  • Gratuities
  • Hotel pickup and drop-off

Meeting And Pickup

Meeting point

  • Florencetown
    Piazza Mentana, 3, 50123 Firenze FI, Italy

    Meet your tour guide at FLORENCETOWN BOOKING OFFICE, Piazza Mentana 2red FIRENZE (opposite the Arno River). Please be at the meeting point 15 minutes before the scheduled departure time.

Start time

08:00 AM

End point

This activity ends back at the meeting point.

What To Expect

Meet in central Florence and climb into an awaiting minivan to start your Tuscan tour. Enjoy the scenery en route to the first stop in Siena.

Take a guided walking tour through historic Siena to see the Piazza del Campo, where the city's Palio horse race occurs twice each summer. Learn about the 17 'contrade,' or districts, that compete in the Palio. Sample a local product before the end of the tour.

Continue to San Gimignano, a hilltop town famed for its many towers. Explore the Medieval center at your own pace, perhaps climbing up one of the towers for a better view of the countryside. Sample some gelato before departing.

Head for a winery located in the Chianti region. Soak in the atmosphere as you enjoy a typical Tuscan lunch and taste some of the winery's Chianti wines. Learn about how Chianti is made on a visit to their cellars.

Arrive in your final stop of the day, the city of Pisa, for a visit to the Piazza dei Miracoli where you can see the Leaning Tower of Pisa.

Your tour ends with drop-off at the original departure point.

Piazza del Campo

guided tour

2 hours Admission Ticket Included

Historic Centre of San Gimignano

free time to discover the amazing UNESCO Heritage Site

1 hour Admission Ticket Included

Additional Info

  • Confirmation will be received at time of booking
  • Not wheelchair accessible
  • Minimum drinking age is 18 years
  • Please advise any specific dietary requirements at time of booking
  • Near public transportation
  • Infant seats available
  • Most travelers can participate
  • This tour/activity will have a maximum of 8 travelers

