Private Top Brunello Montalcino 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
5.0/5
Based on 18 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Private Top Brunello Montalcino Wine Tour & Food Pairing Session worth booking?
Private Top Brunello Montalcino Wine Tour & Food Pairing Session is a 10-hour experience in Florence, Italy, from $290 per person. It scores 67 out of 100 on the Outty Ranking, which we label “Solid Choice”, based on a 5/5 rating across 18 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 67 / 100
- Rating
- 5/5 (18)
- Duration
- 10 hours
- From
- $290 per person
ALL INCLUDED wine tour to visit three boutique and awards winning wineries selected by level 3 sommelier Anna and it's an all included experience. This tour includes a visit to all the three wineries to enjoy the cellars
What you get
About this experience
ALL INCLUDED wine tour to visit three boutique and awards winning wineries selected by level 3 sommelier Anna and it's an all included experience. This tour includes a visit to all the three wineries to enjoy the cellars and to learn more about the wine making process from scratch. Duration of the cellar tour adapted to clients’ request. Each tasting includes some snacks, extra virgin olive, others. For lunch please advise about allergies and severe food intolerances.The selection is based on the quality of the wines, the location on the different slopes of the hills, the different terroir, and use of the barrels. Brunello di Montalcino is the top end wine of Tuscany so we’ll provide a unique and intimate opportunity to sample the best products through an authentic experience by visiting non commercial producers. We highly recommend you to have breakfast before the tour and not to book other activities the same day of this tour due to the overall length of the day.
What's included
Included
- Hotel pickup and drop-off
- All taxes, fees and handling charges
- Driver/guide
- Transportation in air conditioned Mercedes
- Strictly private tour
- Full lunch based on local products for wine pairing
- Wine tastings fees at 3 wineries
Not included
- Gratuities
- Alcoholic beverages
What you'll see and do
Florence
Drive through the historical downtown learning interesting facts about the city.
Pass by without stopping
Asciano
Soft rolling hills with cypress trees, farmhouses and a lunar atmosphere made of clay....the desert of Accona as defined by Dante Alighieri
Pass by without stopping
Walled village along the medieval road pilgrims used to follow to go to Rome, Jerusalem, or Canterbury and Santiago de Compostela
Pass by without stopping
Montalcino
Enjoy the views, the fortress, the hills surrounded by olive grooves and vineyards. Time permitting it will be possible to stop in the hilltop town.
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 or vegan options available, please request in the notes at the time of booking
- Minimum drinking age 18 years
- Drinking alcohol inside the vehicles is not allowed
- Breakfast before the tour is recommended
Photos
What travelers are saying
Outty’s summary of the themes that recur across 18 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
4 mentionsReviewers describe the commentary as informative rather than scripted.
Good for families
4 mentionsReviewers traveling with kids report it landed well with their group.
Small groups
2 mentionsThe group size is repeatedly described as intimate rather than packed.
Traveler reviews
18 verified traveler reviews for Private Top Brunello Montalcino Wine Tour & Food Pairing Session. Ratings and reviews provided by Viator and Tripadvisor.
Best Brunello Tour you will find
Ana is amazing. She is hilarious, fun, and really knows her wine. The places we stopped were fantastic in regards to both wine and food pairings. Highly highly recommend. If we are ever back in the area, we will book her again.
via Viator
Excellent wine, gorgeous setting, family friendly
We really enjoyed the family wineries that were chosen as a part of this tour. We learned a lot about Brunellos and other wines of the Montalcino region. The day was truly memorable and the food and wines were delicious. Max was an amazing host. Highly recommend this tour. My husband and I loved it!
Response from the operator: Dear Kimberly thank you so much for taking the time to write about your experience! I’m happy you enjoyed the wineries I have selected and I hope we’ll have the opportunity to meet next time!
via Viator
Awesome Two Days With Anna Cool Tours!
This was the second and third time we toured with Anna in the Tuscan wine country. We first worked with Anna in the fall of 2019 in the Chianti Classico area. We had such a wonderful time with Anna and loved her personality that we easily chose to spend two full days with her in the Brunello di Montalcino area enjoying some delicious brunellos, roso di Montalcino and some wonderful homemade food at 2 wineries. We stayed in downtown Florence for our trip and Anna picked us up on time each of the two days. The drive to Montalcino from Florence takes a bit of time but driving with Anna is goes by quickly! The conversation around wine, Tuscany, food, tourism, Siena...anything you want to discuss! You see some beautiful hill towns on the way to Montalcino. The wineries Anna works with and the people are wonderful. No problem if you don't speak Italian, almost everyone speaks English. Anna will interpret if need be. The wines are terrific! These are not Tuscan wines you will find at your local wine store back home. This are more boutique wineries of special care and passionate people. Each winery will gladly ship your wine to you as you desire. Or, you can bring your own wine luggage like I did. This is a very special experience with a very special person in Anna! We tell everyone about her. In fact, we are coming back in the Fall of 2022 and plan to work with Anna again with tours to Montalcino (again) and Nobile di Montepulciano. We have been going to Italy since 1999 and I can easily say Anna's tours are the most well thought out, considerate, fun and interesting I have taken. She cares about her clients and wants to get to know you before and during the tours so she can provide you with what you expect but to also exceed your expectations.
Response from the operator: Thank you so much for taking your precious time to write about your experience! I'm very looking forward to seeing you again here in Tuscany and taste some more delicious wines!!!
via Tripadvisor
The best!
We could not recommend Anna enough! She was so fantastic. Her knowledge of the area and the history of Tuscany was such an added bonus to our day touring wineries. She very much tailored the tour for our wants and needs. We will definitely use her again if we have the opportunity!
Response from the operator: Thank you so much for sharing your personal experience here! I had a great day meeting up with you and I really hope we'll have the chance to meet again and taste more wines too.... Ciao!
via Tripadvisor
Anna and her tours are both cool!
Anna was great. My family of four visited Tuscany for a week in 2018. I had a rented car, but preferred to let her drive and be our guide. She had vast knowledge of wine, country, history and culture. You will count yourself lucky to find such a great and accommodating guide. Highly recommended. Don't hesitate. She will make your trip both memorable and easy. After all, that's her job and she does it well. Cool! Her van fits places those big tour buses do not, FYI.. I sent a case of Brunello home. I am so glad I did, but wish I'd sent two!
via Tripadvisor
Good to know
- Duration
- 10 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
- 6
- Verdict
- Solid Choice
Why this scores 67
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Private Top Brunello Montalcino Wine Tour & Food Pairing Session: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Florence.
How much does Private Top Brunello Montalcino 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 Private Top Brunello Montalcino Wine Tour & Food Pairing Session take?
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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 Top Brunello Montalcino Wine Tour & Food Pairing Session 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 (5/5 across 18 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable most popular in Florence, and how flexible the cancellation terms are.
Can I cancel or reschedule Private Top Brunello Montalcino 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 Private Top Brunello Montalcino Wine Tour & Food Pairing Session suitable for kids and families?
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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 Top Brunello Montalcino Wine Tour & Food Pairing Session?
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Around 6 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 10-hour experience runs outdoors or after sunset.
Where does Private Top Brunello Montalcino 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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