Walks of Italy

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Tuscany from Florence

Key Details

  • City: Florence
  • Duration: Approx. 10 hrs
  • Start Time: 8.30 AM

Tour Highlights

  • World-famous for its hill towns, scenery, cuisine and wine; there are a lot of reasons to visit Tuscany. Experience ALL of these in the most authentic, relaxed way possible on our Tuscany tours from Florence. Taking the hassle out of your visit so you can sit back, relax and enjoy a glass of wine (or two).

  • You’ll visit the beautiful medieval town of Siena, see its cathedral and wander its atmospheric streets; enjoy lunch and wine-tasting at an authentic Chianti farmhouse and vineyard; and explore pretty little San Gimignano.

  • Throughout your day trip from Florence, you’ll be accompanied by a friendly, English-speaking Tour Leader. They’ll teach you about the sites you pass, the towns you visit and the food and wine you consume. Meanwhile, small groups of 14 or fewer & luxury air-con transport make for a more relaxed experience.
Inside Siena Cathedral, Tuscany Inside Siena Cathedral, Tuscany Inside Siena Cathedral, Tuscany Inside Siena Cathedral, Tuscany Inside Siena Cathedral, Tuscany Siena Cathedral from outside Siena Cathedral from outside Piazza del Campo, Siena Wandering the streets of Siena on our Tuscany day trip Wandering the streets of Siena on our Tuscany day trip Siena town Siena town Explore the vineyards of Tuscany Learn how balsamic vinegar is made Explore a local vineyard with your host Explore a local vineyard with your host Explore a local vineyard with your host Sample famous Chianti wine Sample famous Chianti wine Lunch on the terrace at a Tuscan vineyard Sample local delicacies, always seasonal Sample local delicacies, always seasonal Sample local delicacies, always seasonal Sample local delicacies, always seasonal Sample local delicacies, always seasonal A day to remember in Tuscany A day to remember in Tuscany Lunch is at a working farm Balsamic vinegar, made at the farm Our lovely hosts Tuscany food, fresh from the source Chianti vineyard Climb the tower at San Gimignano



Our day starts in central Florence, where you’ll meet your tour leader and private driver for the day – or maybe two drivers. We never use vehicles larger than 8-person capacity on this tour, as minibuses and cars allow us to drive you right up to the main square in Siena. If your group is split, your tour leader will take it in turns to ride in each vehicle, ensuring you all get the background you need to really enjoy your day.

Before we head for the hills we have a special surprise for you. We’ll take a short spin up to Piazzale Michelangelo, on the other side of the Arno, for the best view in all of Florence. Then we’re on the road and off to Tuscany.

The first stop on our Tuscany tour from Florence is beautiful Siena. Miraculously spared the bombing of WWII, Siena is an incredible example of medieval town planning and architecture. Your tour leader will introduce you to the city on a short, guided walk and give you a bit of background; including Piazza del Campo, the town square where Siena’s historic Palio horse racing contest still takes place every year.

How you spend your time now is up to you! Your tour leader will give you some tips and will also hand you tickets to visit the Cathedral on your own. We really recommend you go inside – as beautiful as it is from outside, the Cathedral is even more astounding inside.

N.B.: The Siena Cathedral is closed to tourists on Sundays. If you visit on a Sunday we regret to inform you that this option is not open to you.


Of course no Tuscany tour would be complete without a visit to the wine region! Famous for its wine of the same name, Chianti is a beautiful area full of rolling hills and picture-perfect farmhouses. It’s at one of these postcard spots we stop next! You will enjoy a tour of the farm, vineyards and wine cellars, before settling in for lunch and a guided wine tasting, included in the price of the tour.

What you eat will depend on the season. Tuscan cuisine is famously linked to its produce, using the best and freshest ingredients for the most hearty, delicious dishes. This is Italian food at its finest.


Then it’s on to the little town of San Gimignano, so pretty and architecturally significant it’s a UNESCO World Heritage Site. As you walk its streets in search of Tuscan delicacies to bring home, take the time to soak in the atmosphere and keep an eye out for the famous tower houses; a beautiful legacy of medieval planning. Those inclined should climb the city’s campanile for the other best view in Tuscany.

From start to finish the emphasis of our day trip from Florence is on indulgence: Indulge in stunning scenery, delicious wines and lazy strolls on our all-inclusive Tuscan adventure. We’ve taken care of all the details so all you have to worry about is how much Chianti wine you can fit in your suitcase.

