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!
Larger groups pay less per person.
From the operator’s live schedule on Viator, checked Oct 23.
Drive through the historical downtown
Scenic drives throught the most beautiful roads with stunning views
Time permitting a stop can be included
Enjoy the steep vineyards and olive grooves
The pick up is done directly at your front door: hotels (even if not listed here), vacation rentals, B&B, Apartments, villas, train stations. PLEASE ENTER THE NAME/ADDRESS OF YOUR LODGING AT THE MOMENT OF THE BOOKING TO ALLOW US TO PLAN THE PICK UP AT YOUR FRONT DOOR
Reviews collected by Viator and Tripadvisor
Excurgo comparison of 3,208 Viator tours, recalculated daily.
For a full refund, cancel at least 24 hours before the scheduled departure time.
Exclusive Private Tuscany Wine Tour & Food Pairing Session lasts about 8 hours. The itinerary has 4 stops.
Prices start at $573 per person for this Florence experience, booked through Viator with the price shown before checkout. There is 1 booking option, so the final price depends on the option you choose.
According to the operator’s current schedule, it runs on Mondays, Tuesdays, Wednesdays, Thursdays, and Fridays, starting at 9:30 AM.
Yes. Cancel at least 1 day before the start for a full refund. Later cancellations are non-refundable.
Yes, pickup is offered. The pick up is done directly at your front door: hotels (even if not listed here), vacation rentals, B&B, Apartments, villas, train stations. PLEASE ENTER THE NAME/ADDRESS OF YOUR LODGING AT THE MOMENT OF THE BOOKING TO ALLOW US TO PLAN THE PICK UP AT YOUR FRONT DOOR Pickup points include Hotel Romagna, Hotel Residence La Contessina.
The experience is available in EN, IT.
It is a private experience: only your party takes part. Up to 8 travellers can book together.
Yes, bookings are confirmed instantly.
Travellers rate it 4.9 out of 5 across 72 reviews on Viator and Tripadvisor; it is run by Cooltours.
Reviews collected by Viator and Tripadvisor
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!
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)
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!!!!
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!
Long day lots of driving but through beautiful countryside. Bring water with you. Host was knowledgeable and friendly.
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.
A wonderful day spent with Anna in the Chianti region! We visited several lovely wineries, tasted delicious wine, and ate fabulous food. The scenery was absolutely stunning. Anna is a joy to be around, a fantastic hostess and knowledgeable guide. I would definitely travel with her again!
What an incredible experience visiting the smaller wineries. We had top notch service and our tour from Cool Tours was the best tour we have had on our travels. Thank you to Anna and Cool Tours for a memorable experience. We will use them again on our next trip.
Enjoyed all of our visits, but especially our lunch stop. That vineyard and family was amazing. We felt they enjoyed it as much as we did. And along with the atmosphere and views, the food (and wine) was awesome.
Thank you so much for taking the time to write about your experience! I hope we’ll have the opportunity to host you again.
Wonderful time! All the wineries were welcoming and a little bit different and Max our driver was amazing and so knowledgeable!
I can't recommend Anna (Cool Tours) enough, she was perfect - exactly what we were hoping for when we were planning a wine tour in Tuscany. We booked 2 tours with Cool Tours; one day was a tour of D'Orcia with stops at Pienza, Montepulciano and a winery. The next day was a tour of Chianti Classico with stops at 2 wineries and San Gimignano. Anna was wonderful! boundless energy, fun, knowledgeable - she made the trip so enjoyable. We had a great time with her. One of the days she was booked up but she managed to get us another driver, Cristiano, who was also great and accommodating. These were private tours, just the 4 of us in our party, so we weren't dealing with sharing our experience with strangers. Anna has relationships with high quality, smaller wineries that provide special attention to their guests. We were treated to a private tour, tasting and lunch. We purchased a case at each winery and had it shipped back to New York, no problems (wine arrived within 2-4 weeks). If you are considering a private tour (wine or otherwise) in Tuscany, Anna is the best choice in my opinion.
| Tour | Duration | Rating | Price | |
|---|---|---|---|---|
| Exclusive Private Tuscany Wine Tour & Food Pairing Session | 8 hours | 4.9 (72) | $573 | |
 Private Top Brunello Montalcino Wine Tour & Food Pairing Session | 10 hours | 5.0 (18) | $573 | View |
 Guided Wine Walk in Florence with 3 Wine Pairing and Food Tasting | 3 hours | 5.0 (21) | $79 | View |
 Natural wine & Veggy food pairing in a bookstore in Florence | 2 hours | 5.0 (1) | $184 | View |
 Italian Charcuterie & Cheese Board with Wine or Beer Pairing | 1 hour | 4.5 (17) | $52 | View |
 Florence Exclusive PRIVATE Food Tour with 6 or 10 Tastings | 3 hours | 4.7 (681) | $131 | View |
 Private Tuscany Horse Ride, Wine Tasting and local food at Estate | 5h 30min | 5.0 (56) | $367 | View |