
Private Tour to Siena and San Gimignano with Wine Tasting & Lunch
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September 2026
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Adults
Age 13 and over
Children
Age 12 and under
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Free cancellation up to 24 hours before. Same price on Viator, Outty earns a commission.
Traveler rating
4.8/5
Based on 20 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Private Tour to Siena and San Gimignano with Wine Tasting & Lunch worth booking?
Private Tour to Siena and San Gimignano with Wine Tasting & Lunch is a 8-hour experience in Florence, Italy, from $490 per person. It scores 58 out of 100 on the Outty Ranking, which we label “Worth a Look”, based on a 4.8/5 rating across 20 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 58 / 100
- Rating
- 4.8/5 (20)
- Duration
- 8 hours
- From
- $490 per person
Exclusive Private Full day Tour available from Florence or Livorno with visits on your own of these two typical Medieval towns in Tuscany region. Discover with us what's there to see beyond the big and famous cities of R
What you get
About this experience
Exclusive Private Full day Tour available from Florence or Livorno with visits on your own of these two typical Medieval towns in Tuscany region. Discover with us what's there to see beyond the big and famous cities of Rome & Florence, and take a "Day Trip" to see the real Italy in the Chianti region.
What's included
Included
- Private tour
- All taxes, fees and handling charges
- Wine tasting
- Driver/guide
- Lunch
- Hotel/port pickup and drop-off
- Transport by private vehicle
Not included
- Alcoholic drinks (available to purchase)
- Souvenir photos (available to purchase)
What you'll see and do
Acquario Di Livorno
We depart from the cruise pier in Livorno or any hotel in Florence.
Pass by without stopping
Piazza del Campo
Enjoy Siena on your own
60 minutes here
San Gimignano 1300
Enjoy San Gimignano on your own
60 minutes here
Tenuta Torciano
Enjoy this fantastic local winery, as your location for both lunch & wine tastings, just 5 minutes outside of the medieval town of San Gimignano.
120 minutes here · Admission included
Where it starts and ends
Hotel pickup
Pickup is included for all travelers. Pickup begins about 5 minutes before departure.
Before you book
- Cancellation
- For a full refund, cancel at least 24 hours before the scheduled departure time.
- Languages
- en
- Ticket
- Mobile Only
- Runs on
- Every day
- Group size
- Up to 8 travelers per booking
- Operated by
- Touring Italy - Roberto D'Alessandro
Know before you go
- Not recommended for travelers with spinal injuries
- Not recommended for travelers with poor cardiovascular health
- Not recommended for pregnant travelers
- Specialized infant seats are available
- Travelers should have at least a moderate level of physical fitness
- Wheelchair accessible
- Minimum drinking age is 18 years
- Dress code is smart casual
Photos






What travelers are saying
Outty’s summary of the themes that recur across 20 traveler reviews. Written by us, not quoted from reviewers.
The guide
9 mentionsTravelers single out the guide as the reason the experience works.
Food and drink
7 mentionsThe tastings and food stops are a highlight for most reviewers.
Good for families
3 mentionsReviewers traveling with kids report it landed well with their group.
Knowledge and storytelling
2 mentionsReviewers describe the commentary as informative rather than scripted.
Photo opportunities
2 mentionsThe views and photo stops come up again and again.
Value for money
2 mentionsTravelers feel they got more than they paid for.
Traveler reviews
20 verified traveler reviews for Private Tour to Siena and San Gimignano with Wine Tasting & Lunch. Ratings and reviews provided by Viator and Tripadvisor.
Wine tasting was great. The driver was nice, but he was just a driver who dropped us off in the towns. There was no tour
Wine tasting was great. It was not a tour, we just had a nice car drop us off to explore on our own. This was not what I was expecting.
Response from the operator: Dear Teri, We thank you very much for choosing our tour and for sharing your feedback. We are glad to know that you have enjoyed the wine tastings although we are sorry to hearing that you were expecting something different. We instruct our drivers to provide guests with tips, information, and brief description of what you can do while visiting the towns on your own. A guide is not included so this tour entails free time to stroll around. We apologies for not being able to provide you with the experience you were expecting. We do hope we will be given another chance in the future to prove you that our travel services are worth five stars. Thanks so much for your time taken to write us your feedback.
via Tripadvisor
Touring Italy is an amazing company
My family and I Went to Italy over the past 2 1/2 weeks and had an absolutely amazing time. I think it went so well because we utilized a company called touring Italy to help us with our land & sea transportation as well as several excursions thru-out our trip. The gentleman that owns it is Roberto D’Alessandro. Everything that he suggested and put together for us worked out great. All of the people that he utilized for our journey, were extremely professional and always on time. That says a lot about a company and the man behind the company. The long and short of it is that all of the people that he utilized for our journey, we’re extremely professional and always on time. That says a lot about a company and the man behind the company. The long and short of it is that I would recommend them to anybody considering outside help rather than doing it on your own.
Response from the operator: Dear Tony, we are glad to hearing from you safe and sound back home! We are so happy and indeed very proud for your reviews, and most importantly for what they mean, which is you guys having a fantastic vacation, made unforgettable family moments and yes it is nice to see our work being recognized. Thanks so much for choosing Touring Italy and for bringing your whole family here. We appreciate it your trust in us and we are grateful for your kind words. We look forward to welcoming you back soon for other great travel experiences together. Best Regards, Roberto D'Alessandro Touring Italy.
via Tripadvisor
Had a great time. The...