Sites visited

  • Piazzale Michelangelo, for views over Florence
  • Siena
  • Chianti farmhouse & vineyard
  • San Gimignano


  • Expert, English-speaking Tour Leader throughout (may be split between 2 vehicles for journeys)
  • Visit to Siena Cathedral (except Sundays)
  • Lunch & wine tasting in Chianti
  • Comfortable, air-conditioned transport no larger than 8-person
  • Professional driver (separate to Tour Leader)
  • Small groups of only 14 people or fewer


5-stars from over 565 Customer Reviews

Loved the tour. Well thought out. Nice van and driver. Elinor was our guide and she was excellent. Even recommended the best gelato in the world (and it was!) I would definitely recommend it to see some of the Tuscan countryside.
This tour was terrific and Eriza was absolutely top notch!
This tour was terrific and Eriza was absolutely top notch!

Important information

Before you travel, please read our important notes about possible disruptions & site entrance requirements

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.

If you are traveling with a small child and stroller, please let us know before booking as we will need to reserve space on the bus for both.

The Siena Cathedral is closed on Sundays and Festivities.

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Offer only valid on listed tours purchased at the same time. Non-transferable.
Florence Food Tour
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Uffizi Tour & Tickets
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Florence Duomo & Accademia
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This was the BEST tour we had during our 15-day trip to Italy. It was the biggest investment, but it's true - you get what you pay for! I would highly, highly recommend this tour. The guide was fun, friendly and informative. The lunch and endless wine was such a treat. And we really enjoyed both Siena and San Gimignano. Book this tour, you won't regret it!
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Loved the tour. Well thought out. Nice van and driver. Elinor was our guide and she was excellent. Even recommended the best gelato in the world (and it was!) I would definitely recommend it to see some of the Tuscan countryside.
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The trip was one of the best we've had! Chill and friendly guide, comfortable coach, professional driver. What's more important is the content of the trip: Siena, San Gimignano, and the Chianti countryside is simply enchanting, and the lunch and wine tasting gave a new appreciation for good food and wine. Simply the best! (My only suggestion would be to give us 10 more mins at the Siena Duomo. We only stopped for around 15 mins and it was too fast to take in the architectural wonder!)
This tour was terrific and Eriza was absolutely top notch!
This tour was terrific and Eriza was absolutely top notch!
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Really enjoyed the tour
Eriza was gracious, kind, and fun. Drivers were excellent. By the end of the day it was like our group had been on outting with old friends.
Eleonora was a little fireball!!! She was enthusiastic, fun and informative. Although it was a long day, it passed too quickly! I would have loved a bit more time in Sienna. It was either see the Cathedral or shop, not time for both. The lunch and wine tasting was a highlight! Can't wait for our wines to arrive here at home!! Fabulous day!!!
One of the best tours I took in Italy
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Nebojsa was the Best Tour Guide Ever!!! He was very informative and knowledgeable . He was interactive and we all felt very involved while having fun. You can tell he was very passionate of his dedication and he wanted us to have a great time . Nebojsa was Awesome ! Our driver Simone was great too! He drive safely . Walks of Italy is the Best! Can’t wait to take Walks tour in Rome .
We thought this tour was excellent. Eriza was very knowledgeable, helpful and personable. Since she grew up in Siena she knew it well and provided commentary throughout the entire time in Siena. My daughter took the same tour on May 31 after we raved about it but her guide provided little info on Siena (just kind of left them to explore on their own) which was disappointing to hear. We were fortunate to get Eriza. We had an outstanding visit to Siena. The winery visit was excellent. Lorenzo at Poggio Amorelli did an excellent job.
Really enjoyed the day. Eleonore was delightful and very knowledgeable. The highlight for me was our lunch and wine tasting in San Gimignano. Our lunch in a barrel room was excellent, the wines selected by Tenuta Torciana were wonderful. So thanks to the winery. I also want to thank Eleonore for taking time with me after the tour to go through the ATM process. This was actually our third tour. We did Pompeii and the Vatican while in Rome all with Walks in Italy. Would highly recommend your group to my friends. Thanks. Sam Wilson Tucson, Arizona
Our Tuscany Day Trip was excellent... Valentina made it so interesting with her knowledge and her understanding of the Italian culture.. she answered all our questions and was very considerate to all in her group.. Our group was small which made it so delightful and memorable!
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Well organised n well taken care.thanks.will surely recommend ur company to others.
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The only negative point of the day was the lunch and wine at the winery we stopped at. The wines were honestly the only bad wines I had during my entire visit to Italy (and we drank a lot!). The food was just ok, not up to what I came to expect for Italian food.
Our guide was absolutely wonderful! She was informative, passionate about the area and super friendly. Everything about the trip was amazing but she really made it extra special. Our driver was great too!
