Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery
Recommended by 97% of travelers
Florence, Italy
- 12 hours (approx.)
- Mobile ticket
- Offered in: English
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Overview
Venture into Tuscany on this day trip from Florence and discover the region's highlights with the help of a local guide. Explore the medieval city of Siena and its cathedral before heading to the hills of Chianti for a Tuscan lunch and wine tasting (optional). Roam the streets of San Gimignano and travel to Pisa to admire the architectural drama of Cathedral Square—home to the UNESCO-listed Leaning Tower of Pisa. Upgrade to include admission to climb the tower.
- See a side of the Tuscan countryside you'd easily miss without a guide
- Take a guided tour through Siena, with entry to the gothic Cathedral
- Set your own pace to explore Siena, San Gimignano and Pisa
- Upgrade to include a hearty lunch and wine tasting in Chianti
Why Travelers Choose This Tour
This day trip includes lunch at an organic family-run wine estate with Chianti views.
Sample Menu
Starter
Fettunta with extra virgin olive oil, served with local Vernaccia white wine
Main
Pasta with traditional Chianina beef ragù, paired with Chianti Classico wine
Main
Homemade cured meats, local cheeses, garden-fresh salad, ChiantiClassico Riserva
Dessert
Tuscan biscotti, served with a glass of local Vin Santo dessert wine
What's Included
- Air-conditioned vehicle
- Professional English speaking tour guide with you for the whole day
- Guided walking tour of Siena with entrance fee to the cathedral
- Hearty farmhouse lunch – veggie and gluten-free options available
- Wine tasting of four varieties
- Free time to explore the towns at your own pace
- Gratuities
- Hotel pickup and drop-off
- Food and drinks, unless specified
Meeting and Pickup
Meeting point
- Piazza della Stazione, 27, 50123 Firenze FI, Italy
Check-in: 7.45am - Your guide will be holding a WALKABOUT TOURS sign, right by the taxi stand at Santa Maria Novella train station across from the outside McDonald's
End point
This activity ends back at the meeting point.Itinerary
Board your coach in Florence, and travel into the hills of Tuscany where the city of Siena awaits. Join a guided tour of the city with a visit to Siena Cathedral and Piazza del Campo. Then, make the most of some free time to set your own pace, and perhaps enjoy a coffee in the sun alongside the locals.
From Siena, return to the Tuscan countryside to explore the Chianti wine region. Stretch your legs with a stroll through a vineyard, olive grove and wine cellar, and refuel with a Tuscan winery lunch and wine tasting (upgrade).
After lunch, journey onward to San Gimignano with its medieval towers, cobbled streets and squares. Here, your guide helps you find top attractions on a map so that you can explore the town independently. You have about 1.5 hours free time to wander amid the town and its 14 towers
Travel from San Gimignano to Pisa: your final stop of the day. Follow your guide to Cathedral Square to discover Pisa Duomo, Pisa Baptistry, the monumental cemetery (aka Camposanto) and, of course, the Leaning Tower of Pisa. If you’ve booked an upgraded tour, you can climb the tower.
Return to Florence in the early evening, and finish your Tuscany tour with a drop-off at the start point.
From Siena, return to the Tuscan countryside to explore the Chianti wine region. Stretch your legs with a stroll through a vineyard, olive grove and wine cellar, and refuel with a Tuscan winery lunch and wine tasting (upgrade).
After lunch, journey onward to San Gimignano with its medieval towers, cobbled streets and squares. Here, your guide helps you find top attractions on a map so that you can explore the town independently. You have about 1.5 hours free time to wander amid the town and its 14 towers
Travel from San Gimignano to Pisa: your final stop of the day. Follow your guide to Cathedral Square to discover Pisa Duomo, Pisa Baptistry, the monumental cemetery (aka Camposanto) and, of course, the Leaning Tower of Pisa. If you’ve booked an upgraded tour, you can climb the tower.
Return to Florence in the early evening, and finish your Tuscany tour with a drop-off at the start point.
Additional Info
- Confirmation will be received at time of booking
- Not wheelchair accessible
- Stroller accessible
- Near public transportation
- Infants must sit on laps
- Travelers should have a moderate physical fitness level
- Due to uneven surfaces, we cannot accept anyone with walking difficulties or using a wheelchair
- Vegetarian option is available, but we regret that gluten free or other alternative dietary requirements cannot be catered for
- It is recommended to book any rail travel from Florence after 9pm to allow time for any traffic delays on your return journey
- When the Duomo of Siena is closed for religious services, Palazzo delle Papesse will be visited instead
- Operates in all weather conditions, please dress appropriately
- Please note: For the Leaning Tower of Pisa children under the age of 8 are not admitted. Children between 8 and 12 years old must be accompanied by an adult and held by the hand at all times while you are in the Leaning Tower of Pisa. Teenagers between 13 and 18 years old must be accompanied by an adult while you are in the Leaning Tower of Pisa
- Full Tour option includes the visit to Pisa but not the ticket to climb the Leaning Tower
- Full Tour plus Leaning Tower Tickets option also include the tickets to climb on the Leaning Tower in Pisa.
