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 615 Customer Reviews

our guide ?eliza was wonderful! she was relaxed and really seemed to enjoy sharing sienna and Tuscany with us
Sandra was an exceptional tour guide. She was very knowledgeable of every area that we toured and was most enthusiastic. She made the tour a wonderful experience.
This tour was very well put together and was a great way to see the different parts of Tuscany in one day!

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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Florence Food Tour
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Uffizi Tour & Tickets
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Florence Duomo & Accademia
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our guide ?eliza was wonderful! she was relaxed and really seemed to enjoy sharing sienna and Tuscany with us
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Sandra was an exceptional tour guide. She was very knowledgeable of every area that we toured and was most enthusiastic. She made the tour a wonderful experience.
This tour was very well put together and was a great way to see the different parts of Tuscany in one day!
Very enjoyable tour even though it was on one of the hottest days of our trip. Gorgeous scenery and sites and we really enjoyed Sandra's informative commentary.
My family could not stop talking about their experience with the Walks of Italy tour! My husband has been experiencing leg pain recently and was worried about being able to enjoy the tour. The guide (believe his name was Nebo) did an exceptional job of accommodating by making sure there were places for my husband to sit and not have to move around too much at any given time while still having the full experience. The day was filled with interesting facts and the guide made everyone feel comfortable and relaxed while learning so much about the places they visited. We did another tour later in the week because my daughter and I were delayed in getting to Florence and it was a good tour but the rest of the family said there was no comparison to the Walks of Italy tour in terms of the guide, driver and how the day was planned out for those attending (we wanted to only do a half day and still get in a wine tasting outside of Florence and could not find one on your tour list which is the only reason we went with another company). I cannot thank you enough for the experience you gave my family. I look forward to our next trip abroad when we can all enjoy another tour with Walks of Italy!! Best regards, Caroline Clark
Incredible guide!!!!!
The tour was really great, we got to see a lot. Our guide was very informative.
Greta was the perfect guide for our day, she is very knowledgeable and a asset to your company. the day was well planned , the lunch was very enjoyable with Greta and our other tour members. we wouldn't hesitate to recommend Walks of Italy to our friends.
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We enjoyed the tour very much. It was informative and interesting. There was ample time to spend on our own and take pictures. The sites were things we wanted to see. The driver was friendly and provided commentary when the guide was in the other car.
Driver blandi was also excellent. Very professional and was a good safe driver. Nebo was knowledgeable and made the tour interesting and fun for everyone. Highly recommend the tour to anyone Lunch and winery visit were fantastic No issues with the tour but I am checking the box because there is a slight issue with our billing price (we were told that a 25% discount would be honored. I've sent the information to Gaia already)
Lunch at winery was the highlight. Beautiful setting, engaging sommelier, and absolutely delicious (and plentiful) food and wine.
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our tour guide was very enjoyable and the day was wonderful. thank you!
Greta, our guide, was fantastic! One of the best we’ve ever had. Siena is high on our list of cities we hope to visit again. The wine tasting and lunch was so much fun. We expected great wines, but the food was surprisingly excellent.
Both the guide and the driver were fabulous. They knew a lot about the area and were very enthusiastic. They constantly checked in with us throughout the day to ensure that we were all having a good time. This tour was one of the highlights of my Italy trip.
Excellent tour!
The wine tour was amazing!! Would highly recommend this tour!!!
Our guide was excellent! He was passionate about helping our group get the most out out of our visit. He clearly loves his job and is very knowledgable about the history that shaped Florence.
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The tour was fantastic, appropriate time to visit both Sienna and San Gimigniano . lovely visit to Vineyard and lunch . I would highly recommend it . from the comfortable van ride on, it was the perfect day. thank you
She was enthusiastic and personable. I wish the guide provided longer walking tours in Siena and San Gimignano to those who wanted rather than giving us free time without much guidance. Alternatively, she could have given us some instructions as to where to go during free time.
We had a wonderful day with our guide Sandra who gave us so much information about Tuscany and each place we stopped. The travel was very comfortable and each stop was well organized. The lunch was fantastic and in such a beautiful setting and of course the wines were amazing. Finishing out in San Gimignano with ample time to shop rounded out a perfect day. We highly recommend this tour!
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Fantastic day out. We would probably opt for a tour without San Gimignano next time. Personal opinion - we were ready to head back to Florence after the lovely lunch - we were tired.
We LOVED this tour! Everything about it was great - the food, the wine, and Eriza! She gave us so much information and really helped us enjoy the experience. I'd also like to acknowlege our wonderful van driver Guiseppe! He was funny, friendly, and very helpful.
Excellent tour, the whole experience and good to get some free time also to explore.
It was fantastic. We had a great day!
The trip went well. It would have better if we had Valentina the whole day instead of alternating her between the 2 vans. It would have been nicer also if we could have stopped to take photos on one of the cypress lined vineyards you see on the post cards but overall it was a great experience.
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Overall, very good. We enjoyed San Gimignano the best.
Nebo was great! He was a very knowledgeable tour guide and we were very pleased with the entire day of touring.
Neybo was great, he was very knowledgeable and patient. His calm demeanor gave us a great relaxing day. Even brought us up to his personal relaxation spot to view San Gimignano from the tower.
Eriza was professional and personable. She provided pertinent information as well as interesting anecdotes. Since our tour was on a Sunday, the Siena cathedral was supposed to be closed; however, upon our arrival, Eriza realized that it was actually open due to the Palio did Siena being held the following day. She quickly got us entrance tickets, so we were able to tour the inside of the cathedral which was something that we had wanted to see. Thanks to Eriza and our driver, Luca, we thoroughly enjoyed our day in Chianti, Siena and San Gimignano.
We are totally satisfied with the tour. All was organized well. The guide was knowledgeable and a sencerely friendly personality (which is not that often among guides by the way). Most of all we liked the winery. That was a special one: run at the very high standards and with the creative approach (collaboration with local artists, etc), not the ordinary one. We only felt that we could spend an hour more in Siena, but that would make the whole tour one hour longer, so more tiresome in the end of the day...
What a wonderful way to spend a day! It's not hard to understand why everyone who visits Tuscany wants to return over and over. The views are breathtaking, the food beyond compare and the wine....ah...perfecto! Our guide made everything go smoothly and our driver, Blendi, was a delight to be with. The wine tasting and meal were fantastic.
The whole tour was fun, professional and informative from pick up to drop off! Our driver Stefano was very professional and friendly and couldn’t have asked for a better guide than Irizi ( sorry if incorrect)
Loved our day trip and would highly recommend it and your tour company!
This was my first time on a tour like this (a driven day trip), although I had already been on a couple of "context tours". I enjoyed the tour, all of the places that we went were interesting and scenic. I climbed the tower in San Gimignano and got some great pictures. The winery lunch and wine tasting was both delicious and interesting. I was not sure what to expect about history and perspective from this tour but I felt that there could have been more discussion of history of Siena.
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Nebos was an excellent guide and very informative with historic and local facts of all places visited. He gave great tips on what to see in each cathedral as well as how to get a clean restroom....the trip was great and we will definitely be using Walksofitaly with anything we get the opportunity of doing again. Pleasant and just overall a great time....thank you from this first time visitor to Italy! Sherry Anghel
Our guide Nebo was informative as well as humourous. We could not have wished for more. We even had time for a sleep on the way home. We also felt very safe with Marco our driver!
Thank you.