from
$161
Pisa, Siena, and San Gimignano Day Trip from Florence with Tuscan Lunch
Tour Siena Cathedral, see the Leaning Tower, dine at a Chianti vineyard, and explore San Gimignano
What's included
See Tuscany's best in one day
Expert English-speaking guide
Round-trip coach transportation from Florence
Guided tour of Siena
Entry to Duomo di Siena
Tuscan winery lunch
Wine tasting with Chianti, Vernaccia, and Vin Santo
Free time in San Gimignano
Free time in Pisa
Leaning Tower of Pisa entry tickets
Guide tips
Itinerary
Meet your guide at Santa Maria Novella train station
Your day begins outside Florence's main train station, where your guide will be waiting with a sign. Board an air-conditioned coach and settle in as the cityscape gives way to cypress-lined roads and vineyard-covered hills.
Explore Siena with a guided walking tour
First, you'll arrive in Siena, a medieval city built on three hills in southern Tuscany. Follow your guide through narrow brick lanes to the shell-shaped Piazza del Campo, then step inside the Duomo di Siena—a Gothic cathedral wrapped in green and white marble stripes.
Enjoy free time in Siena
After your guided tour wraps up, you'll have time to explore on your own. Grab an espresso at a café in the piazza, browse artisan shops tucked into ancient buildings, or simply wander the winding streets before lunch.
Savor lunch and wine tasting at a Chianti vineyard
Next, your coach rolls through Chianti's vine-striped hills to a family-run organic winery. Sit down to a Tuscan feast of homemade pasta, prosciutto, aged cheeses, and cantucci cookies, all paired with estate wines like Chianti Classico and sweet Vin Santo.
Wander through San Gimignano
From the winery, you'll head to San Gimignano, a hilltop town famous for its 14 surviving medieval towers that once served as status symbols for rival families. Stroll cobbled streets lined with workshops selling leather goods and ceramics, then climb one of the towers for views over Tuscany's patchwork countryside.
See the Leaning Tower of Pisa
Your final stop brings you to Pisa, a coastal city known worldwide for one tilting marble tower. Walk across the green lawn of Piazza dei Miracoli to see the Leaning Tower, Cathedral, and Baptistery up close, then explore the historic center at your own pace before departure.
Your tour finishes in Florence
As evening approaches, you'll board your coach for the return trip to Florence. By the time you arrive back at Santa Maria Novella station, you've tasted Chianti wine, touched medieval stone, and crossed Tuscany from hill town to coast—all in one full day.
For Reference Only. Itineraries are subject to change
Select participants and date
Start times are in the product’s local time
Free cancellation up to 24 hours in advance!
Mon, 21 Sep 2026
Meeting and drop-off point
Important Details
Discover what to expect, what’s included, and everything you need to know before booking.
Good to know:
Accessibility: Unfortunately, due to the uneven and steep surfaces, this day trip to Tuscany is not suitable for wheelchair users or those who may have trouble walking.
Dress Code: Knees and shoulders should be covered for entry into the Siena Duomo and Pisa Cathedral, as is required at most religious sites.
Dietary Restrictions: Vegetarian and gluten-free options are available, but please contact us in advance so we can work with our partners to accommodate your needs.
Alcohol Consumption: This experience includes sampling 4 wines; participants must be 18 or older to drink alcohol in Italy.
Tour Changes: At times the Duomo in Siena will be closed for religious services, in which case you will visit the Santa Maria della Scala Museum instead. The itinerary of this tour is subject to change based on weather, and traffic.
Check-in: Arrive 15 minutes early for check-in at the meeting point so the group can enter sites on time.
Your 12-hour tour includes:
Expert English-speaking guide
Roundtrip transportation via air-conditioned coach from Florence
Guided walking tour of Siena with cathedral entrance
Tuscan lunch at a family-run vineyard
Sample 4 different wines
Free time in San Gimignano and Pisa
What to bring:
Comfortable walking shoes
Government-issued ID
Camera
Water
Scarf/shawl to cover knees and shoulders for religious sites
See what people are saying
4.87
182 Ratings
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Wonderful day
Thomas N.
September 11, 2026
Alessandro was incredible. We covered a lot of things, but he had a lot of energy and did a great job. Lunch was fantastic, and the wine and the winery were wonderful.