Had a great time. The Driver was very nice and provided great information about the area. Wish there was more time to enjoy the towns. The Winery was pretty, but maybe a little too touristy.
Response from the operator: Dear Paiyal, Thanks so much for choosing Touring Italy and for sharing your experience with us on TripAdvisor. We are happy you enjoyed the tour, although we would have been heppier if you rated it 5*****. We would appreciate it if you could share with us the reasons why the winery was too touristy. Thanks so much for your time and and for choosing Touring Italy! We look forward to welcome you back for other tours. Best Regards, Roberto D'Alessandro Touring Italy.
via Viator
Great Day in Tuscany
My family had a wonderful day on this tour! The suggested itinerary in the Viator description was good, and our driver Carlo gave suggestions and personal touches that made the day absolutely perfect. The Tenuta Torciano winery was a medium sized vineyard with a delicious 3 course meal, and a chance to taste 7 different wines. The car we rode around with was clean and spacious. Exactly what our family of 4 needed to explore the Tuscan region.
Response from the operator: Dear Ariana, We are so happy to hearing that you had a fabulous day in Tuscany with Touring Italy! Your feedback is so precious and appreciated. We thank you and your family for coming out touring with us and we look forward to welcoming you back soon for other tours! Best Regards, Roberto D'Alessandro Touring Italy.
via Viator
Touring Italy created the most memorable experience for our family!
I cannot recommend Roberto and Touring Italy enough! He created a trip beyond our expectations. He took all of the stress out of planning and scheduling, but more importantly he connected us with the best guides in all of Italy. It was incredible to learn about the history, culture, and food though a local and an expert. Each perfectly personalized everything, and kept our girls well engaged. In Florence, Elena was fantastic. She knew so much, so many people and would take us into little shops to meet a local artisan who was so special because of their craft. She immersed us into the Florentine culture, something we never would have been able to do without her. I think she’s a celebrity too, because everyone seemed to know her and love her 😊. She was beyond fantastic at guiding us through the Accademia, Pitti, Boboli gardens, Uffizi and the walk through the city to taste all of the amazing food. We even went back to the lunch restaurant for dinner because it was so good. Thanks to you, we were so fortunate to have her as our guide! Our driver though Tuscany, Maximiliano, was also fantastic, he was very professional, guided us through the beautiful countryside and explained the history of the towns and buildings. He stopped for perfect photo opportunities and also made good recommendations for gelato and shops. We thoroughly enjoyed our time at Tenuta Torciano. Their wines were fantastic as well as the food. It’s a beautiful winery and Luca was the perfect host. Not only did we do the tasting, he brought additional wines to sample and spent time with us, we felt like special guests. In Rome, we enjoyed our time with Elena, learning about the Forum, Palatine Hill and Colosseum. She was also knowledgeable and was able to connect the past with the current time by showing us ruins and then pictures of how it might have looked before. And lastly, Christiaan was phenomenal as well. We learned about the history, art and architecture. It was so so crowded and he navigated us well, taking us to the most significant places and best views of everything including the Sistine Chapel and St Peters Basillica. Like Elena in Florence he was an expert in everything, explaining things through stories. Even my youngest who doesn’t love museums enjoyed his and her tours. I cannot thank Roberto enough for creating this experience and new family memories. We will always cherish this trip - especially the time with Elena and Christiaan. I will absolutely recommend Touring Italy to anyone traveling to Italy. We are hoping to travel to Southern Italy in the future, and will absolutely us Roberto when time to plan!
Response from the operator: Dear Mrs. Erin Modrow, Thanks so much for choosing Touring Italy and for sharing your experience with us. We are so happy you enjoyed every guide and each moment of the travel experiences we have provided. We are delighted to hearing we will be forever part of your fond memories of Italy, this is the ultimate goal and what drives us everyday to exceed our guests expectations. Thanks so much for your time and we look forward to welcome you all back! Best Regards, Roberto D'Alessandro Touring Italy.
via Tripadvisor
Good to know
- Duration
- 8 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Every day
- Hotel pickup
- Included for all travelers
- Booked in 30 days
- 7
- Verdict
- Worth a Look
Why this scores 58
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Private Tour to Siena and San Gimignano with Wine Tasting & Lunch: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Florence.
How much does Private Tour to Siena and San Gimignano with Wine Tasting & Lunch cost?
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Prices start at $490 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 Tour to Siena and San Gimignano with Wine Tasting & Lunch take?
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Plan for about 8 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 Tour to Siena and San Gimignano with Wine Tasting & Lunch worth it?
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It holds an Outty Ranking of 58 out of 100, which we label "Worth a Look". That score blends traveler sentiment (4.8/5 across 20 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 Tour to Siena and San Gimignano with Wine Tasting & Lunch?
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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 Tour to Siena and San Gimignano with Wine Tasting & Lunch suitable for kids and families?
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Yes, all ages are welcome. Families should still weigh the 8-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book Private Tour to Siena and San Gimignano with Wine Tasting & Lunch?
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Around 7 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?
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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 8-hour experience runs outdoors or after sunset.
Where does Private Tour to Siena and San Gimignano with Wine Tasting & Lunch start and how do I get there?
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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?
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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?
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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?
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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?
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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.
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