Leaving Florence behind, the journey begins with a scenic drive through the rolling Tuscan countryside until the skyline of Siena appears, a perfectly preserved medieval city perched atop three hills. Known for its warm-toned brick buildings and Gothic character, Siena offers an immediate sense of stepping back in time.
Upon arrival, a short walk leads to Piazza Salimbeni, a refined and quieter square framed by elegant palaces. At its center stands a statue of Sallustio Bandini, surrounded by the historic headquarters of one of the oldest banks in the world, giving the square a distinctly noble and intellectual atmosphere.
As the tour continues, you’ll be introduced to the unique concept of the “contrade,” Siena’s historic districts. Each contrada has its own emblem, traditions, and fierce identity, all of which come to life during the famous Palio horse race. Walking through these neighborhoods reveals flags, fountains, and symbols that tell stories of centuries-old rivalries and pride.
The heart of Siena reveals itself in Piazza del Campo, a vast shell-shaped square that gently slopes toward the Palazzo Pubblico. This is the stage for the Palio and one of the most unique public spaces in Europe, where locals and visitors alike gather to relax and soak in the atmosphere.
The route then leads uphill to the magnificent Duomo di Siena, a masterpiece of Italian Gothic architecture. Its striking black-and-white marble façade and richly decorated interior—featuring intricate floors, sculptures, and works by masters like Michelangelo—make it one of the most breathtaking churches in Italy.
Next, we visit an organic, family-run wine estate—one of the true highlights of the day. Here, you’ll enjoy a relaxed and informal tasting experience, sampling regional wines such as Chianti, Vernaccia, and the traditional Tuscan dessert wine, Vin Santo. This is followed by a generous lunch featuring authentic local flavors, all served with sweeping views over the surrounding countryside. It’s the perfect moment to unwind, connect with fellow travelers, and savor fresh, organic farm produce, including homemade pasta, artisanal cured meats like prosciutto and salami, local cheeses, a crisp garden salad, and classic Tuscan biscotti.
Leaving the winery, the journey continues through vineyards and olive groves to San Gimignano, often called the “Medieval Manhattan” for its skyline of ancient towers. This UNESCO-listed hill town offers a striking contrast with its vertical silhouettes rising above the countryside.
Entering the town, you’ll find yourself in Piazza della Cisterna, a triangular square named after the well at its center. Surrounded by towers and medieval houses, it’s a picturesque and lively spot, perfect for pausing and taking in the timeless ambiance.
A few steps away lies Piazza del Duomo, the town’s religious and civic center. Here, the Collegiate Church stands opposite the Palazzo Comunale, creating a harmonious space that reflects the balance of power in medieval life.
The visit continues to the Rocca di Montestaffoli, a fortress offering panoramic views over the surrounding countryside. From this vantage point, the rolling hills, vineyards, and distant villages create a quintessential Tuscan landscape.
In the afternoon, the itinerary heads west toward Pisa, a historic maritime republic known worldwide for its architectural treasures. The city’s atmosphere blends academic energy—thanks to its university—with centuries of history.
Arriving in Pisa, you’ll step into the remarkable Piazza dei Miracoli, a vast green space where some of Italy’s most celebrated monuments stand in striking harmony. This UNESCO World Heritage Site showcases an extraordinary collection of Romanesque architecture.
The visit naturally culminates at the iconic Leaning Tower, Pisa’s most famous landmark. Instantly recognizable for its distinctive tilt, this elegant white-marble bell tower has fascinated visitors for centuries. Whether admired from afar or up close, it provides the perfect opportunity for memorable photos and a fitting finale to a day rich in history, culture, and unforgettable landscapes.
You will be dropped off in Florence at around 8.30pm with a camera full of pictures, a stomach full of hearty Tuscan food and a host of new friends.
We had a wonderful time touring the Tuscan countryside with our outstanding, knowledgeable guide Mano. Definitely one of the highlights of our entire trip to Italy!
Sara was a very enthusiastic, knowledgable tour guide, she made the trip sparkle just a bit more than necessary. I enjoyed the trip more because she was the guide.
Sara and driver Gaspar were wonderful!! All of the locations are beautiful and the lunch at the winery was fantastic!
