Exclusive Private Tuscany Wine Tour & Food Pairing Session
Recommended by 97% of travelers
Badge of Excellence
Florence, Italy
- 8 hours (approx.)
- Pickup offered
- Group discounts
- Mobile ticket
- Offered in: English
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Overview
Experience Tuscany's wine culture on this private wineries tour. Ideal for travelers based in Florence, explore beyond the city without having to hire a car. Travel with a knowledgeable sommelier guide through rolling hills and vineyards, visiting three estates to sample regional wines and olive oil. Enjoy a traditional Tuscan lunch at a family-owned winery paired with wine. Perfect for food lovers looking to immerse themselves in local flavors.
- Take the guesswork out of choosing wineries with sommelier guide
- Enjoy a personalized experience on this private tour
- Escape the busy city and relax in the Italian countryside
- Don't worry about getting hungry, with an included lunch
Sample Menu
Starter
Antipasto Toscano
Main
Pasta
Dessert
Cake, sweets or biscotti and Vin Santo
What's Included
- All taxes, fees and handling charges
- Full lunch at one winery for food and wine pairing
- Wine tasting Fees at all the three selected wineries
- Driver/guide
- Transport by air-conditioned minivan
- Hotel pickup and drop-off
- Gratuities
- Breakfast
Meeting and Pickup
Pickup points
Select a pickup point
Pickup details
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
Start time.9:30 am
Itinerary
Florence (Pass By)
Strada Statale 222 Chiantigiana (Pass By)
Castellina In Chianti (Pass By)
Radda in Chianti (Pass By)
Additional Info
- Confirmation will be received at time of booking, unless booked within 6 days of travel. In this case confirmation will be received within 48 hours, subject to availability
- Not wheelchair accessible
- Near public transportation
- Not recommended for pregnant travelers
- Most travelers can participate
- 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
- This is a private tour/activity. Only your group will participate
Supplied by
Cancellation Policy
You can cancel up to 24 hours in advance of the experience for a full refund.
Traveler Photos
Reviews
4.9
based on 72 reviews
Sort by: Most insightful
Ben_G, May 2026
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)
enrico_C, Jun 2025
Long day lots of driving but through beautiful countryside. Bring water with you. Host was knowledgeable and friendly.
Response from Host, Jun 2025
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.
Mary_L, Oct 2024
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.
Jeffrey_H, Aug 2024
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.
Response from Host, Aug 2024
Thank you so much for taking the time to write about your experience! I hope we’ll have the opportunity to host you again.
Jane_S, Nov 2023
Excellent hosts at each winery. Especially Alessandro at Casa Sola.
Fabulous lunch at Querceto Di Castellina.
Great wines all around.
Our Driver, Max, was prompt, courteous, cheerful— and provided interesting historical and geographical details as we drove through the scenic countryside.
Response from Host, Nov 2023
Hi Jane thank you so much for taking the time to share your experience! I’m very happy you enjoyed the wine selection done by us and we’re looking forward to seeing you again.
Alexandria_A, Jul 2023
Anna was the best guide we could of asked for! She was so knowledgeable about the area and all the wines. She was a incredible guide and so friendly! Highly highly recommend and will be using her and her company when we come back.
Lauren_W, Jul 2023
Anna was incredible, from the moment I booked the trip she was so quick to respond to questions (and worries!), and when she picked us up I instantly felt at ease (after a so-far stressful trip!). Anna was a turning point in my vacation and I am so grateful to her (and her amazing selection of wineries!!). This was such a special trip, and Anna is just amazing at what she does. I can’t imagine a winery tour that would have been better.
THANK YOU ANNA ❤️
Response from Host, Jul 2023
Thank you so much for writing about the tour!!! I had a blast meeting you and being part of your memories!!!
Stress-free is my goal and I’m looking forward to seeing you again soon for new adventures ❤️ hugs to the best chemist ever 😉
Brett_L, Jun 2023
This was absolutely the best part of our entire trip to Italy. First off, Anna was our tour guide and I can’t stress enough how great she was. She really made the trip the best. Then the selection of vineyards is great. We experienced a very small family run vineyard where we had lunch and were very welcomed. Before that was a small-medium sized vineyard where the owner walked us around. And lastly was a slightly larger vineyard, which was very nice and a great way to finish.
