San Gimignano and Chianti Classico Wine and Food PRIVATE TOUR from Florence
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September 2026
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Adults
Age 13 and over
Children
Age 12 and under
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Non-refundable booking. Same price on Viator, Outty earns a commission.
Traveler rating
5.0/5
Based on 8 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is San Gimignano and Chianti Classico Wine and Food PRIVATE TOUR from Florence worth booking?
San Gimignano and Chianti Classico Wine and Food PRIVATE TOUR from Florence is a 8-hour experience in Florence, Italy, from $170 per person. It scores 54 out of 100 on the Outty Ranking, which we label “Worth a Look”, based on a 5/5 rating across 8 reviews. This booking is non-refundable, so pick your date carefully. Same-day spots are currently showing.
- Outty Ranking
- 54 / 100
- Rating
- 5/5 (8)
- Duration
- 8 hours
- From
- $170 per person
* Private, Exclusive, Customizable, door-to-door tour of San Gimignano and Chianti Classico, wine and food Tour from Florence * 8 hours in a luxury Mercedes sedan/minivan with air conditioning and knowledgeable English
What you get
About this experience
* Private, Exclusive, Customizable, door-to-door tour of San Gimignano and Chianti Classico, wine and food Tour from Florence * 8 hours in a luxury Mercedes sedan/minivan with air conditioning and knowledgeable English speaking driver * Free Wi-Fi on board * Refreshments on board * Gas - Tolls - VAT
What travelers are saying
Outty’s summary of the themes that recur across 8 traveler reviews. Written by us, not quoted from reviewers.
The guide
4 mentionsTravelers single out the guide as the reason the experience works.
Knowledge and storytelling
4 mentionsReviewers describe the commentary as informative rather than scripted.
Photo opportunities
3 mentionsThe views and photo stops come up again and again.
Food and drink
3 mentionsThe tastings and food stops are a highlight for most reviewers.
Organization
2 mentionsPickup, timing, and logistics are described as running smoothly.
Small groups
2 mentionsThe group size is repeatedly described as intimate rather than packed.
Traveler reviews
8 verified traveler reviews for San Gimignano and Chianti Classico Wine and Food PRIVATE TOUR from Florence. Ratings and reviews provided by Viator and Tripadvisor.
Wonderful way to see Tuscany
Roberto was an amazing host. He was personable, knowledgeable and easy to talk to. He gave a lot of history of the areas we visited which made the experience that much better.
via Tripadvisor
Book with We Drive You!
We had the absolute pleasure of spending three days in Tuscany with our driver Bruno, and we cannot recommend him highly enough! Our group of six women felt completely comfortable and well taken care of from the moment we met him. Bruno was not only punctual and professional, but also incredibly knowledgeable about the region. He shared so many great insights about the history, culture, and hidden gems of Tuscany, which truly enriched our experience. Bruno showed us all the best spots—including charming villages, scenic viewpoints, and unforgettable wineries. His recommendations were spot-on and gave us a real taste of the beauty and spirit of the region. What made our time with Bruno even more special was his wonderful personality—he was friendly, fun, and had a great sense of humor. He was always willing to go the extra mile to ensure we were enjoying ourselves and making the most of our trip. He was also incredibly accommodating—for example, he looked out for our well-being by protecting us from the bees every morning and afternoon at our Airbnb, and he was quick to assist with all the luggage we had between the six of us! If you're looking for a reliable, personal, and informative driver in Tuscany, Bruno is the one! Thank you, Bruno, for helping make our trip so memorable!
Response from the operator: We are very happy to hear that Bruno looked after you so well and made your stay in our beautiful land memorable.
via Tripadvisor
Perfect tour! Highly recommend
Kosmo drove us throughout the Chianti Region. The trip was well planned with lots of great stops + Kosmo shared his vast knowedge of the area along the way. Highly recommend!! Thanks Kosmo!!
Response from the operator: We are delighted to hear that the day went well!
via Tripadvisor
Worth it!
I am so glad I booked a private driver with We Drive You in Tuscany! I had multiple quotes from various companies and I went with this company. Easy and very communicative from the beginning. I booked a private driver with tours for two days with a car seat for my toddler. Our driver was, Roberto for both days. Roberto was so kind and friendly! We truly enjoyed his conversation. We learned so much from him about Italy and the Tuscan region, so many fun facts! He gave us great recommendations about the little towns we visited. He helped with our toddler and our toddler enjoyed his entertainment as well. Worth every penny. I highly recommend this company. I would book with them again if I am ever back in Tuscany!
Response from the operator: We are delighted to hear that Roberto made your time in Tuscany special and even your toddler enjoyed his company!
via Tripadvisor
The best way to explore Tuscany!
If you are looking for a private, guided day trip around Tuscany, you can’t beat We Drive You Tuscany! Our driver Roberto was so kind and knowledgeable, and planned the most fabulous day for us in Chianti. He picked us up in the morning at our hotel in Tuscany and took us to visit San Gimignano, where we were able to spend a few hours exploring on our own. Once we were finished, he picked us up at the village gates and took us to Sant’Agnese Farm, where we had one of the most incredible meals of our entire trip. Along with the delicious meal that was cooked from scratch by the winery owner, we got to tour their beautiful property and try all of their amazing wines and balsamic vinegars, which were all so delicious. Finally, we ended the day with one more tasting at Agriturismo Rocca, which was incredibly charming and complete with breathtaking views, delicious wine, and the most amazing olives I have ever had. In addition the wonderful stops and wine, Roberto really made our day special. He shared so much history and information about the region with us and really made us feel like we were part of his family. If you are looking for an easy, carefree, and intimate way to explore the Tuscan region, then We Drive Tuscany is a must! Ask for Roberto!!
via Tripadvisor
Good to know
- Duration
- 8 hours
- Free cancellation
- Non-refundable
- Minimum age to book
- All ages
- Availability
- Bookable today
- Booked in 30 days
- 3
- Verdict
- Worth a Look
Why this scores 54
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
San Gimignano and Chianti Classico Wine and Food PRIVATE TOUR from Florence: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Florence.
How much does San Gimignano and Chianti Classico Wine and Food PRIVATE TOUR from Florence cost?
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Prices start at $170 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 San Gimignano and Chianti Classico Wine and Food PRIVATE TOUR from Florence 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 San Gimignano and Chianti Classico Wine and Food PRIVATE TOUR from Florence worth it?
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It holds an Outty Ranking of 54 out of 100, which we label "Worth a Look". That score blends traveler sentiment (5/5 across 8 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable food & drink in Florence, and how flexible the cancellation terms are.
Can I cancel or reschedule San Gimignano and Chianti Classico Wine and Food PRIVATE TOUR from Florence?
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No. This experience is sold on a non-refundable basis, so only book a date you are confident about. Similar experiences in the city do offer free cancellation if flexibility matters more than price.
Is San Gimignano and Chianti Classico Wine and Food PRIVATE TOUR from Florence 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 San Gimignano and Chianti Classico Wine and Food PRIVATE TOUR from Florence?
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Around 3 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 San Gimignano and Chianti Classico Wine and Food PRIVATE TOUR from Florence 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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