Great Tour
Pedro B.
September 06, 2026
Alessandro showed his knowledge and experience very genuinely.
Excellent tour
Scott G.
September 01, 2026
We had a great time. Angie the tour guide was very informative about each city. Maps were helpful. Lunch at the winery was delicious. My wife loved shopping in San Gimignano. The Siena plaza was quite spectacular and the video on the annual horse race provided added perspective. Would highly recommend!
Amazing tour of Tuscany
Demi R.
August 23, 2026
Manolo and Alessio were the best tour guides! My mom and I booked the day trip from Florence and loved every second of it. Siena and San Gimignano are definitely must sees if you’re in Toscana. Having Manolo made the trip a breeze, was super communicative with meeting point and departure times. He provided information and history between stops and gave us ample time to explore each place. My mom is in her 70s and both Manolo and Alessio were super patient and helpful with her getting on and off the bus. Would highly recommend taking this tour with Manolo if you can!
An Unforgettable Tuscany Experience with Mirella and Team
Alvaro R.
July 25, 2026
This was one of the highlights of our trip to Italy, and a huge part of that was our guide, Mirella. From the moment we left Florence, she made the day engaging, informative, and genuinely fun. Her passion for Tuscany, its history, culture, and traditions was contagious, and it was especially special hearing her speak about Pisa, where she lives, with such pride and affection. She shared fascinating stories throughout the drive that gave us so much context for everything we were seeing, turning the bus ride into part of the experience rather than just transportation. The itinerary was fantastic. Pisa, San Gimignano, Siena, and the winery each offered something unique, but what made the day memorable was the way Mirella connected it all together. She was incredibly knowledgeable, organized, and attentive, making sure everyone felt included and knew exactly what to expect at each stop. Despite covering so much in one day, the tour never felt rushed. A special shout out as well to Giuseppe, our excellent driver, who navigated the winding Tuscan roads with ease and kept us comfortable and safe throughout the day. And to Benedetta, our guide in Siena, who brought the city’s history and beauty to life with her own passion and insight. Mirella also had a wonderful personality, warm, approachable, and full of energy. You could tell she genuinely enjoys what she does and wants every guest to have an unforgettable experience. If you’re considering this Tuscany in a Day tour, do it. And if you’re lucky enough to have Mirella as your guide, you’re in for an amazing day. She truly made our visit to Tuscany one we’ll remember for years to come. Thank you, Mirella!
John K.
July 21, 2026
All of the tours were excellent, especially Siena! Manolo and Marta were wonderful!
Great tour and great experience. Manila was wonderful, funny and had a great knowledge.
Emanuel M.
July 18, 2026
Amazing Service and Scenery
Colin D.
July 18, 2026
Our guide, Leah, expertly got us from location to location. She provided just the right amount of history and direction to let us know what to do while exploring on our own. The winery lunch was divine and we recommend ordering some for home. The bus also was first rate. One note, the walk from the meet up to the bus was a pretty long one. That's the only unexpected thing. A wonderful day in the care of a great group.
**An Incredible Day Exploring Tuscany’s Highlights
Lee V.
July 17, 2026
This was one of the highlights of our trip to Italy. It’s a long day, but it’s packed with incredible experiences and is an excellent way to see so much of Tuscany without worrying about any of the logistics. Our guide, Manolo, was outstanding. He was knowledgeable, friendly, funny, and kept the day running smoothly while sharing interesting history and local stories throughout the day. Siena was one of our favorite stops. It’s an incredibly beautiful and remarkably well-preserved medieval city that feels much more relaxed than Florence, Rome, or Venice. We also had an excellent local guide who taught us about the Palio and the traditions of the city’s contrade. It was especially exciting because her own contrada had just won the July Palio for the first time in over 20 years, and you could really feel her pride and passion as she brought Siena’s history to life. San Gimignano was another highlight. Seeing its famous towers from across the valley, it’s easy to understand why it’s often compared to a medieval Manhattan skyline. The town itself is small, beautifully preserved, and a wonderful place to wander the narrow streets, browse the shops, and simply soak in the atmosphere. The lunch at the Chianti winery exceeded our expectations. The setting was beautiful, the homemade food was delicious, and the wine was incredibly generous. Rather than just a few small tasting pours, bottles were brought to each table to enjoy throughout lunch, making it feel like a true Tuscan meal. At the start of the tour, the staff also asked everyone on the coach about dietary requirements. My wife is vegan, and they prepared a fantastic vegan meal for her without any hassle, which was a thoughtful touch. Climbing the Leaning Tower in Pisa was a unique experience and a perfect way to finish the day. We travelled well over 300 km throughout the day, but the comfortable, air-conditioned coach actually became one of the unexpected highlights. It was very hot during our visit, so each drive between destinations gave everyone a chance to cool off, relax, and recharge before exploring the next destination. We were travelling as a family with four boys, and everyone had a great time. Despite being a 12-hour tour, it never felt rushed, and there was a great balance of guided experiences and free time. If you’re looking for the best way to experience the highlights of Tuscany in a single day, we can’t recommend this tour enough. And if you’re lucky enough to have Manolo as your guide, you’re in for an unforgettable day.