This was a lovely tour, and we enjoyed the day. Both of us wished that there had been more time to explore the 2 towns, as that aspect felt quite rushed, actually. The lunch was good and the wine delicious. Honestly, we could have skipped the first portion - the view over Florence - as we would have been happy to walk up the hill on our own time (not on the tour). This stop took up half an hour that could have been spent in the other towns. Also, we got back to Florence half an hour earlier than advertised, so again, another half hour that could have been spent in the towns. Overall, this was a great day - but it would be great to have a bit more time to wander through the beautiful towns. Thanks again! :)
Excellent and well worth the time for this tour. Guide was magnificent.
We were delighted to end up in Nebo's group for the second day in a row. He is very knowledgeable and friendly. Though I'm sure he does many of these tours at this time of year, he did recognize us from the day before. All of the stops on this tour were well chosen. We very much enjoyed the entire experience. Even our driver offered information about sights along our way. Thank you!
This was a very good tour and it met our expectations. Our guide did a good job balancing the amount of time in Siena, San Gimignano and at the vineyard/lunch (including appropriate free time vs. structured time), which is a difficult task. She offered good information in both towns and was very personable. The wine tasting and lunch was nice too. I have a few recommendations to make the tour even better in the future: 1) It would be helpful to have earphones on this tour like most of the other Walks of Italy tours. This would allow us to hear from the guide while walking instead of only while huddled up. It might allow us to take a less-rushed walking pace. The walking pace was difficult for my 70 year old parents -especially on the hills. 2) It would be nice to have the guide go inside of the Siena cathedral with us to tell us about the amazing interior. Although our guide gave us a preview before going into the church, it was less impactful than if we were learning about each thing while looking at it. I was a bit jealous of the other other tour groups who had their guides with them inside of the church and I eavesdropped to learn a lot more than I did from our guide's preview. 3) When possible it would be helpful to huddle the group in the shade rather than in the hot sunshine, especially when shade is nearby. Having ear pieces could also allow people to listen from the shade. 4) It would be helpful for tours involving transport to recommend to guides and drivers that they wear less perfume than normal. Although it smells nice, I'm sensitive to perfume and it makes me ill. 5) Although the wine tasting was lovely, the vineyard's bathrooms were not in working order - I had to choose between a toilet that was overflowed and a bathroom without a working sink. Also it would be nice if they pushed their products a bit more softly; buying the wine felt mandatory. I know I have a lot of recommendations, but really the tour was still fantastic. I appreciated our guide very much and we enjoyed our day immensely! Thank you.
Viola was an excellent guide...very informative and good natured. We enjoyed the farmhouse lunch and our visits to Siena and San Gimignano were excellent.
My sister and I had to leave the tour because she wasn’t feeling well. Our guide went above and beyond helping us to get a taxi and letting the taxi driver know where we needed to be taken. She was very kind and helpful. As for the tour, I can only speak about the first portion of the tour—to Siena. Our guide was very knowledgeable and provided a great deal of information.
This was an excellent tour that had an exceptionally knowledgeable guide - Regina and driver - Francesco. This tour was our favorite of the entire trip. We enjoyed ourselves immensely and learned a lot of history of Florence, Siena and San Gimignano. The “Tuscany Lunch” was outstanding. The food, wine and company all contributed to a true Tuscan Italian experience. Another positive aspect of this tour was the small size - only 6 people were in our group. The small number of people made it possible to interact more with the tour folks and further contributed to our enjoyment. I highly recommend.
Beautiful day and extremely fun! Definitely wish we would have had more time in san gimignano - was a bit rushed but otherwise a WONDERFUL tour!
Great tour! So nice to get out of the city and see the countryside! Food and wine were amazing
Viola was fantastic! We had a wonderful time!she made it very special with her incredible knowledge and charming personality.
The winery tour was fun but felt pressured to buy.
Great tour! Great guide! Love Walks of Italy!
The tour was lovely and a great way to explore Tuscany! In addition to the winery visit, it would be nice to have a pasta making class included so you can get a feel of local dish preparation.
Very enthusiastic guide who is also an artist!
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The trip was great! Eriza is a wonderful guide, full of energy and able to answer any question. Stefano was our driver, and he also gave us excellent information as he drove. It was a lovely day!
Tour guide was very knowledgeable about Italy and it’s history. We were given enough time to wander around in towns.
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Antonio did an amazing job on our Tuscany tour! We learned so much from him about each city we visited. Our driver was also very knowledgeable and helpful! This was a great tour!! I would recommend to anyone looking to tour Tuscany!
This was absolutely wonderful! Eriza was fantastic. Knowledgeable, friendly, and helpful. I absolutely loved the place we went to for lunch - the people there were so friendly and passionate about what they do. This was just a perfect day!
We had a fantastic day trip and enjoyed all the areas visited. Eriza was a great guide, her knowledge was extensive and she was very approachable. The time spent in each town was limited but the schedule was tight for one day.
Our tour was excellent as well as our guide!
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