Great Tuscany Tour and Guide Experience
sidarthw
Oct 6, 2026, 3:29:39 PM
Oct 6, 2026, 3:29:39 PM
Fantastic Tour. Alessandro, the tour guide, was knowledgeable and organized. We had a great time!!
About Activity
With this personalized tour of Tuscany, you and your friends may see all the area's hidden treasures in a single day. An experience made even better with an extravagant lunch and wine sampling in Tuscany.
We're going to leave in a cozy, air-conditioned minivan in the morning for a fast-paced tour.
In Siena, as you stroll through the alleyways adorned with Renaissance and medieval architecture, your guide will give you an insider's view of the first bank in history, the exquisitely designed Duomo, and the famous Piazza del Campo.
We'll take you to a family-run Chianti estate's vineyards for a laid-back wine-tasting experience and a superlative regional culinary experience while taking in the breathtaking scenery.
Then we'll drive you to San Gimignano, one of the area's greatest treasures and one of our favorite stops on this private tour.
The final stop will be Pisa, where you will have the chance to discover the Baptistery, the Cathedral, and the world-famous Leaning Tower!
What's Included
Includes
- Scenic drive to historic Pisa to explore its hidden corners and iconic tower
- Winery tour and wine tasting of four varieties
- Hearty farmhouse lunch – veggie and gluten-free options available
- Professional English speaking tour guide with you for the whole day
- Guided walking tour of Siena with entrance fee to the cathedral
- Visit the church and the museum of one of the contrade in Siena
- Travel by air-conditioned luxury van
- Free time to explore San Gimignano at your own pace
Excludes
Departure & Return
Departure Point
- Traveler pick up offered
Itinerary
Siena is a real medieval gem and in fact one of Tuscany's most famous and beautiful hill top towns. When you arrive you will join a 1 hour guided walking tour with a local city guide through Siena's most beautiful streets and sites, including the entrance to the Cathedral, a treasure chest of artworks. Afterwards, enjoy Siena at your own pace with free time for shopping or relaxing in an open-air cafe.
The first stop on the walking tour of Siena is a bank that has its headquarters in this square - the oldest surviving bank in the world. It's called Monte dei Paschi di Siena and it has been running continuously since 1472. Your guide will explain how Siena's wealth through the centuries came from being on the pilgrim route known as the Via Francigena, a route that led pilgrims between Rome and Northern Europe. Siena prospered as a banking town by lending money and exchanging money for the merchants who were using the pilgrim route as a safe travel route. The Sienese are still wealthy from their banking past and are still famous for their banks today!
Your local guide will then walk through some of the most picturesque back streets of Siena, while telling about something very unique to Siena are the 17 districts which make up the historical centre.The name for these ancient divisions is 'contrade'. Each contrada has its own symbol, normally that of an animal including a snail, rhino and giraffe amongst others. You will visit the church and museum of one of the contrade. The sense of identity and belonging to ones 'contrada' is extremely important. They are self-contained little worlds with their own church, where newborns are baptised, and a public fountain where the newborns are baptised a second time! Needless to say there are strong rivalries between these districts, that explodes during the Palio horserace held twice a year in Piazza del Campo.
Piazza del Campo is one of the most beautiful squares you will ever see and it is also the city's gathering place, where the locals meet for a coffee and to chat and of course gossip. The unusual square (actually not a square, it's in the shape of a sea-shell, and sloping!) is the site of the famous Palio horse-race. A 600 year old tradition of Siena. The piazza gets transformed into a racing track twice a year and the contrade, or neighbourhoods of the city battle out for the highest honour possible – winning the palio. You'll hear more about this on the tour, your local guide will set the scene so that you can somehow live for a moment the vibrant atmosphere of this incredible race.
Our walking tour then ends inside the Duomo of Siena – undoubtedly the jewel of the city. If you've seen the interior of Florence's Duomo, it is nowhere near as spectacular as Siena's. The most unique part of this city's cathedral is its floor. It's an artwork on its own, made out of the world's most precious marbles – in fact, it's a combined masterpiece of over 50 images created over 2 centuries by some of Italy's most important artists. Then, enjoy walking through the city center on your own before meeting your guide again to head to your next stop!
After the morning exploration of Siena, a 45-minute drive will take you the the next stop: Fattoria Poggio Alloro, an organic family-run wine estate – the highlight of the day! Enjoy an informal wine tasting lesson and a traditional Tuscan lunch with plenty of wine, in the most gorgeous location overlooking stunning views of the surrounding countryside. Take the opportunity to try fresh organic farm food of homemade pasta, cured meats (homemade prosciutto and salami), local cheeses, a real garden salad, and Tuscan biscotti. There is also the opportunity to buy the local products of the winery before heading to San Gimignano.
