Walks of Italy

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 483 Customer Reviews

A completely amazing experience and I would definitely do this tour again!!
A great tour. Our guide was very prompt and communicative.
Best tour/tour guide! Thank you

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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A completely amazing experience and I would definitely do this tour again!!
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A great tour. Our guide was very prompt and communicative.
Best tour/tour guide! Thank you
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Fabulous day trip from Florence. Our guide had no trouble keeping everyone informed during our drives as he shuttled between minivans. Everything about the tour was perfect.
We felt a little too rushed in Sienna and San Gimignano. An extra 30 minutes in each location would have gone a long way in feeling like we had enough time to explore the towns and shop a little bit. We otherwise were too worried we wouldn’t be back to the meeting point in time. Otherwise, our guide and driver were both excellent, and the experience was overall fantastic.
This was a wonderful day trip. Everything we expected and more. Our guide Noshi (hope I have that spelling correct) was extremely knowledgeable and enthusiastic. We hope to have him again on another walk. Outstanding !!! and Thanks!!!
We had a very nice guide , Anna, and a very nice driver as well! We had 6 people on our tour and it was quite enjoyable to see beautiful Tuscany in a minivan. We will recommend and use Walks of Italy again, thank you!!
It was a wonderful day and both the driver and guide were professional, friend and knowledgable. Loved that it was such a small group (5). This made it more intimate and I think everyone gained more from the day. Great winery!
Fun Full Day!!! Awesome experience at the Winery and Lunch was excellent!!
Excellent and informative. Great lunch and wine tasting with three of our group of 6 accommodated as vegetarians. Much wine and food included in the price, much more than expected. Laura was great!
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An absolutely beautiful tour brilliantly planned out to spend time in each place at the best time of day for each city. I loved it and would do it again on my next trip to Florence!
Loved every moment of the tour. The small group was excellent, and would've hated having a bigger group. Anna and the driver were so friendly, and knowledgable about the area and more. At the end of the tour and once they dropped us off I felt like they were wanting a tip by hand movements and more.
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Driver and guide were both friendly, knowledgeable and helpful. They seemed genuinely interested in making sure we had a good experience.
My husband and I had an amazing time on this tour. It was a fun and beautiful day! Claudia was wonderful! Highly recommend this tour.
A great tour, different than the others. Anna was wonderful and a joy to spend the day with. Siena was fantastic and traveling to San Gimignano was much more interesting that I originally thought it would be. We look forward to using Walks of Italy on future travel.
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Claudia was the best! It was a very relaxing and beautiful day! We would do it again.
Claudia was an excellent guide - knowledgeable, engaging, personable, gun.
Our guide Claudia was fun, the countryside and towns were so charming, and the food at the winery was absolutely delicious. A wonderful trip. I would just recommend a stop for a few minutes so we could take photos of the breathtaking scenery. It was a wonderful day.
San Gimignano was lovely! The food and wine was also great
Anna was fantastic. She really gave us all her energy in describing the sights, giving us historical background and keeping us on track while still allowing us some freedom for photos, coffe, etc. We loved the beautiful places we visited as well as the delicious winery lunch and tasting. It was a lovely day all around. We also enjoyed the small group of people who shared the tour with us.
Lovely day and Claudia was a wonderful guide!
Maria Guilia was a great guide. Not only did she explain what we were seeing, she gave us insights to how the locals lived and viewed their towns. In addition, the wine tasting at the farm in Chianti was excellent. We normally do not like red wines, but these wines changed our minds about red wines. We also got to experience having olive oil that was made the previous day. In our two week stay in Italy with a tour almost every day, this was our favorite tour.
Great tour, lots of information and fun!
Gulia was great! Very personable, informative as well as entertaining. This tour was the highlight of our trip! We loved seeing Siena, San Gimgiagno and having lunch at winery/olive farm. I loved learning about all of the wines and the lunch was delicious! I would book another tour through Walks of Italy when I plan to go back. ( Hopefully sooner than later) They money was well spent and the memories will last a lifetime. Thank you Gulia!!!
We had a wonderful time!!! Only thing I would consider changing would be to add another 30 minutes or more in Siena for some wandering or shopping. Thank you!
We loved Eleanora and the day trip from Tuscany. It was certainly a highlight of our time in Italy! Eleanora is fantastic and knows her history!!
Everything was wonderful. Our guide was excellent. She is a jewel. Thank you.
Would have liked a bit more free time in San Gimignano but laura was lovely!
Anna was the best guide ever! She was delightful and informative the entire time. Thank you, the Youngblood and Caldwell Families
The day was perfect and well planned. The tour guide and driver could not have been more helpful. Would highly recommend.
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Great trip! No complaints!
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The only negative was the quality of the lunch at the vineyard. We expected a lunch with a wow factor given the event price.
Excellent tour. Enjoyed the lunch at the winery. Gulia our guide and Marco or driver were fountains of information. The highlight was the cathedral in Siena.
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I do not give a 5 star rating for this tour for the reasons detailed below but I had a great time. Our guide (Claudia if I remember well her name) was a very kind and attentive person, passionate by her country. I felt like I knew her for a long time. She did a great job and I felt sad to leave her at the end f the day. Our driver was very professionnal and a nice person. The bus was very confortable. The tour itself was fine, however I felt that a better balance should be reached between the visits, for which I paid more than $200, and the commercial "attractions". For instance in Siena, I would have liked to have more time for visiting the cathedral and the city, than the candy shop on the main square (although they are greta candies and are worth a short visit). The lunch time was an amazing moment. The people was friendly, the food and wine were absolutely devine. But the lunch lasted about 3 hours, which is a bit too long since people are invited to test the wines with the objective to buy wine bottles for exportation. Finally, the visit of San Gimignano was not a visit per se, since we add one free hour by our own to go through the village which is full of shops. I would have preferred a guided tour with more explanations about the history of the place and the architecture. Once again. I felt that I was blessed to live this experience I will recommend your company with no hesitation.
This was our second Tour with Walks of Italy for the Chianti and Sienna/San Gimignano Tour. My husband and I did this one last year. It was our favorite day in Italy, and we were just as excited to do it this year with our family. Anna was our host, she is delightful and knowledgeable, and Stefano, our driver, made me feel safe and comfortable on the drive. Poggio Amorelli served us a delicious lunch and even prepared special vegetarian dishes for me and my husband. Lorenzo hosted us, and was kind and interesting. We hope we can take this tour again next year! Sincerely, AnneMarie Pisano
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