Exclusive Private Tuscany Wine Tour & Food Pairing Session
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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
4.9/5
Based on 72 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Exclusive Private Tuscany Wine Tour & Food Pairing Session worth booking?
Exclusive Private Tuscany Wine Tour & Food Pairing Session is a 8-hour experience in Florence, Italy, from $290 per person. It scores 72 out of 100 on the Outty Ranking, which we label “Strongly Recommended”, based on a 4.9/5 rating across 72 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 72 / 100
- Rating
- 4.9/5 (72)
- Duration
- 8 hours
- From
- $290 per person
ALL INCLUDED PRIVATE WINE TOUR to 3 selected wineries of Tuscany mainly around the prestigious Chianti Classico area. Wineries are selected by a LEVEL 3 sommelier aiming to let you enjoy high quality wines in a non-comme
What you get
About this experience
ALL INCLUDED PRIVATE WINE TOUR to 3 selected wineries of Tuscany mainly around the prestigious Chianti Classico area. Wineries are selected by a LEVEL 3 sommelier aiming to let you enjoy high quality wines in a non-commercial setting. Each winery has a unique character in its location, views, undergrounds. Usually your hosts are the winery’s owners sharing their lives and winemaking skills. Wine pours are generous and they usually include Supertuscan wines. Tastings include extra virgin olive oil, and if locally made also balsamic. Lunch is based on food & wine pairing session at one winery. You’ll be escorted by a professional and yet friendly driver-guide, specialized in wine-making (ranging from Level 1 to Level 3 Sommelier), English speaking and knowledgeable about the history of the area. All vehicles are prestigious minivans with all comforts. No food and alcoholic drinks are allowed in the vehicles during the drive. We highly recommend to have breakfast before the tour!
What's included
Included
- Hotel pickup and drop-off
- All taxes, fees and handling charges
- Wine tasting Fees at all the three selected wineries
- Driver/guide
- Full lunch at one winery for food and wine pairing
- Transport by air-conditioned minivan
Not included
- Gratuities
- Breakfast
What you'll see and do
Florence
Drive through the historical downtown
Pass by without stopping
Strada Statale 222 Chiantigiana
Scenic drives throught the most beautiful roads with stunning views
Pass by without stopping
Castellina In Chianti
Time permitting a stop can be included
Pass by without stopping
Radda in Chianti
Enjoy the steep vineyards and olive grooves
Pass by without stopping
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, it
- Ticket
- Mobile Only
- Runs on
- Mon, Tue, Wed, Thu, Fri
- Group size
- Up to 8 travelers per booking
- Operated by
- Cooltours
Know before you go
- Public transportation options are available nearby
- Not recommended for pregnant travelers
- Suitable for all physical fitness levels
- Dress code is smart casual
- Please advise any specific dietary requirements at time of booking
- Vegetarian and vegan options available, please advise in the notes at time of booking
- Minimum drinking age is 18 years
- Food and Alcohol are not allowed inside the vehicles
- Breakfast before the tour pick up is highly recommended
- Possibility to buy wines directly from the wineries
Photos
What travelers are saying
Outty’s summary of the themes that recur across 72 traveler reviews. Written by us, not quoted from reviewers.
Food and drink
8 mentionsThe tastings and food stops are a highlight for most reviewers.
Knowledge and storytelling
6 mentionsReviewers describe the commentary as informative rather than scripted.
The guide
4 mentionsTravelers single out the guide as the reason the experience works.
Good for families
3 mentionsReviewers traveling with kids report it landed well with their group.
Small groups
3 mentionsThe group size is repeatedly described as intimate rather than packed.
Photo opportunities
2 mentionsThe views and photo stops come up again and again.
Traveler reviews
72 verified traveler reviews for Exclusive Private Tuscany Wine Tour & Food Pairing Session. Ratings and reviews provided by Viator and Tripadvisor.
The Best of the Best!
This was our 3rd trip with Anna (2019, 2023 and 2026) and as always she delighted us with new wineries to discover! She has wonderful relationships in the area and you know immediately that she is loved by the wine partners. We had 3 wonderful days with her --- she mixes the day with fun along with her in-depth knowledge of wine and the region. She is the best!
via Tripadvisor
Bravo Maximo!
Our driver Maximo was magnificent, he’ll have you laughing the whole way! Couldn’t recommend him more highly. The tastings themselves were excellent picks, you truly feel immersed in the Tuscan countryside and get one on one time with the winemakers and their families. More cozy, intimate, and down to earth than anything we did in Napa. Just come hungry! (And thirsty)
via Viator
Unforgettable wine tasting experience
Anna is THE BEST. She’s knowledgeable, personable, funny, prompt and very well connected. Every minute of our time with Anna was an experience. We learned, we laughed, we loved every second. Anna pours he soul into making your experience unforgettable. Oh and did I mention she’s a sommelier so unless we were talking to the winemaker we were finding Anna outmatched all of our wine tour hosts lol! Thank you so much!!!!
via Tripadvisor
Wonderful wine tour in Tuscany
Our family of four spent a wonderful day with Anna. She picked us up very close to our apartment in Florence in her comfortable van and we visited two small-production wineries, one where we had a private tour of the vineyard and winery and one where we enjoyed an absolutely delicious lunch served by the winery owners. Both served excellent wines typical of the Chianti region, and we are anxiously awaiting our shipment of wines that we ordered from each! After lunch, Anna drove us to San Gimignano where she dropped us off to wander and shop for about an hour. One of my 18-year-olds fully embraced the wine tasting and loved all the wines; the other hasn't acquired a taste for wine but still loved every minute of the day. This outing was a highlight of our three weeks in Italy... I highly recommend Anna's company if you're looking for a special day in Tuscany!
via Tripadvisor
Long day lots of driving...
Long day lots of driving but through beautiful countryside. Bring water with you. Host was knowledgeable and friendly.
Response from the operator: Dear Enrico, thank you so much for sharing your experience and taking the time to write a review. We’re surprised about the long drive as the wine region we covered was one hour to the first winery, and then around 30 minutes to the second and less than 15 minutes to the last. Clearly the drive between wineries are in the scenic roads so to enjoy the views, the landscape as part of the overall experience as you stated somehow. Going to different and selected places makes the difference compared to other type of tours. About the water, we encourage clients to bring their refillable bottles to avoid plastic trash as well as to avoid waste of water cause when it gets warm we end up with open bottles almost full that have to be thrown away. Anyway we’ll make sure future clients will know about that as well.
via Viator
Good to know
- Duration
- 8 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Mon, Tue, Wed, Thu, Fri
- Price range
- $290 to $500
- Hotel pickup
- Included for all travelers
- Booked in 30 days
- 25
- Verdict
- Strongly Recommended
Why this scores 72
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Exclusive Private Tuscany Wine Tour & Food Pairing Session: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Florence.
How much does Exclusive Private Tuscany Wine Tour & Food Pairing Session cost?
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Prices start at $290 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 Exclusive Private Tuscany Wine Tour & Food Pairing Session 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 Exclusive Private Tuscany Wine Tour & Food Pairing Session worth it?
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It holds an Outty Ranking of 72 out of 100, which we label "Strongly Recommended". That score blends traveler sentiment (4.9/5 across 72 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 Exclusive Private Tuscany Wine Tour & Food Pairing Session?
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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 Exclusive Private Tuscany Wine Tour & Food Pairing Session 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 Exclusive Private Tuscany Wine Tour & Food Pairing Session?
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Around 25 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 Exclusive Private Tuscany Wine Tour & Food Pairing Session 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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