Florence: Siena, San Gimignano Wine Tasting & Lunch Private Tour
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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
4.7/5
Based on 56 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Florence: Siena, San Gimignano Wine Tasting & Lunch Private Tour worth booking?
Florence: Siena, San Gimignano Wine Tasting & Lunch Private Tour is a 9-hour experience in Florence, Italy, from $218 per person. It scores 67 out of 100 on the Outty Ranking, which we label “Solid Choice”, based on a 4.7/5 rating across 56 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 67 / 100
- Rating
- 4.7/5 (56)
- Duration
- 9 hours
- From
- $218 per person
Private Day Trip to Siena and San Gimignano from Florence. On our private Florence day tours of Tuscany enjoy a tour of two among the most iconic Tuscan hill towns — Siena and San Gimignano — as well as a selected winery
What you get
About this experience
Private Day Trip to Siena and San Gimignano from Florence. On our private Florence day tours of Tuscany enjoy a tour of two among the most iconic Tuscan hill towns — Siena and San Gimignano — as well as a selected winery where you'll enjoy wine tasting accompanied by a typical Tuscan lunch
What travelers are saying
Outty’s summary of the themes that recur across 56 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.
Small groups
4 mentionsThe group size is repeatedly described as intimate rather than packed.
Pace and timing
3 mentionsSeveral reviewers found the schedule tight or the day long.
Photo opportunities
2 mentionsThe views and photo stops come up again and again.
Traveler reviews
56 verified traveler reviews for Florence: Siena, San Gimignano Wine Tasting & Lunch Private Tour. Ratings and reviews provided by Viator and Tripadvisor.
Tuscan Towns
Jonathan was the best. He was so kind and informative about the Tuscan region. He made our day so much better. The views were amazing and the towns made you feel like you were stepping back into time… Absolutely beautiful. This tour is well worth doing and we would highly recommend it.
via Tripadvisor
1st Class Service Provider
We were a group of 9 people looking for a customised private tour to Chianti, Siena n San Gimignano. Prior to this, I had booked another small group tour which required us to meet the guide at an inconvenient location and while comparing the cost decided to go with adventure Bellissime which provided door to door hotel pick up service. This was certainly the clincher as I wanted the group to travel in comfort and not having to deal with travelling in a bus/coach with strangers. Our drivers were Giacomo and Gianni, both were polite and friendly. I’d like to give special mention to Giacomo who was my driver, he provided 5 star service throughout. Knowledgeable and friendly and always engaging. For us the highlight was the vineyard tour, Guilia our guide from Casa Emma was very professional and we thoroughly enjoyed the wine tasting and wine pairing. Tasting 6 different types of wines. The food was superb, service was always on point and the whole group has a wonderful time chatting and laughing throughout our meal, taking in the gorgeous view of the vineyard. We over stayed at the vine yard but nonetheless we ended off our tour taking in the breathtaking night view of the beautiful city of Florence as we stopped on the hilltop on our journey back. All in all, we would do this tour a second time round the next time we visit Florence. I would rate my experience with Adventure Bellissime a 5/5. By a country mile the best tour I booked, nothing Viator/getyourguide/withlocals could ever match in terms of service level. ( just for context, I did book tours from those companies I listed and they paled in comparison). This is not a paid review and everything stated here is true and accurate reflection of the authentic and 1st class service we received.
via Tripadvisor
Great Tour Fun Day
This was a terrific tour. Alessandro was our guide. And he was terrific! He was knowledgeable and fun. Siena was really interesting. We stopped by a winery for lunch. Then we headed to San Gimignano. And last stop was Pisa. This was a fun tour! Next time I head to Italy, I will see what other tours these guys provide. It was a great experience!
Response from the operator: Dear Guests, Thank you for providing your 5-star feedback about the Tuscany tour. We are very happy you had a terrific experience and a fun day exploring the wonderful landscapes of Tuscany. Thank you for joining and we hope to welcome you on our tours again in the future! Kind regards, Aleksandra Sales Manager @ Avventure Bellissime
via Tripadvisor
Great tour, lots of extras!
We had the tour from Florence to San Gimignano, Siena and a vineyard in the Chianti region. Our tour leader, Benjamin, was the best ever! Very interesting, so nice and knew a lot about the history of the region. We absolutely loved the whole tour and got a lot out of our money. Benjamin went above and beyond to make our day memorable. Thanks a lot!
Response from the operator: Dear Client , Thank you so much for taking the time to send your feedback about our Small group tour to Siena , San Gimignano and Chianti from Florence . I will of course share you comment with our valuable driver-guide. We are all happy in our organization when clients find their experiences with us exceeding their expectations . This is what makes me so proud of my wonderful Team . Kindest regards , Monica
via Tripadvisor
Day trip to the Chianti Wine region
Loved this trip. Our driver provided information along the way to Siena and San Gimignano. We stopped at a lovely winery for wine tasting - 4 different kinds of wine for taste testing were provided with refills. A delicious traditional Italian lunch was provided. The presenter at the winery nicely described information about the grapes and the wine we had. We stopped at each village. We had a two hour guided tour of Siena. The tour guide was excellent. We had ample time in both villages to explore.
Response from the operator: Dear Marianne, Thank you for the 5-star review, we truly appreciate it! We are very happy our small group tour to Tuscany hill towns and Chianti area with lunch and wine tasting met your expectations and you enjoyed the winery visit, the views and the guided tour in Siena. We look forward to welcoming you on our tours again in the future! Kind regards Aleksandra Sales Dept
via Tripadvisor
Good to know
- Duration
- 9 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Booked in 30 days
- 20
- Verdict
- Solid Choice
Why this scores 67
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Florence: Siena, San Gimignano Wine Tasting & Lunch Private Tour: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Florence.
How much does Florence: Siena, San Gimignano Wine Tasting & Lunch Private Tour cost?
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Prices start at $218 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 Florence: Siena, San Gimignano Wine Tasting & Lunch Private Tour take?
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Plan for about 9 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 Florence: Siena, San Gimignano Wine Tasting & Lunch Private Tour worth it?
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It holds an Outty Ranking of 67 out of 100, which we label "Solid Choice". That score blends traveler sentiment (4.7/5 across 56 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 Florence: Siena, San Gimignano Wine Tasting & Lunch Private Tour?
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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 Florence: Siena, San Gimignano Wine Tasting & Lunch Private Tour suitable for kids and families?
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Yes, all ages are welcome. Families should still weigh the 9-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book Florence: Siena, San Gimignano Wine Tasting & Lunch Private Tour?
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Around 20 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 9-hour experience runs outdoors or after sunset.
Where does Florence: Siena, San Gimignano Wine Tasting & Lunch Private Tour 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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