We booked this tour because we wanted to use Florence as a base to explore Tuscany, but what we didn’t expect was that the people leading the tour would become the highlight of the entire experience. Our family of five spent the day visiting Siena, San Gimignano, and Pisa with Alessandro as our guide and Gaspare as our driver. They were an outstanding team. From the moment we arrived, Alessandro impressed us with his professionalism, organization, and genuine care for every person on the bus. Safety was always a priority, but what made him exceptional was how much he shared about what it truly means to be Italian. Instead of simply reciting facts, he brought Italy to life through personal stories, history, culture, traditions, and even the origins of common stereotypes—explaining which ones hold some truth and which don’t. By the end of the day, we felt like we understood Italy in a way we never could have by simply visiting these beautiful places on our own. What stood out most was how personal he made the experience. Large bus tours can sometimes make you feel like you’re just being moved from stop to stop, but Alessandro made sure every guest felt seen, welcomed, and engaged. Whether he was speaking to the whole group or having individual conversations, you could tell he genuinely cared that everyone had an unforgettable day. A special thank you to Gaspare, whose calm professionalism and expert driving made us feel completely safe and comfortable on the winding Tuscan roads. You could tell the teamwork between him and Alessandro came from years of experience, and it made the entire day run seamlessly. We’ve taken many tours around the world, and this was one of the very best—not just because of the incredible destinations, but because of the people leading it. Thank you, Alessandro and Gaspare, for giving our family memories we’ll treasure for a lifetime.
About Activity
What's Included
Includes
- Winery tour and wine tasting of four varieties only for 18+ age old
- 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
- Air-conditioned vehicle
- Visit the church and the museum of one of the contrade in Siena
- Free time to explore San Gimignano at your own pace
Excludes
- Gratuities
Departure & Return
Departure Point
- Traveler pick up offered
Itinerary
After meeting your expert guide, an air-conditioned minivan will whisk you away to the first stop of the day, Siena. The drive to Siena will take about 1 hour and 15 minutes.. During the journey, your guide will explain the itinerary for the day and entertain you with interesting facts about Siena and Tuscany!!!
After lunch, a 45-minute drive will take you to Siena, 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'. You will visit a church and museum of one contrada. Each contrada has its own symbol, normally that of an animal including a snail, rhino and giraffe amongst others. 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!
After the morning exploration of Siena, a 15-minute drive will take you the the next stop: Fattoria Poggio Alloro, an organic family-run wine estate – the highlight of the day! Visit the farm, 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 meet fellow travelers while feasting on 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.
San Gimignano is a small, walled Tuscan hill town 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 drive will take you back to Florence. You will dropped off at the start point with a camera full of pictures, a stomach full of hearty Tuscan food and a host of new friends.
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Reviews
This day trip from Florence ended up being one of the highlights of our entire Italy vacation. Despite being a full-day excursion, it never felt rushed or exhausting. The itinerary was well organized, the transportation was comfortable, and everything ran smoothly from start to finish. Our guide, Manolo, was outstanding—friendly, engaging, funny, and incredibly knowledgeable. He kept the group entertained throughout the day while sharing interesting history and local insights. The driver did an excellent job navigating the winding Tuscan roads, allowing everyone to relax and enjoy the scenery. The winery stop was wonderful. The food was delicious, the wine tasting was excellent, and we enjoyed it so much that we purchased two bottles of wine, a bottle of olive oil, and balsamic vinegar to bring home. San Gimignano- we wandered off the main streets, explored some quieter areas, and captured some of the most beautiful countryside photos of our trip. We also visited the illusion museum, which was a fun and unexpected addition to the day. Siena was stunning, Pisa was exactly what you hope it will be, and the drive through the Tuscan countryside was breathtaking. Every stop offered something unique, and there was enough free time to explore without feeling rushed. If you’re staying in Florence and want to see several iconic Tuscan destinations in one day, this tour is an excellent value and an unforgettable experience. Highly recommended! 🇮🇹🍷🍇📸✨
We loved all the places we visited!! Our tour guide Mano was the best!!! A very recommended tour if you are in Florence. The bus was very comfortable and our driver very good. All the places we visited were lovely!!! San Gimaniano is incredible!!! Pisa was perfect!!! And Siena OMG what a City!!! Perfect way to see them all!!!