Prepare to enjoy and experience Tuscany. Remember to wear good walking shoes. Alex was fun guide and Millo was a great driver.
Absolutely stunning. Amazing trip. Alex was an incredible guide. Excellent, thorough information and very engaging with us all. Wonderfully enjoyable. Bus driver (I can't remember his name, Gusard??) was always on time, kept us safe, and has quite a sense of humor. Trip is a must if you want to get a taste of Tuscany.
Adela was a great tour guide! Super friendly, spirited, and gave helpful recommendations. This tour is a quick sampling of different areas and experiences in the Tuscany region. I booked this trip because the Leaning Tower of Pisa was on my list of things I wanted to see, and was happy to have Siena and San Gimignano as bonuses. I especially enjoyed the lunch break at the winery in the Chianti region — beautiful view and a delish meal. Although I did feel a bit rushed in each city, to be fair you are covering 4 different spots around Tuscany so it’s to be expected. Overall it’s a great day trip to take out of Florence!
This was our first tour in Tuscany and Manolo blew us away on the first few moments we arrived at the bus. He was positive, kind, and always considerate for the group and individuals that needed care. This was the best tour we've ever had! We learnt so much of the history, stories and culture on the cities we visited, before and during the visits. We recommend this tour to the highest.
Adela and Mario were hands down the best guides so far. The winery was fantastic. Really loved their whites - vellachio 2024 and their chianti classico. Adela was very knowledgeable in sharing with us fun facts, history and interfacing us with her Siena counterpart while making sure we were super comfortable. Only qualm was that group was a tad big. Then again could be on us for missing out the fact that the listing did not say small group tour. Other than that, no complaints.
This experience was well worth it! We would recommend it to anyone looking for a day full of history, stunning views and a wonderful lunch. Siena was small, but beautiful with a unique story. San Gimignano has stunning views and tasty ice cream. Pisa, of course, has the tower. The day was well planned out - our guide, Adela was outstanding. She was very friendly and very knowledgable. The transportation was timely and comfortable. Our driver did a great job getting us all safely from one location to another. We did plenty of walking so be prepared with appropriate attire!
Monolo was very good guide, caring, attentive and with sense of humor. The trip was well organized and coordinated. The only thing was that the picture shows walking through the winyards at the countryside which we didn't do much at all and the food for the wine tasting was less than basic.
Very organized, first class trip led by expert guide Alessandro. He was charming and very informative with history and local culture which really made the trip .. Great value as you got to see the highlights of 3 cities in one day. Fabulous local guide in Siena. The wine tasting and lunch was generous and delicious. My friend and I were able to climb the Leaning Tower and walk around the surrounding area in Pisa which only 3 of us dodo did but I recommend.
Just wow. Mano did a great job keeping the very large group together. His knowledge was very impressive and his personality was the icing on the cake! The sights were very impressive
This tour was well organized and timed perfectly. Our bus driver was friendly and a safe driver. The bus was clean and comfortable. Our guide, Adela, kept everyone engaged during the bus ride. She provided a lot of information about what we would see and do before each stop. She took time to answer all questions, gave very clear directions as to meeting spots and meeting times as well as recommendations on what to do during free time always lwith a smile! I loved the wine tasting and lunch. It was a wonderful way to sample food, wine, and get to know other people on the tour. I recommend doing the climb up the Tower of Pisa. The view was fantastic and there was space to step to the side if you need to take a break to catch your breath. I didn't plan to climb when I first reserved my tour, but after we arrived at Pisa, we were told that those who didn't have tickets to climb and wanted to could purchase a ticket on site, so I did. If you only have a day to visit areas outside of Florence, this tour is a great way to do it without having to worry about driving yourself and finding your way.
Our tour guide was top notch!! We Highly recommend this tour.
Alessandro and Guisepi were both fantastic we enjoyed the day very much. Both were very knowledgeable and helpful.
Great day!!! Lunch at the winery was delicious with breathtaking views. Tour guide, Adele was fantastic!
Pisa is underwhelming, try to spend little time here. Farm lunch is amazing! Great trip but Giancarlo made the trip exceptional. When you got it, you got it!
Wife and I had an amazing day trip through Tuscany. Miri was our guide extraordinaire and made our experience even better than we imagined, highly recommend!
