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 719 Customer Reviews

Wonderful tour! Winery was lovely and tour guide was knowledgeable and personal.
Was amazing experience and the people was so Nice. A great tour! Super organized. Perfect
Laura was the perfect guide with her knowledge and welcoming conversations. This event was one of the highlights of our trip. The small group atmosphere felt more like saying bye to friends at the end. Beautiful Tuscan winery and host

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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Wonderful tour! Winery was lovely and tour guide was knowledgeable and personal.
Ismael and Francesco were so lovely, warm, kind , funny and informative. We had a great day, and even though the weather was terrible we still enjoyed ourselves immensely. We also took the food tour on Saturday 1 December. I’m afraid I can’t remember our guide’s name but he was charming and extremely interesting. The tour was so much more than simply experiencing food. The two tours we took made our stay in Florence really special. We wouldn’t hesitate in booking with you again. Thank you.
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Was amazing experience and the people was so Nice. A great tour! Super organized. Perfect
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Laura was the perfect guide with her knowledge and welcoming conversations. This event was one of the highlights of our trip. The small group atmosphere felt more like saying bye to friends at the end. Beautiful Tuscan winery and host
Greta was wonderful on the 8h day trip to Tuscany. Mixing history of Florence and the area with great guided tours of beautiful Siena and San Gimignano. She was very personable and understandable. The Chianti lunch and wine tasting were top notch!
Greta, our tour guide, was fantastic! Our driver was really fun also!
Nebo is an incredible asset to Walks of Italy! He was extremely knowledgeable, friendly, and seemed great at making sure everyone’s interests were served. The sights were amazing, and the lunch and wine tour were great as well.
Our guide, Nebo ( I hope I spelled that right), was quite good. He seemed interested in the information he was sharing and was very personable. We loved the farm house, and enjoyed the cathedral. We were there for one of the worst storms you all have had in a while, but we still enjoyed ourselves!
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Greta is an amazing tour guide. Extremely knowledgeable and understandable. It was an unforgettable tour.
We loved this tour we had 2 weeks in Italy and booked 7 tours in total. Well done !!!!
This tour was spectacular! Absolutely not-to-be-missed!
The tours were excellent. Our guides were knowledgeable and engaging. We bought the package which included the Uffizi museum and then also went on wine tasting in Tuscany. It was worth every penny.
Excellent day all around!
The trip was fantastic. We loved Siena and seeing the countryside. The opportunity was just what we were looking for.
Greta did a wonderful job explaining the sites being visited and was a pleasure to spend the day with. While we loved everywhere we visited, in our opinion it would have been nice to visit only one of the areas along with the winery tour. That would have left more time to explore in either of the locations. The winery tour was a wonderful as expected.
Eleanora was fantastic - she was so kind, funny and informative! Everything about the tour was wonderful!! We will recommend this tour to anyone visiting Florence/Tuscany and plan to use Walks of Italy for future trips!
Thank you for a fantastic tour with the best tour guide ever! Laura is very knowledgeable and has a great personality. She answered all questions from the group and all of my questions. We had a great time and Laura made the trip a great experience. I had said to my wife before the tour that we need to rent a car to get out to the Tuscany region, but the tour satisfied my desire and some. PERFECTO! THANK YOU, THANK YOU.
Great tour guide, very knowledgeable and personable. Patient with group members of all ages. The tour was wonderful, such amazing sites. The lunch was a great location with amazing food and wine and generous portions of both.
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Everything about this tour was wonderful. The sights we saw, Laura’s knowledge, the organization, and the food and wine. Would definitely recommend it!
Excellent and informative tour overall, with great guide, efficient use of the time we had, and we loved the visit to the winery with tasting and delicious lunch. Highly recommend this tour!
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This was a terrific trip. Everything was wonderful. I particularly thought the guide was fabulous and informative. She made the trip really special and I would highly recommend her and the trip to everyone. The driver was courteous and prompt. The scenery was wonderful. The winery visit and lunch were superb.
Perfect day! Eriza was a great guide.
The tour exceeded our expectations . The itinerary was wonderful with the visits to the different towns and the lunch in the Chianti region. Good balance of group time and free time. We appreciated the small group size. The tour guide was informative, engaging and enthusiastic - he was terrific. We will definitely consider your tours again and will recommend to friends. Thank you, Linda Meyers and Richard Handler
Eriza was an outstanding guide-knowledgeable,personable and professional. Loved the timing of each stop. Lunch at the winery with wine tasting was fun. Would also like to add that the driver was very professional and smooth. We will use your company again!