Luca was amazing! We learned so much history and had fun exploring Sienna, San Gimignano and Pisa! Would definitely recommend for a day trip :)
El tour fue excelente! Emma, our guide, very nice, with very good explanations and excellent recommendations throught the tour. And Giuseppe … la creme de la creme !!
Walkabout Tours is the best! I had a custom tour for my high school group which included teachers and students. What a wonderful experience! We started in the beautiful town of San Gimignano, stopped for a superb lunch at a nearby winery and then continued on to Siena. The group had an amazing time! Our guide for the day was Manolo and he was top notch! He was full of historical facts. He was fun, very considerate, had a good sense of humor and he was very professional. Everyone enjoyed his presentation. Everything ran perfectly on schedule and Manolo managed the tour schedule well. He was very conscientious of every detail and he went well above and beyond our expectations! The entire day was a wonderful experience--one our group will never forget!
Our guides Alex and Eliana were outstanding! The whole day was a wonderfully romantic and informative experience. The perfect balance of history, guided tour, and on our own time. The winery was gorgeous, the tasting more than generous, and the food was excellent. I would highly recommend this tour to anyone who wants to experience the Tuscany countryside, learn some history, and have lunch at an amazing winery with some of the best wine made!
I found Walkabout tours after doing extensive research to find the best private tour in Tuscany. They were hands down the most recommended. And it’s safe to say, they did not disappoint. Stefano was our guide and he was incredible. In all the tours and tour companies we’ve booked in Italy (all private and reputable), this was the hands down the best and most top tier. Stefano was early to pick us up at our hotel in Florence to start our day at 830am. From morning to night, he was the most energetic, knowledgeable and fun guide we could’ve asked for. We went to San Gimingnano, Siena and a vineyard for lunch. We also asked him to drop us off at the very end at a famous leather shop in Florence (in lieu of our hotel) and he made every effort to make it prior to the close. Stefano went above and beyond to make sure Tuscany was the absolute highlight of our Italy trip. Thank you Stefano, and I hope to meet you again!
Highly recommend this tour as well as our tour guide, Stefano! The day was amazing from start to finish. Stefano made the day even better with all of his knowledge of the region and amazing stories about the history of the area. The stroll around San Gimignano and Siena was so beautiful and fun. The lunch and wine tasting at the organic locally owned winery was amazing. The food, wine and view were 5 stars! This tour is worth every dollar plus more! Definitely book it and if you can, I recommend asking for our tour guide, Stefano!
The guide meets you at the main railway station , close to the taxi rank, and McDonalds is on the opposite side of the rad, and a small kiosk selling refreshments etc, very close to meeting point. From the meeting point there is a 10 min walk to where the coach is parked. The day started at 0800 hrs, and finished at 2100hrs. The sites visited were very interesting, lunch was excellent at the winery, with excellent toilet facilities, and a shop that sells their wines. etc. The high light was the "Church/Cathedral) at Sienna is stunning and beautiful.. We were so pleased we booked the tour as we saw so much more and understood so much more than trying to do it alone. Stefano the guide was excellent, so knowledgeable, helpful and patient and funny. Thank you
Our guide Stefano and driver Luca made us feel like family. We spent the day laughing and learning and eating and drinking and exploring. It was the most perfect day. Seeing San Gimignano and Siena with them - and with a local guide and friend Alicia - brought Tuscany to life.
