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

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

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2 adults
Free Cancellation up to 24 hours in advance
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Exploring the Tuscan countryside is a must when you visit Florence, but arranging your own transportation can be tricky. This tour makes it simple to see the area’s highlights in a single day. Visit Siena and its famous cathedral, do some wine tasting in Chianti, and see San Gimignano. Lunch is included, meaning you can pack light, and a small group size means plenty of time to ask questions.
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
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  • Pass by Florence
    Pass by Tuscany
    Pass by Siena
    Pass by Duomo di Siena
    Pass by San Gimignano
    Pass by Torre Grossa (o Torre del palazzo del Podesta)
    Pass by Piazza della Cisterna
You'll end at
Piazza della Libertà
Piazza della Libertà, Firenze FI, ItalyPiazza della Libertà
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  • 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
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
  • Pasta-making demonstration
  • Lunch & wine tasting in Chianti
  • Gratuities
  • Hotel Pick-Up/Drop-Off
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Additional Info
  • Confirmation will be received at time of booking
  • 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
  • Not wheelchair accessible
  • Near public transportation
  • Infant seats available
  • Most travellers can participate
  • This tour/activity will have a maximum of 18 travellers
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
jonigit wrote a review Nov 2019
10 contributions
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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Date of experience: October 2019
Response from TakeWalksSF, Guest Relations Manager at Small Group Tuscany Day Trip From Florence with Chianti, Siena and San Gimignano
Responded 7 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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Kaylie wrote a review Oct 2019
Singapore, Singapore35 contributions6 helpful votes
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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Date of experience: October 2019
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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3dogs wrote a review Sep 2019
San Diego, California3 contributions
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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Date of experience: September 2019
Response from TakeWalksSF, Guest Relations Manager at Small Group Tuscany Day Trip From Florence with Chianti, Siena and San Gimignano
Responded 1 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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Travelforesta wrote a review Sep 2019
2 contributions1 helpful vote
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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Date of experience: September 2019
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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David O wrote a review Sep 2019
Delray Beach, Florida79 contributions24 helpful votes
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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Date of experience: September 2019
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

Don’t take it from us – here’s what people have to say about this operator.

By: Walks
Skipped the line
What a great Idea I am so glad we got these tickets because we would of waited for hours otherwise. Certainly wort
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Insightful tour of Florence!
When we first planned our trip to Florence, we were not planning to do a tour that included the Accademia (we were
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Best Cooking Class!
Loved having our cooking class with Lorenzo last month in Florence! Not only was the food delicious, but we had a b
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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 correct
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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, polit
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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 wonderfu
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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 w
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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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highly recommend this company
most of our tours throughout Italy were booked with them. they were very informative, super nice and definitely wor
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Informative and entertaining tour
The tour started on time despite the drizzle. Guide Angelo (in yellow raincoat) was knowledgeable and had a great s
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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 w
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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 histo
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Melissa K
A wonderful day!
This was our first full day in Florence and Matt was a superb guide! His passion for his city and the wondrous art
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Absolutely loved this.
Four of us took this cooking class with Raffaella. We all loved it. She was friendly, a great instructor and really
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Good tour with history of Florence and the different sites
We were able to see a lot of the different areas and art in Florence. The guide was very knowledgeable and was very
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Key Details
  • Duration: 10h
  • Mobile Ticket Accepted
  • Free Cancellation up to 24 hours in advance
  • Instant Confirmation
  • Languages Offered: English
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