- This tour/activity will have a maximum of 40 travelers
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Cancellation Policy
You can cancel up to 24 hours in advance of the experience for a full refund.
Traveler Photos





Featured review
Marlene_M
⭐⭐⭐⭐⭐
What an absolutely outstanding day in Tuscany!
From start to finish, this tour exceeded expectations. Our guide, Néomi, was phenomenal — knowledgeable, warm, organized, and perfectly paced. She delivered rich history, cultural insight, and thoughtful commentary without ever overwhelming the group. Her guidance in Siena especially elevated the experience — it was my absolute favorite stop of the day.
And Giuseppe — what a professional. Smooth, confident driving through Florence to the Tuscan countryside, perfectly timed arrivals, and an overall calm presence that made the entire journey feel seamless and safe. We were even instructed to keep our original seats on the bus, which eliminated confusion and kept everything running efficiently. Small detail, big impact.
The winery lunch? Beyond expectations. This was not a “tasting.” Three full bottles of excellent wine shared among four people, paired with a beautifully prepared, abundant Tuscan meal. Generous, authentic, and absolutely delicious.
Yes — there is a fair amount of walking (especially in Siena), but every step was worth it. The scenery, the charm, the architecture — unforgettable.
This tour was perfectly guided, exceptionally organized, and delivered a true taste of Tuscany in one day.
Highly recommend — and if you can, hope you get Néomi and Giuseppe!
Reviews
4.9
based on 21,851 reviews
Thomass_M, Mar 2026
Best Tour experience of our Italian trip, Mano was absolutely fantastic tour guide. Knowledgeable, professional, and friendly. Our this tour on you must do list.
Celeste_V, Mar 2026
We absolutely loved this tour! Manolo was a fantastic guide and it was impressive how well Sergio navigated the narrow winding roads with the tour bus.
Siena and San Gimagnano were beautiful gems that we would have missed had we not done this tour. The lunch at the winery was filling and delicious and the views were incredible.
We couldn’t have asked for a better day and we’re grateful to Manolo and the Walkabout Tours staff for all of their efforts to make it special. We would highly recommend this tour.
Camille_Y, Mar 2026
Manolo and Emilio made the experience effortlessly fun. Felt like we were in great hands for our trip. Would definitely recommend. Especially for a day free of stress/planning, it was great to just be along for the ride with knowledgeable, friendly hosts
William_G, Mar 2026
It's a lot of walking up and down hills but well worth it for the views . The rides through the countryside and lunch at the winery were wonderful
Joan_L, Mar 2026
We had a fantastic day with Mano yesterday! He was extremely informative and an outstanding guide who always kept us on track for time so that we could enjoy the full experience! Our driver (whose name I can’t remember but it started with an M) was a great driver, very friendly, and we appreciate his excellent driving!
Response from Host, Mar 2026
Thanks so much for the lovely review! We're really happy to hear you had such a great time. Our goal is to make it easy, fun, and memorable — so it means a lot to know you enjoyed the experience. We’d love to have you join us again whenever you’re back in the area. Safe travels and thanks again for choosing Walkabout Tours!
Christopher_P, Mar 2026
Incredible experience well worth the time
Naomi was kind, knowledgable and professional. Planning on coming back
Response from Host, Mar 2026
Thanks so much for the lovely review! We're really happy to hear you had such a great time. Our goal is to make it easy, fun, and memorable — so it means a lot to know you enjoyed the experience. We’d love to have you join us again whenever you’re back in the area. Safe travels and thanks again for choosing Walkabout Tours!
Graciela_R, Mar 2026
This was my favorite tour! Gian Carlo was a great tour guide and made sure that everyone was enjoying the trip and attentive to everyone’s needs.
Response from Host, Mar 2026
Thanks so much for the lovely review! We're really happy to hear you had such a great time. Our goal is to make it easy, fun, and memorable — so it means a lot to know you enjoyed the experience. We’d love to have you join us again whenever you’re back in the area. Safe travels and thanks again for choosing Walkabout Tours!
Hadeel_J, Mar 2026
Our Tuscany tour was truly unforgettable—absolutely stunning and worth every penny. From Sienna to Bisa, and vineyards to the charming historic towns, every moment felt like something out of a postcard.
