Private Siena San Gimignano Tour from Florence with Winery Lunch
Pick your date
Highlighted days have spots open. Grey days are sold out or not running.
September 2026
Loading live availability
Who is going?
Adults
Age 13 and over
Children
Age 12 and under
Select a highlighted day to see live departure times and the exact price for your group.
Free cancellation up to 24 hours before. Same price on Viator, Outty earns a commission.
Traveler rating
4.9/5
Based on 25 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Private Siena San Gimignano Tour from Florence with Winery Lunch worth booking?
Private Siena San Gimignano Tour from Florence with Winery Lunch is a 10-hour experience in Florence, Italy, from $480 per person. It scores 64 out of 100 on the Outty Ranking, which we label “Solid Choice”, based on a 4.9/5 rating across 25 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 64 / 100
- Rating
- 4.9/5 (25)
- Duration
- 10 hours
- From
- $480 per person
After leaving Florence you will travel toward San Gimignano and enjoy the views of vineyards and rolling hills as you listen to the fascinating history of this town. On arrival your guide will walk you to the main gate
What you get
About this experience
After leaving Florence you will travel toward San Gimignano and enjoy the views of vineyards and rolling hills as you listen to the fascinating history of this town. On arrival your guide will walk you to the main gate and you have free time to roam the picturesque streets and squares. Maybe browse the local shops, try an award winning gelato or walk among the town’s famous medieval towers. Next we stop at an organic, family-run wine estate. You will enjoy a traditional local lunch with plenty of wine, and soak in the idyllic location overlooking stunning views of the surrounding countryside. After lunch, view Siena through the eyes of a local as you join a guided walking tour through the medieval city. Learn about the world’s oldest bank, see the Piazza del Campo - the site of the 600-year-old Palio horse race - and admire the interior of the Duomo, a treasure chest of artworks. Afterwards, enjoy Siena at your own pace with free time for shopping or relaxing in an open-air cafe.
What travelers are saying
Outty’s summary of the themes that recur across 25 traveler reviews. Written by us, not quoted from reviewers.
The guide
9 mentionsTravelers single out the guide as the reason the experience works.
Knowledge and storytelling
7 mentionsReviewers describe the commentary as informative rather than scripted.
Food and drink
6 mentionsThe tastings and food stops are a highlight for most reviewers.
Photo opportunities
3 mentionsThe views and photo stops come up again and again.
Value for money
2 mentionsTravelers feel they got more than they paid for.
Organization
2 mentionsPickup, timing, and logistics are described as running smoothly.
Traveler reviews
25 verified traveler reviews for Private Siena San Gimignano Tour from Florence with Winery Lunch. Ratings and reviews provided by Viator and Tripadvisor.
Best part of Tuscany wasn’t the places it was the people
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.
via Tripadvisor
⭐ Fantastic Tuscany Day Trip – Siena, San Gimignano, Pisa & Wine Country
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! 🇮🇹🍷🍇📸✨
Response from the operator: 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!
via Tripadvisor
Incredible tour!!!
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!!!
Response from the operator: 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!
via Tripadvisor
So much fun and educational!!!
Luca was amazing! We learned so much history and had fun exploring Sienna, San Gimignano and Pisa! Would definitely recommend for a day trip :)
Response from the operator: 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!
via Tripadvisor
Excelente servicio de Emma y Guiseppe!!
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 !!
via Tripadvisor
Good to know
- Duration
- 10 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Booked in 30 days
- 9
- Verdict
- Solid Choice
Why this scores 64
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Private Siena San Gimignano Tour from Florence with Winery Lunch: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Florence.
How much does Private Siena San Gimignano Tour from Florence with Winery Lunch cost?
+
Prices start at $480 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Florence usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.
How long does Private Siena San Gimignano Tour from Florence with Winery Lunch take?
+
Plan for about 10 hours from start to finish, not counting travel to the meeting point. Most travelers leave another 30 minutes on either side so the rest of the day in Florence is not rushed.
Is Private Siena San Gimignano Tour from Florence with Winery Lunch worth it?
+
It holds an Outty Ranking of 64 out of 100, which we label "Solid Choice". That score blends traveler sentiment (4.9/5 across 25 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable last minute in Florence, and how flexible the cancellation terms are.
Can I cancel or reschedule Private Siena San Gimignano Tour from Florence with Winery Lunch?
+
Yes. Cancel free up to 24 hours before the start time for a full refund. Inside that window the booking is non-refundable, and no-shows are not refunded.
Is Private Siena San Gimignano Tour from Florence with Winery Lunch suitable for kids and families?
+
Yes, all ages are welcome. Families should still weigh the 10-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book Private Siena San Gimignano Tour from Florence with Winery Lunch?
+
Around 9 people booked this in the last 30 days, so popular slots go early. Two to three weeks ahead is comfortable in shoulder season, while summer weekends and holidays in Florence can sell out a month out. Same-day spots do open up when other travelers cancel, so it is worth checking if you are already in town.
What should I bring or wear?
+
Bring photo ID, your booking confirmation on your phone, a refillable water bottle and comfortable shoes. Dress for the weather in Florence and add a light layer if any part of the 10-hour experience runs outdoors or after sunset.
Where does Private Siena San Gimignano Tour from Florence with Winery Lunch start and how do I get there?
+
The exact meeting point and directions are on your voucher once you book, and they sit in central Florence within reach of public transport. Arrive 15 minutes early: late arrivals are treated as no-shows by most operators.
What are the best things to do in Florence?
+
On Outty we rank every Florence experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include The Best tour in Florence: Renaissance & Medici Tales - guided by a STORYTELLER, Florence Pizza or Pasta Class & Gelato Making at a Tuscan Farm, Small group Tuscan Wineries, Olive Oil & Gourmet Lunch or Dinner. The city page groups everything into most popular, highest reviewed, last minute and family-friendly so you can build a day around what actually delivers.
When is the best time to visit Florence?
+
Booking patterns follow the same curve: prices and queues climb in peak weeks, while shoulder season gives you better availability on the top-ranked experiences and more room to change plans.
How many days do you need in Florence?
+
Three full days covers the headline sights without sprinting. A workable rhythm is one anchor experience each morning, such as this one, an unhurried afternoon in a single neighborhood, then a food or nightlife booking in the evening. Five days lets you add a day trip outside the city.
Do I book through Outty or through the operator?
+
Outty ranks and explains the experiences, then hands you to Viator to complete the booking with the operator directly. The price is the same as booking on Viator yourself, and Outty earns an affiliate commission on the referral, which is how the rankings stay free to read.
Ready to lock in your spot?
Pick a date, choose your group, and see the exact price for Private Siena San Gimignano Tour from Florence with Winery Lunch.
Pick your date
