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Small Group Tuscany Day Trip From Florence with Chianti, Siena and San Gimignano

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If you want to enjoy the best of Tuscany’s culture, food and history without the hassle of trying to find your way around its beautiful but often confusing country roads, our Tuscany Day Trip From Florence with Chianti, Siena and San Gimignano is the perfect trip for you. All you have to do is indulge your senses with wine, food and medieval architecture that exists nowhere else in the world.
You'll start at
Caffè Lietta
Piazza della Libertà, 6/7/8 Rosso, 50129 Firenze FI, ItalyMeeting Time: 8:15 AM Departure time: 8:30 AM This tour meets in front of Cafè LIetta n.6/7/8 red, in Piazza della Libertà
See address & details
  • Pass by Piazza della Cisterna
    Pass by Torre Grossa (o Torre del palazzo del Podesta)
    Pass by Piazza del Campo
  • 1
    Duomo di Siena
    Stop: 60 minutes - Admission included
    Spared German bombing in World War 2, this time capsule of ancient, precarious-looking buildings is home to the Palio, one of the greatest and most dangerous horse races in the world. Your expert tour leader will immerse you in the unique history and culture of Siena as you explore its narrow streets before escorting you to the doors of the breathtaking Siena Cathedral.
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    Pass by Arno River
You'll end at
Piazza della Libertà
Piazza della Libertà, Firenze FI, ItalyPiazza della Libertà
See address & details
  • Travel in a comfortable, air-conditioned vehicle from Florence
  • A small-group tour makes for an intimate experience
  • Enjoy a traditional Tuscan lunch and wine pairings at a local vineyard
  • See Siena, the Chianti wine region, and San Gimignano all in one day
What to Expect
After meeting in the center of Florence, climb aboard your air-conditioned vehicle and make your way to the Tuscan countryside. On the way, pause at the Piazzale Michelangelo to take in views of Florence. Next, stop at the medieval town of Siena, a UNESCO World Heritage Site known for its beautifully preserved architecture. Learn about the Palio horse race that’s held here, and visit the opulently decorated Siena Cathedral. Continue on to the rolling hills of the Chianti wine region. Stop at a family-owned winery and farm for a tour of the vineyards and cellar, and then settle in for a freshly cooked Tuscan lunch with wine. Your final stop is the San Gimignano, a UNESCO-listed medieval town known for its soaring towers. Explore at your leisure before returning back to your vehicle for the ride back to Piazza della Repubblica in Florence, where the tour ends.
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Important Information
Departure Point
Caffè Lietta, Piazza della Libertà, 6/7/8 Rosso, 50129 Firenze FI, Italy
Departure Time
8:30 AM
Return Details
Piazza della Libertà, Firenze FI, Italy
  • Expert, English-speaking tour Leader throughout
  • Lunch and wine tasting in Chianti
  • Comfortable, air-conditioned transport
  • Professional driver (separate to Tour Leader)
  • Small groups of only 18 people or fewer
  • Entry/Admission - Duomo di Siena
  • Gratuities
  • Hotel Pick-Up/Drop-Off
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Additional Info
  • Confirmation will be received at time of booking
  • Please note that the cathedral of Siena is closed on Sundays during visiting time and subject to closure during special celebrations/festivities, including the Easter ceremonies. If this occurs during your visit, the alternative itinerary includes an explanation of the cathedral from the outside. The supplier is unable to provide refunds or discounts.
  • This tour includes a full lunch. If you have any dietary requirements please contact us before booking and we will do everything we can to accommodate you
  • Unfortunately there are no accommodations for guests with mobility impairments, wheelchairs or strollers on this tour.
  • The order of the sites visited may vary.
  • Tour is in English only
  • Please remember that the Cathedral is a holy place and attire must be appropriate for the visit. Both men and women are asked to wear clothing that covers at least the shoulders and knees. Walks cannot be held responsible for denied entry due to improper dress.
  • Not wheelchair accessible
  • Near public transportation
  • Infant seats available
  • Most travelers can participate
  • This tour/activity will have a maximum of 18 travelers
Cancellation Policy
For a full refund, cancel at least 24 hours in advance of the start date of the experience.