Blast in Tuscany
Yasmin T.
July 11, 2026
Mano and Giuseppe we exceptional. Mano was amazing at explaining everything making us feel comfortable immediately! I hope to get another tour with him as the guide soon!
Fantastic Experience!
Katherine M.
July 07, 2026
All four of us absolutely loved Giancarlo and the tour. We learned a lot from the very entertaining Giancarlo, and saw absolutely amazing places. The coach was comfortable, the food at the winery was delicious, Giancarlo was clear, helpful, and kept us safe and the entire day was definitely one of our favorite experiences of the summer. We all highly recommend this experience!
Tuscany in a hot day
Andrew H.
June 21, 2026
The tour was great; everything it promised. Although it was a hot day Alex and the team had a great itinerary mixing tours, talks with rest on the bus. Glimpses of each spot with enough, not too much commentary. Lunch at Fattoria Poggio Alloro, under umbrellas, drinking their wine and the magnificent view, was the highlight of
Andrea H.
June 20, 2026
Great day!! Local tour guide Mano with Walkabout Florence was terrific!! Very well organized and knowledgeable.
Fabulous Day!
LISA F.
June 15, 2026
Highly recommend this tour! We had a fabulous day visiting Pisa, Siena, and San Gimignano. The Tuscan lunch and wine tasting were absolutely amazing, everything you could hope for and more. A special thank you to our phenomenal tour guide, Noemi, who made the day fun, informative, and seamless. One of the highlights of our trip to Italy!
Mano was amazing
john R.
June 14, 2026
Great cities, great lunch spot with more food than anyone could finish! Lovely winery. The tours were fantastic lots of great information. Mano was the best, perfect combination of information and humor. Everyone in our group loved the tour.
Recommend
Christine S.
June 01, 2026
Best trip ever with John Luca. He was so knowledgeable and the lunch was amazing!
GREAT TOUR
monica V.
May 22, 2026
Jean Luca was AMAZING, super informative and explained everything, lunch was great, thanks for the Wonderful tour
David K.
May 08, 2026
Leah V.
May 04, 2026
Alessandro and Ali were great guides! It was a great trip to see the country of Tuscany
Long and exhilarating day
Lisha P.
May 02, 2026
The tour was amazing! We saw so much in just one day and I was amazed that I could keep up so easily. Miriella, our beautiful tour guide, was extremely knowledgeable, fun and basically made the tour more awesome than I could have ever dreamed.
Amazing day seeing Tuscany
DEVON P.
April 15, 2026
My family and I throughly enjoyed this trip, Adele was such a lovely guide and provided so Much insight along the tour, we had time to explore each place on our own and take in the beautiful countryside of Tuscany! Thank you
Nicole B.
April 09, 2026
Tuscany through Montana eyes
Kathie R.
March 29, 2026
David was a conscience and knowledgeable guide. He kept us on task with humor. The guide at Sienna was local and knowledgeable also. The bus was comfortable and clean (and new).
lori H.
March 27, 2026
Robby was great! We had a great tour w him and appreciated his knowledge. The Amalfi coast is breathtaking.
Great time
Mark S.
March 27, 2026
Myrie was a great guide and would love a trip with her again and again.