A wonderful tour- both our driver and guide were knowledgeable, friendly and flexible. They couldn’t have done more to make it an exceptional day- both for having fun and learning about these lovely historical places. There was the right balance of showing us around sharing the history and stories and free time to explore and shop. The view at lunch at the winery was incredible and the food and wine complemented perfectly. I wouldn’t hesitate to recommend this more personalised version as it was easy to be curious, relax and enjoy - an absolutely amazing day!
Stefano was a great driver, tour guide. We were given plenty of free time to wander around at each village. Despite the rain and cold temperatures, or trip was fun. Lunch at an organic wine farm was delicious.
We had a wonderful day ! Beautiful countryside and excellent lunch, the wine was amazing- would highly recommend this experience!
This was an amazing tour. Stephano was our driver/guide. He was very personable and definitely made the trip one to remember It rained most of the day but we were able to make the best of it. San gimignano was amazing and wish there was a little more time there. The winery was limited due to weather but the staff did a great job and we still had a great experience. Plenty of wine. Siena was great and our guide was very informative and accommodating for a member of our group that wasn’t a little slow moving that day. I can’t recall her name, I apologize. I highly recommend this tour.
Loved having lunch at the Tuscan farm/winery. Food, wine and views were unforgettable!! Our guides, Sara and Francesca made the day a perfect one! It was so nice to have a small group tour to escape the crowds.
Everything was great,just perfect,Sara and Francesca are great, professional and very very nice.I like this tour very much and I recommend.
Started the tour very smoothly with Sara and Francessca - amazing tour guides! We were a small group of 4. First was San Gimignano - we had a few hours there, lovely little town! Sara gave us great tips to go up La Rocca to have amazing views of the Tuscany wineries and also had the recommended gelato which was extremely smooth. We had a lunch at a local winery - the pasta and wines were delicious! Followed by an antipasti plate. Personally would’ve liked a bit more food, but there was plenty of wine! And an amazing view of the winery and San Gimignano. The last stop was Siena, lovely little city - had an awesome local guide and viewed the duomo! Overall recommend this tour! Thanks Sara and Francessca for the great day!
Great lunch and tasting with gorgeous views! Our tour guide, Emma, was super! Thanks for making for a wonderful Tuscany experience!
If I could give 10 stars I would! The guide Stefano was absolutely amazing as a tour guide!!! so informative and it was easy to ask him questions. He went above and beyond to tell you the background and history behind what you’re seeing and it was so so fun! The countryside is breathtaking. San Gimignano is charming and has great shops. The lunch and the winery is fantastic. Beautiful view from where you sit! Sienna has a very interesting history that you will love hearing about. Another guide Beni gave us additional information the was fascinating.
Stefano was our driver and guide. He is the best from his knowledge and personality to his driving skills. We felt like a family member was guiding us through the day. Tour was so well organized and coordinated. The lunch was delicious at the winery/organic farm. We had time at both locations to explore and shop. Both locations are charming and worth a visit but both are packed with tourists. I highly recommend this tour.
Fantastic tour with a wealth of information that only a local can provide. Best tour guide ever, who provided an impressionable experience!
We had a group from New York State that took this tour with Gabriel (named for an Argentinian futbol player). He was very personable and made the tour fun by adding his own experiences and stories. I learned so much, as this is my first time in Italy, and would definitely take a tour with him again. He was very conscious about making sure that everyone was accounted for. I totally recommend him and Walkabout Tours.
We had a wonderful time on this tour! Our tour guide, Stefano, was very knowledgeable and super kind. He ensured the tour stayed on schedule and showed us the most beautiful locations. He answered all of our questions and really made the tour worthwhile. The cities were interesting and the winery was beautiful. We're happy we chose the tour that stops in 2 cities instead of the option that stops in 3 cities, as we were tired by the end of the tour. Well worth the money for the experience.
Spectacular tour, very well organized, recommended stra. Special thanks to the guide Alessandro, the driver of the bus Giancarlo and in general to the agency. Top!!! Thank you!!!
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