After lunch, a 15-minute drive will take you to San Gimignano, that is an even smaller, walled Tuscan hill town than Siena - about 6 times smaller - and a UNESCO World Heritage Site. San Gimignano is most famous for its towers of which there were 72 though there are just 14 remaining today. From this the city gets its nickname of the little Manhattan of Tuscany. Your guide will give you a map and point out the best landmarks, so that you can roam independently the picturesque streets and squares of this enchanting hilltop town.
Your guide will lead you to the entrance city gate and that is where the main boulevard starts from, Via San Giovanni. This street will take you to Piazza della Cisterna, the heart of San Gimignano and also the setting for several films. This was the square where festivals and tournaments took place while the Piazza Duomo was the religious and political centre. This is also where the best gelato in the world is – Gelateria della Piazza 'Dondoli'. It's won many awards as the best gelato, you could try it and see what you'll think!
From Piazza della Cisterna, the next piazza along is Piazza del Duomo – the Duomo, also known as the Collegiata, is small but is well worth visiting! The beautiful interior of the cathedral walls is filled with colorful 14th century frescoes in every space available. You could also climb up one of the medieval towers here in this piazza, next to the Duomo (the Torre Grossa) to appreciate the incredible 'BIRD'S EYE' view over San Gimignano.
Another stunning view over the towers of San Gimignano is from La Rocca. It is easily accessible behind the Duomo and It is a peaceful setting with olive trees and the wall surrounding the garden that formed part of the 14th-century fortress Medici of Florence built to protect this town from Siena. if you walk to the back of the garden and climb the steps to the top, the views over San Gimignano's skyline are absolutely breathtaking.
After the visit of San Gimignano, a 1 hour and an half scenic drive through iconic Tuscan countryside will take you to your final stop, Pisa.
Upon arrival, your guide will lead you straight to the famous Square of Miracles. At first sight, it is truly breathtaking - the white marble buildings glow in contrast to the perfect, green lawns. You will have about an hour to explore the Cathedral, Baptistry, Monumental Cemetery, and of course - The Leaning Tower!
During your time in Pisa, you can climb the Leaning Tower to admire the incredible views of the Square of Miracles from above. The views from the top of the Tower are truly breathtaking - from the monuments below, to the city surrounding the square, the Arno River, and the countryside in the distance... and part of the fun is also climbing the stairs inside the Leaning Tower that we will make you feel a bit dizzy at the end!
After leaving Pisa, it will take about an hour to return to Florence. You will dropped off at the start point with a camera full of pictures and a stomach full of hearty Tuscan food.
Language Offered
English - GUIDE
English - WRITTEN
Additional Info
Infants and small children can ride in a pram or stroller
Public transportation options are available nearby
Infants are required to sit on an adult’s lap
Not recommended for travelers with spinal injuries
Not recommended for travelers with poor cardiovascular health
Travelers should have at least a moderate level of physical fitness
Operated by Walkabout Florence Tours
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
Reviews
Lovely Day!
Coppell12
Sep 13, 2026, 12:47:28 PM
Sep 13, 2026, 12:47:28 PM
We had an amazing tour of the Tuscan countryside yesterday. Our guide, Alessandro, was terrific. He’s friendly and extremely knowledgeable. He was a pleasure overall. The stop in Siena was unforgettable. We had a local guide, Carlo, who was amazing. He was informative, outgoing and very passionate about his city. The lunch and wine tasting at Fattoria Poggio Alloro was exceptional. We enjoyed several excellent wines in a gorgeous setting. San Gimignano was up next. What a great spot for shopping and exploring. Finally, we got to see the tower of Pisa. Beautiful! Our driver was excellent as well. I absolutely recommend this tour to everyone!
The best Tuscany tour ever!
gildas387
Sep 11, 2026, 2:31:36 PM
Sep 11, 2026, 2:31:36 PM
What a wonderful experience! Our Walkabout Florence tour to Siena, San Gimignano, a Tuscan winery, and Pisa was truly one of the highlights of our trip to Italy. The entire day was extremely well organized, and Manolo was knowledgeable, friendly, enthusiastic, and attentive throughout the tour. Our driver Sergio was so profesional. We learned so much about the history, culture, architecture, and traditions of Tuscany while also having enough time to enjoy each destination. Siena was absolutely beautiful. San Gimignano was magical—walking through its medieval streets. One of our favorite parts of the day was the winery experience. The setting was beautiful, the wine was excellent, and the lunch was delicious. Ending the day in Pisa and finally seeing the Leaning Tower in person was the perfect conclusion to an already amazing day. It is a long and full day, but absolutely worth it. I fully recommend this tour!