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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47 reviews
Total review count and overall rating based on Viator and Tripadvisor reviews
Reviews by Viator travelers.
Showing 1-10 of 47 reviews
Brando our guide was...
Marni_G, Mar 2023
Brando our guide was fantastic! He shared so much history with us and was very personable anc knowledgeable. It was a lot to pack into one day, but worth it. We enjoyed each part of our tour and would like to spend more time in Tuscany on our next trip to Italy.
Excellent tour
Elias_K, Sep 2022
Guide was knowledgeable and friendly. Tour was plaisant and group people were nice. All stages were on time. Overall the tour was excellent.
Enjoy all of Italy
Arlene_D, Jul 2022
Our tour guide Rubina was wonderful. She had so much knowledge and gave us good tips on things to do. Was extremely pleasant to be with. Towns were great to see all the different ones.
MUST SEES IN TUSCANY, Be sure to ask for BRANDO as your driver/tour guide.
MATTHEW_B, Jun 2022
Our driver and guide BRANDO made this excursion particularly memorable. While driving from one historic and visually stunning site to the next, Brando charmed us, informed us and encouraged us to participate in the voyage. Oftentimes, strangers fall into silence as they travel between stops which results in a sleepy downtime from which you must rouse yourself at your next vista. However on our sojourn to Siena, Chianti Country and Pisa, Brando kept us engaged and entertained throughout our time and we all became a group of interactive, chatty and curious voyagers sharing photos and getting to know one another. The stops of this tour speak for themselves (they are 100% worth seeing) but you will be smart to book with FLORENCETOWN TOURS and be sure to ask for BRANDO as your guide!
Small-Group Tuscany Grand Tour: Siena, San Gimignano, Chianti and Pisa
Daniel_M, Nov 2021
Once again, we were lucky enough to visit during the slow season so we essentially had a private tour. Brando did an amazing job of juggling presenting the information with giving us space to enjoy an intimate tour. Would highly recommend!!
Great experience!
Gary_R, Sep 2021
Fantastic day! My mom and I had such a memorable experience. Brando was a phenomenal guide. Personable and informative, we learned so much about the Tuscan region. Highly recommend this company and their tour options! We loved the itinerary and felt like we saw all the main highlights. We also felt very safe with the precautions taken during the ongoing health crisis.
Beautiful trip into Tuscany
rtmarino129, Sep 2019
The tour guide was wonderful. She took us to Siena where we received a short tour of the town, the on to San Gimignano, the winery for a delicious lunch and on to Pisa. It was a long day but well worth it.
Lucca was our guide on this...
Susan S, Jun 2018
Lucca was our guide on this wonderful tour. He was so knowledgeable about the entire region and was full of fun and energy. We started in Siena and we were met by a separate expert tour guide for the city. My husband and I had visited Siena before but this time we really learned a lot and appreciated it much more. In San Gimignano we had an hour of free time to stroll through the city and sight see, shop or sit at an outdoor cafe. Unfortunately for us, when we arrived in Pisa the sky opened up and it was raining so hard no one wanted to get out of the van! I decided that I wanted to see the leaning tower enough to get drenched and so jumped out and snapped a few pictures and ran back! Everyone loved the pictures so we all went back - even though it was raining. Then it was on to Lucca where we stopped for a treat at a local cafe. All in all, it was a very nice day and we truly enjoyed it! The best part was just driving through Tuscany and looking out at the beautiful hills and fields. What a wonderful way to see the countryside!
Except that it was a bit squuezy in...
Jaclyn C, Jan 2018
Except that it was a bit squuezy in the 9-pax vehicle, everything was great. Very relaxing and the guide was very patient, attentive, and enthusiastic in his work. Keep up the good work Ricardo!
Our tour leader was great! San...
Vicki_T, Sep 2017
Our tour leader was great! San Gimignano was great and I really enjoyed the time we spent in this village. However on this tour I would suggest less time be spent in Pisa and Luca.
Excellent tour, Highly recommended...
Gorina G, Sep 2017
Excellent tour, Highly recommended. Very nice and informative guide.
We absolutely loved this tour. 4...
Brian C, May 2017
We absolutely loved this tour. 4 towns and a winery tour seems like a lot to do in one day, but the tour was so well organized that we were truly able to enjoy all these areas without feeling rushed. Our guide Chris was excellent - I can't recommend him highly enough. Wonderful!!
I was kind of skeptical in joining...
Urbano_B, Dec 2016
I was kind of skeptical in joining such a tour that would visit so many places in one day, as I usually prefer rather relaxed and slow-paced experiences. Well, thank god I joined it! Discovering the whole Tuscany would probably take you a lifetime, but I was staying in Florence only 3 days and this tour turned out to be the best opportunity to really have a sense of true Tuscany. From the most renowned and magnificent places, such as Siena and Pisa, to enchanting San Gimignano and charming Lucca, not to mention the wonderful winery we visited, you really can breathe the authentic Tuscan essence, feeling immersed in it for a full day. The transfers from one place to the other vary in length but I felt them as part of the adventure: the landscapes you drive through with the minivan are gorgeous! Vineyards, olive groves, gentle hills... well, in a word, Tuscany! And, by the way, even though at the end of the long day you might feel tired, it still felt like a relaxed journey. I think this is all due to the very small group and the professionality and passion of our guide. The wonderful memories - and hundreds of pictures! - from this tour will be the best souvenir we'll bring back home from this Italy vacation. Thank you!
Wow! Never seen so many beautiful...
Urbano_B, Nov 2016
Wow! Never seen so many beautiful places in one day before! Our group was only 8 persons so it felt almost like a private tour, and this does make the difference in a full day trip like this. All the locations are well worth a visit like this. Wonderful Siena, quaint San Gimignano and Pisa with its leaning tower are classic destinations in Tuscany, cannot miss them, and that's because they really can fill your eyes with beauty. But I had never heard about Lucca, before reading about it on a great Tuscany guidebook, and trust me, you'll be surprised by its history and charm, plus the fact that it's definitely less touristy. Add to this a wonderful ancient winery in a medieval villa and castle, with a nice lunch and great Chianti wines - that can inspire a little nap during the following transfer to Pisa - and a fun and knowledgeable guide like Cristian, and you've got the perfect Tuscan day!
Fantastic tour, seen lots of...
Urbano_B, Nov 2016
Fantastic tour, seen lots of incredible things in Tuscany and great guide! It's a full day tour, about 12 hours, so quite long, but definitely worth it if you are not spending many days in Florence and Tuscany and want to discover the most of it in the shortest time. I've seen other similar tours around but with much bigger groups, and didn't want to end up in a 60-seat coach following a flag: this is the only small group tour of this kind I've found we were 8 people on our tour!. More expensive, but a totally different feeling: at the end of the day you feel you've found new friends among the other passengers, and especially talking about our great guide Cristian. Siena is magic and our local guide there, Benedicta, was knowledgeable and extremely passionate about her town. The free time in the little jewel hamlet, San Gimignano, was much appreciated as this is a very small medieval village and you can stroll around by yourself at your own pace. The Chianti winery you visit is immersed in the vineyard hills of the wine region, with a medieval tower you can sometimes climb gorgeous views from up there, an authentic ancient cellar still used nowadays and good quality wines you get to taste some of them. You also have lunch here, with delicious Tuscan cold cuts and pastas. The leaning tower in Pisa is... well, the leaning tower, as you've seen it in thousands of selfies, but much more impressive pictures don't do justice to its dramatic leaning and with a gorgeous square, cathedral and baptistery around. I had read another review about Vinci being a pointless stop... well, I cannot say anything about Vinci as right before leaving with the tour the local company that runs it informed us that the Vinci stop would be replaced by a visit to Lucca... and Lucca proved to be an unknown to me magic treat! What a lovely quaint medieval town! We even had an aperitivo in its unique amphitheatre square! Not to be missed! So, all in all, it's not been the most economic thing I've done in Italy, but it's the first one i would do again!
Was really disappointed with this...
Patricia C, Sep 2016
Was really disappointed with this tour: Siena - This was brilliant, the tour guide was from the area and had brilliant local knowledge San Gimignano - This is self-guided. You get a little information driving to this location, but are on your own when you arrive approx 1 hour. Beautiful place, although it was very busy. Chianti Winery tour / lunch - Disaster!! I actually found this part embarrassing! The lady from the winery clearly doesn't do tours - very little information, and at one point we were shown upstairs to a virtually empty room with some old machines that had nothing to do with the tour. It was cringe-worthy. The lunch was fine with tasting of 4 wines. Vinci - Pointless stop. We went to both museums, one of which is currently under construction. Unless you have an interest in engineering, there is nothing at this stop for you approx 1hr This was also self guided. Pisa - Leaning Tower 1hour. This was fine - time for a walk around the square or trip up the tower. This was also self guided. I would not recommend this tour - there are so many other trips out there with good reviews. Really regret taking this one. PS - The tour guides were lovely, the tour itself, and the information provided did not live up to expectations!
Muito bem organizada.
sfasouza, Sep 2019
Gostei muito. Minha unica sugestao seria diminuir o tempo em Pisa e aumentar o tempo em Siena. Empresa confiavel, recomendo!