Traveller rating
  • 53
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Popular mentions
enjoyed a nice day visiting chianti, siena and san gimignano with a group of about 20. transportation from florence to tuscany was lovely and clean. guide (cannot recall his name -- lable? labo?) was well informed but also allowed down time on bus to enjoy the scenery. i
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Response from TakeWalksSF, Guest Relations Manager at Small Group Tuscany Day Trip From Florence with Chianti, Siena and San Gimignano
Responded 07 Nov 2019
Hello jonigit, Thank you for your review of our Tuscany Day Trip from Florence, we appreciate your feedback. I am so pleased to know that you enjoyed your day with us as we brought you through the beautiful countryside of Tuscany. It is certainly a stunning area to visit, and we are delighted that you chose us for the experience! We are great believers in improving wherever possible here at Walks, so we really do value all of your thoughts on your tour. Our understanding of the use of wine glasses is that it is preferable to change glasses between wines where possible, although that it is not always considered necessary - that is definitely something that we will be following up on with our partners in Tuscany. We hope to have you join us again soon, we would love to tour with you on your next visit! Warmest regards, The Walks Team
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Our tour guide was a very knowledgeable man (I’m sorry I can’t recall his name!) who shared lots of interesting tidbits on the history and culture of the Tuscany region. We started the tour with San Gimignano, had our lunch and wine tasting in the Chianti farmhouse, then
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Response from TakeWalksSF, Guest Relations Manager at Small Group Tuscany Day Trip From Florence with Chianti, Siena and San Gimignano
Responded 22 Oct 2019
Hi Kaylie_Tam, Thank you kindly for your thoughtful and insightful review of our Tuscany Day Trip From Florence, it is much appreciated! It is brilliant to hear that you found your tour and guide to be both informative and fascinating, as that is certainly what we would like all of our guests to experience with us. I understand, however, if there were certain aspects of the tour that you felt could be improved upon. It is always our aim to improve wherever possible, so we love to hear our guests' thoughts! You are absolutely correct, there can indeed be a lot of walking in our tours, and our Tuscany Day Trip is no exception! Due to restrictions on tour buses within the old town of Siena, we are limited to where we are able to park. As a responsible tour operator, we do our best to respect rules that are there to protect the integrity of sites that we visit, and we really appreciate our guests understanding about this. I can also certainly understand your desire to have stayed longer in Siena, as it is indeed a very picturesque example of an Italian medieval town. If we can tweak these two issues for guests' enjoyment in the future, we definitely will! As a wine enthusiast myself, I can completely empathize with your excitement to try a little of Tuscany's offerings. Up to 80% of the wine produced in the region is red wine, which may be why there was not quite as much variety as you were hoping for in your wine tasting session. I will pass along your feedback to the vineyard that we partner with, I am positive that they will use your considered feedback for the future too. We truly thank you for choosing Take Walks for your Tuscan introduction, and we hope that we have a second opportunity to impress you in the near future! Warmest regards, The Walks Team
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Our tour guide was Frederica, she was fantastic. She was very knowledgeable about the area and a very sweet lady. After reading other reviews of tours of 6 or 7 I realize we were not a small group, Our tour had 17 plus the guide and we were seated in a very large-capacity van.
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Response from TakeWalksSF, Guest Relations Manager at Small Group Tuscany Day Trip From Florence with Chianti, Siena and San Gimignano
Responded 01 Oct 2019
Hello 2houses, Thank you for your kind review of our guide Frederica, we are so glad to hear that you enjoyed her company so much. We sincerely regret, however, that you felt exhausted by the end of the day. We realise that it is a very long day and does include quite a bit of walking into and around Siena, and we are sorry if at any point this was not made clear enough for you. We aim to include very detailed descriptions of our tours, so that all guests can be fully informed about what is included in their tour prior to booking. Your feedback regarding this will absolutely be taken onboard so that we can improve upon this in the future! It is wonderful to hear that you loved Tuscany and the tour itself overall, and that you had a great time aside from the long walk. We would genuinely love to have you join us again in the future, if you are planning another excursion please do feel free to call us anytime. We love to help our clients with mobility issues find the perfect tour to match their needs and abilities! Warmest regards, The Walks Team
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We had a fabulous time on our Sienna, Chianti, San Gimignano tour. Our tour Guide, Daniella, was so fabulous. We had a small group of 6, which made the experience seem very private and personal. The driver, Francesco was also so wonderful, he took the time to learn about each
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Response from TakeWalksSF, Guest Relations Manager at Small Group Tuscany Day Trip From Florence with Chianti, Siena and San Gimignano
Responded 24 Sep 2019
Hello Travelforesta, It is wonderful to hear that you had such a fabulous time with our guide Daniella and our driver Francesco. Tuscany is a wonderful place to visit, but the guides and drivers really do make all the difference, which is why we are very proud to only work with the best! Thank you for choosing our company to tour with, and for your kind recommendation of our tour! Warmest regards, The Walks Team
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Comfortable bus and am informative tour guide. About 1.4 hours in San Gimignano (which is enough) and then a winery tour at Guardasteela; a gem of a boutique winery. We tasted 3 of their wines, plus a dessert wine - all paired with delicious foods, ample for lunch. We tasted a
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Response from TakeWalksSF, Guest Relations Manager at Small Group Tuscany Day Trip From Florence with Chianti, Siena and San Gimignano
Responded 22 Sep 2019
We're so glad that you enjoyed your Tuscany Day Trip with us! Thank you for taking the time to share your experience. We hope that the rest of your time in Italy was wonderful and look forward to the chance to tour with you again!
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About the operator
By: Walks
Best Cooking Class!
Loved having our cooking class with Lorenzo last month in Florence! Not only was the food delicious, but we had a
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Boca Raton, Florida
Perfect tour to see the sights.
We met up with our guide Roberto in the morning.(Im embarrased because im not 100% sure of his name, Please
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The highlight of Italy
Charles was a fountain of knowledge, so wise and captivating. He spoke on history, culture, art, engineering,
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Pasta and gelato making- 4 hours
One of our best experiences in Florence! We were met by Lorenzo , our chef, personally. Our class was in a
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Jennifer L
Great tour
I had never done a tour before. I prefer to explore on my own . I was so happy I decided to do this tour ! Angelo
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Craig W
Cosford, United Kingdom
Best of Florence Walking Tour with David & the Duomo - Excellent Experience
Our guide Angelo was incredible. His knowledge and understanding of the arts and the city was most excellent. Much
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Portland, Oregon
highly recommend this company
most of our tours throughout Italy were booked with them. they were very informative, super nice and definitely
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Singapore, Singapore
Informative and entertaining tour
The tour started on time despite the drizzle. Guide Angelo (in yellow raincoat) was knowledgeable and had a great
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Matt the guide was marvellous
Our guide Matt was so knowledgable, he answered every question put to him, his knowledge of florentine’s history
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Mayanne K.
Kuala Lumpur, Malaysia
Booked two trips with Walks & very happy
1) Walking Tour with Skip The Line Florence Duomo and Accademia: a good crash course on the city and its rich
Read more
Key Details
  • Duration: 10h
  • Mobile Ticket Accepted
  • Instant confirmation
  • Languages Offered: English
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