An Unforgettable Day in Tuscany with Alessandro! ⭐️⭐️⭐️⭐️⭐️
lpb127
Jul 27, 2026, 5:56:00 PM
Jul 27, 2026, 5:56:00 PM
We had the most incredible private tour of Tuscany with Alessandro! From start to finish, he was extremely knowledgeable, helpful, and genuinely so much fun to spend the day with. We had a large group of 11 kids and 8 adults, and Alessandro did an amazing job making the experience enjoyable for absolutely everyone. He kept the kids entertained while also teaching the adults so much about the history, culture, food, and wine of Tuscany. You could really tell how passionate and knowledgeable he is about the area. We visited two gorgeous wineries, both of which were absolutely amazing, and had the opportunity to experience the beauty and charm of San Gimignano. Each stop was special, and Alessandro made everything feel effortless and enjoyable. On our way back to Florence, he also arranged for us to stop in Pisa, which was the perfect way to end an already fantastic day. Seeing the Leaning Tower in person was such a memorable bonus! Alessandro went above and beyond to make sure our entire group had a wonderful time. He was incredibly accommodating, personable, and full of great information. We learned so much while having an absolute blast. If you’re looking for a private Tuscany tour, I highly recommend Alessandro! He made our day unforgettable, and we couldn’t have asked for a better guide. 🇮🇹🍷❤️
Fun tour guide and very fun experience
FarAway17832543498
Jan 25, 2026, 12:21:33 PM
Jan 25, 2026, 12:21:33 PM
leaning tower of pisa was awsome. great time david was a great tour guide!!
A Fun-Filled Memorable Day Visiting 3 Italian Cities and a Winery
Y6133RTmelissab
Oct 22, 2025, 4:01:26 PM
Oct 22, 2025, 4:01:26 PM
Manolo was a fantastic tour guide and Ali an excellent driver for our day long trip from Florence to Siena, Vecchio Maneggio Agriturismo, San Gimignano and Pisa. Mano is absolutely great at what he does!
We had an amazing day...
Sarah_M
Oct 11, 2025, 6:39:44 PM
Oct 11, 2025, 6:39:44 PM
We had an amazing day with Alessandro today as our private tour guide. We learned so much about Italy’s history and saw the most beautiful cathedrals. The farm with wine tasting was a highlight and they are able to accommodate for dietary restrictions if needed. So far this was our favorite day in Italy! I would definitely recommend this tour!
Fantastic Journey through Tuscany
kimkP6759MN
Jul 13, 2025, 2:05:14 AM
Jul 13, 2025, 2:05:14 AM
What an absolute fabulous tour. Gabriel was an excellent guide and how Labi got the bus through all those tiny roads is beyond me! The farm house lunch alone would have made the trip worthwhile but adding Siena, San G and Pisa was icing on the cake.
Amazing Day Tour
151pate
Jul 3, 2025, 11:28:09 AM
Jul 3, 2025, 11:28:09 AM
We had an amazing day tour traveling to these three cities, it was planned out perfectly. Antonio (toni) was a perfect tour guide for our family, very knowledgeable but also very good personality. Flexible to our needs. We had a great local guide in Siena that highlighted the city, had the Worlds Best Gelato in San Gimignano, and our lunch at a Tuscan winery included our favorite pasta dish of our trip, the bolognese. Pisa was planned as a short stop to see the Tower, and that really is enough time and all you need to see here. I would give this more than 5 stars if I could, highly recommend.
An exceptional 12 hours seeing wonders of Tuscany
susanraws0n
Jun 16, 2025, 9:17:43 AM
Jun 16, 2025, 9:17:43 AM
The day started off on a very warm morning, our guide Claudia was an absolute dream, she looked after everyone and ensured we all enjoyed an unforgettable day. Cold water available on the coach for 1 Euro was very welcome especially as temperatures reached 38 degrees! Also the air conditioning was first class, again very welcome after being out walking. Claudia spoke to each individual person on the coach, she's a lovely person and very experienced in her knowledge. Maps with information were given to each person and were very interesting to read. We were given local information on each place we stopped at and advice given on some must do places to visit.Siena was an amazing place to visit, the history of the famous Palio horserace, still run today, was so very interesting. The beautiful Duomo of Siena is awesome, several works of art on view but I felt the floor was the highlight of the cathedral, it is made of individual inlaid marble and took 200 years to complete, a memory that will stay in my mind forever. Our lunch at a picturesque winery was delicious, local cheeses, cold meat, a pasta ragu and copius amounts of red and white wine made from their own grapes from the winery was absolutely lovely. On to our next stop, Pisa, everyone was very friendly and chatting to each other on the coach, Claudia put a dvd of the famous Palio horserace which was enthralling. Seeing the leaning tower of Pisa and actually climbing the 255 marble steps to the bell tower was an unforgettable experience, the views from the top were magnificent. Back to the coach and our journey back to our meeting point in Florence was a time to reflect on all the wonders we had seen, it felt like we had time travelled as we had seen so much in one day, it was the best 12 hours I have had for a very long time and full credit goes to Claudia our guide for the day along with the skilful driving of Domenico our driver. Thank you Walkabout tours.