We didn’t have much time in this region of Italy but we wanted to see what we could fit in a day and I think this tour was perfect for the time we had. I wish we did have a bit more time in each location as I felt like we were rushing to do activities in one area HOWEVER it is not the fault of the company. It’s close to the end of the year and the sun goes down earlier now so we had to go go go and try to get to the meeting point as instructed. We had Coco as our tour guide and I think she way too cute and is very enthusiastic about her city and the tour itself. We also had Alessia (sp) in Siena and it was great to have a local guide take you around. Stefano was our driver and he kept us all safe. Coco was also personable and always checked on the group to make sure we’re ok or if we had any questions. If you don’t have much time like we did, try this tour! Lunch was delicious as well (it may not be enough for big eater) and I had to bring home some alcohol— it’s so good!
Long day BUT WORTH IT! This well organized 12 hour day tour took us on an incredible journey to all the places we wanted to see and experience. Fortunately the weather cooperated, our guide was good but I got a bit weary of his opinions .
We had an amazing day thanks to David and our wonderful bus driver- they ensured that everything went smoothly. David was a funny, interesting guide too. Beware this is a full 12 hour day with lots of bus time because the towns are a long way apart- do not book if you are not happy with that but this is the only way to see such a variety of places in one day. Roberta was our guide in Sienna- very informative and interesting. The cathedral is stunning. The winery was lovely with SO much food and wine! Bottles on the table to help yourself. Then another red. Then a desert wine. Stunning views overlooking the towers of Dan Gimignano. San Gimignano is beautiful but a tourist trap. We had about an hour. Go up La Rocca for amazing views. Pisa was beautiful at sunset. The cathedral was gorgeous. Again, a tourist trap with everyone getting their perspective pictures. It really was a day worth doing and I recommend. Make sure you have your walking shoes on!!
12 hour day but somehow didn’t seem long enough. Siena was beautiful and great architecture. Tuscany was great and the winery tour food and drink were exceptional San G was amazing too
Wonderful tour and awesome guide!
Mano was the best! He was super funny and I loved having him as a guide. Very knowledgeable! I wish I could relive this day all over again. Our bus driver was absolutely incredible as well…. Kudos to him for navigating those roads!
A long day but excellent tour. Our tour guide Adella was fantastic. She knew so much about the region.
We had such a great time exploring Tuscany. The whole experience was amazing, and a big part of that was our tour guide, Miri. She was super friendly, funny, and incredibly knowledgeable. She kept the tour fun and entertaining while making sure we stayed on schedule without ever feeling rushed. We still got to see and enjoy the best parts of each destination. You could really tell she knew what she was doing and genuinely enjoyed sharing the experience with everyone. We had an unforgettable day and would definitely recommend this tour, especially with Miri as your guide!
Miri was FANTASTIC! We had a great time and the experience was excellent! We loved seeing 3 sites in a day. I appreciated that there were no store stopped where you are “forced” to buy things that are of bad quality. Miri gave us time to explore each town and shop at our own leisure. The farm visit for lunch was gorgeous and the food was yummy! The bus was comfortable and the scenery, the people and food was great. You will truly enjoy your time! Just book the trip- you won’t regret it!
Miri was amassing during the tour! She was super knowledgeable and was very passionate! We loved spending the day with her!
Miri, our guide she is amazing, very knowledgeable, friendly, have good energy and vibe! The tour it self is also amazing, we had lunch at the winery have fantastic view, and we had enough time and really enjoyed the trip !
Coco and (driver sthefano) was amazing people, super friendly, thank you to our guide coco. Gracie ty.
Wonderful way to see three Tuscan towns in one day! We especially enjoyed visiting the organic farm/wine lunch.
It was Too long. They don't prepare you for the long and dangerous walks. The wine portion the best.
I ordered wine from the winery where we had our lunch in Tuscany. We’ve been back over 2 weeks and still have not received it.
Very well organized, Coco is super cool guide, with good english, interesting information and funny jokes!
Stefano was a great driver! Kept water up in the front available to folks throughout the day. Coco was the best tour guide. Impeccable English, incredibly knowledgeable, high energy, fun positive attitude.
Excellent trip. Great tour guide Mano was awesome. Saw all the major towns and attractions in one day with lunch at a winery which was amazing.