What made the experience even more special was our tour guide. He was incredibly knowledgeable, and attentive, bringing each destination to life with fascinating stories and insights. You could tell he genuinely cared about making sure everyone had an amazing time.
Response from Host, Mar 2026
Thanks so much for the lovely review! We're really happy to hear you had such a great time. Our goal is to make it easy, fun, and memorable — so it means a lot to know you enjoyed the experience. We’d love to have you join us again whenever you’re back in the area. Safe travels and thanks again for choosing Walkabout Tours!
Jordan_W, Mar 2026
Giancarlo was the absolute best!!! Our new Italian cousin. You could tell he was knowledgeable about the history and made a very long day, very fun!!
Response from Host, Mar 2026
Thanks so much for the lovely review! We're really happy to hear you had such a great time. Our goal is to make it easy, fun, and memorable — so it means a lot to know you enjoyed the experience. We’d love to have you join us again whenever you’re back in the area. Safe travels and thanks again for choosing Walkabout Tours!
Andre_B, Mar 2026
First of all, our guide Mano deserves a 5 star rating. There are some issues with the tour though. The tour tries to pack in too much to get a good visit at all the sites. The stop at Gimignano should be dropped alltogether to allow for more time at other sites. Gimignano is worth visiting if scheduled properly. The promo picture shows tourists walking around a vineyard, suggesting some description of the site by the owner or our guide, and there was no such thing. The meal was OK, so were the wines and oils. This stop at the vineyard felt more like a sales pitch for the winery. The stop over in Pisa left enough time to explore the leaning tower but not enough to visit the cathedral properly.
Nancy_K, Mar 2026
Giancarlo was the best guide! He was extremely knowledgeable and made the day so much fun. The day was long so be prepared to walk!
Response from Host, Mar 2026
Thanks so much for the lovely review! We're really happy to hear you had such a great time. Our goal is to make it easy, fun, and memorable — so it means a lot to know you enjoyed the experience. We’d love to have you join us again whenever you’re back in the area. Safe travels and thanks again for choosing Walkabout Tours!
Rosemary_G, Mar 2026
Wonderful day. Alessandro was amazing and so informative. A great day touring beautiful scenery and great food!
Response from Host, Mar 2026
Thanks so much for the lovely review! We're really happy to hear you had such a great time. Our goal is to make it easy, fun, and memorable — so it means a lot to know you enjoyed the experience. We’d love to have you join us again whenever you’re back in the area. Safe travels and thanks again for choosing Walkabout Tours!
Jennifer_R, Mar 2026
The day was fabulous and worth every penny! Our bus driver did a great job keeping us safe and comfortable while our guide Alessandro kept us well informed and on pace throughout the day. He was kind and helpful, and gave great recommendations. The shops and views at Siena- wow! The lunch and views at San Gimignano- surreal! The Leaning tower of Pisa at sunset- unreal! The day is fast paced and, yes, you will be walking a lot, but you won’t be disappointed nor feel like it’s tedious. A must do!
Response from Host, Mar 2026
Thanks so much for the lovely review! We're really happy to hear you had such a great time. Our goal is to make it easy, fun, and memorable — so it means a lot to know you enjoyed the experience. We ’d love to have you join us again whenever you’re back in the area. Safe travels and thanks again for choosing Walkabout Tours!
Stephen_B, Mar 2026
Family loved the tour. Jin Carlo was awesome. Directions to the meeting place were not ideal but overall excellent tour and would highly recommend.
Bhaskar_K, Mar 2026
We had a fantastic day trip to Tuscany! Our guide, Mano, was excellent and shared so much interesting history about Siena, San Gimignano, and Pisa. The food and drinks were a highlight, too. Highly recommended!
Response from Host, Mar 2026
Thanks so much for the lovely review! We're really happy to hear you had such a great time. Our goal is to make it easy, fun, and memorable — so it means a lot to know you enjoyed the experience. We’d love to have you join us again whenever you’re back in the area. Safe travels and thanks again for choosing Walkabout Tours!
Sally_L, Mar 2026
It’s a long day but so worth it . Our host from Walking Tours Adela was very knowledgeable, friendly, funny and passionate about her adopted country.
Elizabeth_L, Mar 2026
It’s a long day but you get to see and experience a lot. Lunch and wine tasting was delicious. Everything was beautiful!
Rosemarie_A, Mar 2026
Exceptional tour guide in Manolo.
He was very informed and paid attention to all your needs. I would highly recommend him, and would definitely ask for him for any future tours.
Lev_K, Mar 2026
It was an unforgettable tour—three historic towns in one day!
Lunch at the winery was excellent, with plenty of delicious food and wine.
Our tour guide, Miri, was very knowledgeable, friendly, and always ready to answer any questions about Italian history.