Sampler of Tuscany
Excursion744950
May 8, 2025, 1:55:40 PM
May 8, 2025, 1:55:40 PM
Wonderful tour. We spent the day with our Amazing guide Mirella. Mirella provided humor and knowledge of the regions. Highly recommend this full day out in Tuscany.
The Best of Tuscany Tour….thoroughly enjoyable!
917jilliann
Apr 17, 2025, 12:22:43 PM
Apr 17, 2025, 12:22:43 PM
Had a wonderful Tuscany tour with the very entertaining and caring Gabriel and excellent coach driver Emiliano who work very well together with such a big day for them both. Views from San Gimignano Torre Grossa tower are spectacular, lunch and wine at the organic farm vineyard were delicious and we thoroughly enjoyed Siena and Pisa too. We highly recommend this tour.
Fantastic Tuscany Experience
I2911KKdawnc
Apr 11, 2025, 8:34:38 AM
Apr 11, 2025, 8:34:38 AM
Tour was very well organised, the meeting point was easy to find, our tour guide was waiting there for us with a Walkabout board, about eight minute walk from meeting point to where coach was waiting for us. Our tour guide Manolo was amazing really good English and very knowledgeable about Tuscany and Italy in general, great knowledge of the history of the area and key dates, always happy to answer questions, with a great sense of humour. We had an additional local guide in Siena who was equally knowledgeable and friendly, lots of interesting of the beaten track facts as well as the important things you would want to know. Delicious lunch at the winery with friendly people serving us and plenty of wine, so delicious we bought some to drink back at our hotel, very reasonably priced. San Gimignano was a beautiful medival city where all of the time there was our own free time to explore at our own pace, had a gelato from Gelateria Dondoli recommended by Manolo which was the best gelato we have ever tasted. Pisa was unfortunately wet when we arrived but that didn't detract from one of the best tour experiences we have ever had. Our coach driver was also amazing great smooth ride in a very comfortable coach. Thank you Manolo and Walkabout Tours.
Bespoke day in Tuscany!
Laurie L
Mar 29, 2025, 8:55:52 AM
Mar 29, 2025, 8:55:52 AM
Very special day with Davide and our driver! I wanted my husband to experience a bit of Tuscany outside of Florence. Our day started in Sienna with an incredible local guide who knew all of Sienna’s history and guided us to the places we wanted to see. We then went to Fattoria Poggio Alloro winery for a Tuscan lunch and wine tasting that was scrumptious and a view of San Gimingano that was spectacular. Next we headed into San Gimingano for a little shopping and champion Gelato! Our last stop was Pisa for the stunning views from the tower. Davide was knowledgeable, engaging and super fun to travel with! I highly recommend this tour.
Best tour EVER!
sabrinasZ2805JF
Sep 29, 2024, 3:35:46 AM
Sep 29, 2024, 3:35:46 AM
Nado and Tony were very personable, knowledgeable, and made it very entertaining for us on a very long day that allowed us to really have an authentic experience! I would highly recommend them to anyone!
Florence, pizza,San Gimignano, Siena!!!
A6724ULanthonyc
Jun 22, 2024, 1:57:06 PM
Jun 22, 2024, 1:57:06 PM
We had a FANTASTIC time learning about the Italian history. Tony, was fantastic and offered a lot to the experience! A trip of a lifetime for our family!
Good food. On time. All important places covered. Insights included historical and contemporary issues.
Climber40671980413
Jun 2, 2024, 11:43:33 AM
Jun 2, 2024, 11:43:33 AM
The tour guide Victoria was very experienced and kind. Winery Lunch was excellent with good choice of wines and food. Enough time was provided in all places. Amazing trip.
Excellent
Curiosity61233589537
May 13, 2024, 3:48:46 AM
May 13, 2024, 3:48:46 AM
Excellent tour, Siena, San Gimigniano and Piza. Panoramic view, excellent food and wine at a toscany biologigal farm. Our guide Antonio was superb !
Breathtaking Tuscany!
S6437ADchrisk
Apr 23, 2024, 12:52:02 PM
Apr 23, 2024, 12:52:02 PM
Absolutely wonderful trip! Sara, our guide, was so full of knowledge and history! I felt like I was living in the story as she shared it with us! She never rushed us, always encouraged us to ask questions, and took us to an amazing place for lunch! I would love to do this tour again! Luca the driver did an excellent job navigating and such a gentleman! Make your trip to Italy, book this trip! Ask for Sara!
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