Meri was absolutely amazing. Incredible person and very helpful. The trip was complete worth it and Tuscany is a once in a lifetime experience. Perfect amount of time to see everything and get the proper Tuscany experience
Amazing tour and we covered a lot of ground in 12 hours. More walking than I expected - about 16,000 steps - so if walking is a challenge this tour may not be for you. N
alessandro was amazing- i would choose him again-he made the trip so exciting and interesting at the same time.
The day trip to places in Tuscany was wonderful! Our tour guide, Lea, could not have been any nicer or more organized, and she went out of her way on the trip home to offer recommendations for places to visit and things to do as we continued our vacation to other parts of Italy. We thoroughly enjoyed our time in Siena and San Gimignano. Siena’s duomo is stunning and the views in San G. are breathtaking. We also enjoyed learning the history of the towns. Pisa wasn’t nearly as impressive as the other two towns, but it was fun to see the famed tower. Getting away to the Tuscan countryside is a must.
Great way to see more of Italy! Luca led the group throughout the day. He was well versed in the history of the towns that we visited. A pleasure to listen to. Lunch at the winery was delicious and enjoyable. The views were spectacular! Our last stop at Pisa was tourists dream. Beautiful buildings and a cathedral surround the leaning tower. Lots of walking. The bus rides were comfortable. Thanks to Luca for making such a great trip.
What an amazing day! Early start at the main railway station where we met our guide, Jean Luca. He was great, very knowledgeable, fun and very entertaining. It was a packed day with lots to see. I would definitely recommend this tour. Make sure you bring snacks, wear walking shoes & have fun!
Absolutely loved everything about this tour. Angela was an incredible guide. The lunch overlooking Sangi was incredible. The view, the food, the wine… incredible. Would absolutely recommend this tour if you’re staying in Florence and are wanting to check out other area’s of Tuscany.
This was a great tour! Covered 3 cities in just one day. The cathedral was spectacular and the farmhouse lunch was really good! Our guide, Angela, made the tour the best.
Gianluca 大一郎 Rossi was hands down the BEST tour guide we could have ever asked for! Our Tuscany adventure was undoubtedly one of the biggest highlights of our entire girls’ trip, and so much of that was thanks to him. We fell so deeply in love with the experience that Siena has officially become a destination we cannot wait to revisit! From the charming medieval streets of Siena and San Gimignano to the iconic Pisa and winding countryside, every part of the day was incredible. His organization and attention to detail were absolutely amazing. Everything ran seamlessly, from the effortless check-ins to coordinating our stops and making sure everyone was accounted for. He went above and beyond to ensure that every group felt accounted for, comfortable, and were having fun. And then there’s Gianluca’s personality! What an absolute gem of a human being! His positivity, energy, warmth, and genuine enthusiasm made the entire day such a joy. He’s a natural storyteller who shared fascinating historical context, cultural insights, and little-known details that truly brought each town to life. Gianluca even went out of his way to share a restaurant recommendation that our entire group absolutely fell in love with! We loved the tour and honestly couldn’t have imagined a better way to experience Tuscany. We left with incredible memories, a newfound love for Tuscany. If you’re considering this Tuscany day trip, DO IT! And if you’re lucky enough to have Gianluca as your guide, you’re in for an absolute treat. Gianluca, thank you so much! We couldn’t have asked for a more wonderful guide or experience. Grazie mille! Until next time.
It was a great day trip with Manolo the guide and Guseppe the driver. Everything was very well organised, on time and enjoyable the whole day. Manolo is very knowledgeable with great communication skills. Definitely can be recommended for a fun day out.
We had a great experience with walk about tours especially with Luca who made the tour more fun and enjoyable. Highly recommended.
Luca was a great tour guide. He sat his expectations and ensured we got back on time. He was very friendly and very informative. He gave us a lot of information about Florence, San Giamanino, Pisa and Sienna. I recommend Luca to anybody
An awesome experience. Such a good mix of time with the guides and free time to explore on your own. Our guide Luca was incredible! Very knowledgeable, enthusiastic and make our tour great.
Jean Luca was an amazing tour guide. I highly recommend this trip. Sienna & San Gimignano were the highlights.
Monday through Friday 9 am to 7 pm EST
Reach us by phone
Reach us by email