Eric_U, Mar 2026
At first I was worried that the day would feel too long, but it was actually perfect! I'm convinced we had the best guide, Mano!! Mano was the best. He was really funny too. Very knowledgeable about all the places we went. He was very kind. He answered all the questions we had and even gave us some good food recommendations in Florence.
We bought souvenirs in just about every place we went and we were able to keep our stuff on the bus in between stops. Did we walk a lot, yes. Was it too much walking for us, no. That was the best way to see the details of the towns. The walking pace of the tour guide in Siena was perfect. I appreciated having free time in every place that we visited. We LOVED Siena, we debated going back the next day haha The lunch we had at the farm was 10/10. We were very impressed. It started with some bread (olive oil & balsamic vinegar), then pasta, then thinly sliced pork & roasted potatoes, and finished off with dessert. I don't remember the names of everything, but it was good (and I'm a very picky eater). There was wine that was paired with everything. It was great. They also accommodate you if you have dietary restrictions or allergies. We ended up buying 2 bottles of wine, olive oil, and balsamic vinegar from the farm. Our bus driver, Emilio was a great driver.
If you're thinking about doing this tour, do it. A word of caution if you have trouble walking or climbing stairs. I would not recommend for small kids under 5. We had 2 kids on our tour, probably around 10-12 and a young teenager, they did fine. In total we had maybe 30ish people on our bus. This tour gave us a break for the busy city of Rome which we had already explored before coming to Florence.
We went mid March, it was a bit chilly and windy (they said it was unusual). It still beat doing all that walking in the middle of summer.
Book the tour. You won't regret it.
Response from Host, Mar 2026
Thanks so much for the lovely review! We're really happy to hear you had such a great time. Our goal is to make it easy, fun, and memorable — so it means a lot to know you enjoyed the experience. We’d love to have you join us again whenever you’re back in the area. Safe travels and thanks again for choosing Walkabout Tours!
Matthew_H, Mar 2026
David does a wonderful job keeping everyone on time and giving the full Tuscany experience. He is funny and remembers everyone.
Maria_M, Mar 2026
What an AMAZING experience!! What an absolutely fabulous guide! Manolo was an absolute gem! He was funny, thoughtful & knowledgeable. He anticipated all our needs, for everyone in the group, & efficiently took care of everything. Our day went by so smoothly, moving from one place to the next with absolute efficiency. All locations were memorable & fun. Our lunch was delicious with unforgettable views. I would 100% recommend this experience when visiting Italy. Unforgettable & fun! Thank you so Manolo! You were fantastic !!!
Response from Host, Mar 2026
Thanks so much for the lovely review! We're really happy to hear you had such a great time. Our goal is to make it easy, fun, and memorable — so it means a lot to know you enjoyed the experience. We’d love to have you join us again whenever you’re back in the area. Safe travels and thanks again for choosing Walkabout Tours!
Bob_F, Mar 2026
Mano was magnificent.... He was charming, attentive, and funny.... And he made sure to keep us on schedule...
Jacob_K, Mar 2026
Great day with a true Tuscany experience. Lunch was amazing! Great storytelling from our guide Mano!
Diane_S, Mar 2026
The lunch at the Tuscan farm was amazing! Seeing Siena, San Gimignano and Pisa just added to the trip! Our guide was wonderful!
Paul_C, Mar 2026
O M G! If you come to Florence, you have to go on this tour. Not only did we get to see amazing sights but the tour guide Adell was funny, knowledgeable, and made our trip 10 times better with her great personality. Food and drinks were great and you will be blown away by the sight seeing.
Wendy_C, Mar 2026
Mano was an amazing tour guide. With great humor and kindness he made sure our entire day ran smoothly and all of us had every need met. Labi our bus driver was flawless on a very long drive.
Yimmy_R, Mar 2026
Giancarlo was an awesome guide. We learned about music, history, food and he was very enthusiastic and knowledgeable. We really had a very lovely day.
Susan_R, Mar 2026
Much time traveling in bus. Great planned stops. Too much crammed in one day/ recommend staying longer in first stops and eliminate Pisa on this tour.
Sandra_H, Mar 2026
Able to tour four places in one day. Enjoyed the lunch at the winery. Great views and food!! Tour guide was fun and knowledgeable
Response from Host, Mar 2026
Thanks so much for the lovely review! We're really happy to hear you had such a great time. Our goal is to make it easy, fun, and memorable — so it means a lot to know you enjoyed the experience.
We’d love to have you join us again whenever you’re back in the area. Safe travels and thanks again for choosing Walkabout Tours!
From $111.48
per personup to 24 hours before the experience starts (local time)
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Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery
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