WONDERFUL. Best part of my trip. Guide was fantastic. Perfect balance of activity in the time allotted. Excellent wine tasting and lunch. Will definitely book another tour with the 'walks' company.
Eleonora was an absolute delight! Her pride in the history and culture of Italy, and her joy in sharing this with us was such a pleasure. She even bought us her favorite cookies at a bakery in Sienna to try. What a gem she is, and what a wonderful day this was! The lunch and wine tasting at the vineyard was delicious, and the wine steward shared information clearly and enthusiastically. Highly recommend this tour!
Eriza was fantastic! This was our favorite day on our vacation. Tour was amazing. (2nd favorite day was our other Walks Colosseum tour!)
Overall the tour was fantastic. Would have liked a bit more free time in Siena at something other than the bakery and cafe. As they were preparing for the Palio, we really couldn’t spend time in the center of town. The guide was quite informative and we were provided with an enormous amount of information. Would highly recommend.
Would like the option of paying for larger church ticket that would include the lookout and baptistery since you are given the time to look around. There was no time to wait in the line and pay again for a church combo ticket, so instead we just wandered around town.
Wonderful day- Siena is delightful and the Duomo more spectacular inside than that in Florence. Lunch at the winery/olive farm was out standing and plentiful. Guide and drivers worked seamlessly together and the countryside was truly gorgeous. Another home run with walks of Italy ( our day trip to the Amalfi Coast was also the other highlight of our trip).
The tour was recommended by a friend. We enjoyed it very much, it was our favorite activity during our 2 week trip to Italy and Spain. Eriza was delightful, I enjoyed hearing all the history of the area and her knowledge about wine. Lorenzo at the winery was also great. Very well organized, great sights, a memorable day!
This tour/experience was amazing! Viola was very knowledgeable and friendly. I felt like she was a part of my family. The lunch and wine tasting were incredible. I also loved that we got free time in each of the towns. I would recommend this tour to anyone.
Wonderful guide, really great attitude and lots of knowledge. Great tour, would thoroughly recommend. Could only be improved with a tour of the Duomo in Sienna.
Francesca was sweet, informative, patient, and alot of fun. Simone, our driver was awesome as well!
Best tour we had during our 2Weeks in Italy. This a must do tour. Highly recommend this tour Guide was GREAT
My husband and I really enjoyed the day trip. We were in the van without our guide, Sandra. I would have liked a little more information regarding the history and culture of the region. The meal at the winery was very good as was the brief tour. The wine tastings were generous. I'm wondering how you compare to the trips advertised in the hotel brochure that were 98 euros as opposed to our trip that was more costly. Thank you for a very nice experience.
Sandra was very entertaining and knowledgeable. Very pleasant day
We so enjoyed our delightful tour of some of the charming areas in Tuscany. Eriza was informative and fun and did an excellent job educating us about each stop in the tour. Our host at the vineyard was very funny and entertaining! Lunch was amazing and delicious. Traveling in the minivans was comfortable and we felt very safe. We also enjoyed spending time with the other guests on the tour. We would definitely recommend this tour to our friends and family. Ciao! Kittie Yohe ❤️
We thoroughly enjoyed our tour. We do not like large tour groups and found the group size of Walks of Italy very appealing. Since they use vans, instead of a bus, they were able to get into the centers of Siena and San Gimingnano. Our tour began with a meeting at a convenient location, where we were assigned our guide and vehicle. We had a total of six guests in our van. Our guide (Viola) covered two vans, so our tour group was a total of 12. She alternated between the two vans during the drives. Both she and Alessandro (our driver) were very friendly. She was a fantastic guide and provided much information about the sites we visited, as well as the surrounding area. The tours of Siena and San Gimignano were very well done. We had been to both cities in the past, but learned and saw new things. Finally, the lunch in Chianti was excellent and the wine was plentiful. They accommodated the vegetarian preference of my wife and myself without any hesitation. We highly recommend the Walks of Italy Tuscany Day Trip if you are in the area and looking for a unique experience.
Our guide was knowledgeable, passionate and entertaining. It was impossible not to have a fabulous day. Our driver was also wonderful.
BEAT tour guide and best tour we have had in Italy!!! Used a couple other tour companies and Walks of Italy has hands down been the best with the TOTAL experience! On time, EXACTLY as described, very knowledgable guides and outstanding attractions. Eleonora was delightful and went above and beyond to assure we all had an exceptional experience!!! THANK YOU!
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