Everything about this trip was exactly what we were hoping for. The views driving between are also breathtaking. Anna knows the more scenic routes to take. Highly highly recommend this tour to anyone.
Response from Host, Jun 2023
Hi guys! What a lovely day I had with you!!! Thank you so much for taking the time to write about your experience and I’ll be looking forward to seeing you again soon.
Ciao
Doug_S, Jun 2023
We booked this tour several weeks before our visit to Tuscany as it seemed like a great fit for our group of 6 including 2 children and others who have expertise with wine looking for a fine wine experience. So the fact that this was advertised as "Flexibility to customize your itinerary to your own preferences" it seemed like we could help shape the itinerary.
However upon contacting the operator, Anna, we were told that it would be planned for us by a sommelier but we could not provide input. With further inquiry we were told these would be high quality wines that were non-commercial (which was explained as not distributing their wine outside of direct to consumer).
The day of the trip we were picked up by a friendly driver named Paola right on time outside our apartment. We then drove about an hour to reach a very small, quaint family owned winery in Chianti. This was a wonderful experience as the host/owner walked us through 4 wines in a rustic and charming setting.
The sights along the drive were outstanding and Paola provided nice details about the Chianti region. During the drive we asked if we would be traveling outside of Chianti to other parts of Tuscany. We did understand that wine meccas like Montepulciano and Montalcino would be a far travel but possibly we'd work our way back from there. Particularly places like San Gimiginano which specialized in whites (one member of our group can only drink white wines) so would have been nice for her. At this point Paola indicated that we had booked a Chianti wine tour, which surprised us. We showed her the printed page from our booking that said Tuscany vs Chianti and she indicated she had perhaps misunderstood. She explained that she was subcontracted theough Ana and basically took it on when bookings were heavy. This does appear to explain the origin of some of the communication issues.
We had lunch at a small restaurant/winery called Sant'Agnese. This one was in a gorgeous setting and food was good, but the host was very focused on marketing their brand and didn't provide much information about the wine or wine making (we even had to ask the vintage!). Nice place, but too heavily commercial.
One of the highlights of the tour was a quick visit to a small hill town called San Donato. What a gem!
The final winery, Montecchio, was much larger and the staff person there was very knowledgeable and provided a brief cellar tour followed by a tasting of 4 wines.
All in all, we had a nice day filled with beautiful sights in the Chianti region and a reliable drive. We also got to have a nice lunch and several tastings. That said, we didn't feel we got precisely what we had booked given we stayed only in the one region (Chianti) and didn't have the ability to provide any input on our day.
If you just want a fun day in Chainti with gorgeous sights and some wine, this is a great tour for you! If you want to do a serious wine tasting of world class wines (which is what we hoped for) it will be a bit disappointing. I only wish we had an opportunity to provide some input on the sort of tour we wanted as I think this could have been a perfect day.
Response from Host, Jun 2023
Dear Doug, thank you so much for taking the time to write the review about your experience.
Although I can totally understand the personal point of view about the single wineries, I can’t really say the same about the overall review which can be very confusing to readers/travelers and sadly what I read is not appropriated in respect of what you booked: the itinerary stated in the description is Chianti and Supertuscan wines which are produced in the mentioned area you covered during your tour, clearly the tour can’t cover Brunello or Nobile wines which are on a completely different location of Tuscany as well as it’s never mentioned in the program of this tour and if you check here as well my company provides also a Brunello tour from Florence (Top Brunello tour) at a very different price due to obvious reasons.
This tour is supposed to cover 3 wineries that you did in order to taste different wines from the area and they’re all very different settings of course and it’s not a customized tour that again our company provides through different means.
In our communication we never mentioned any of these regions/wines and we were never asked about plus what you purchased here it’s a quite clear tour and itinerary so it’s not fair to point we provided something else because it shadows the years of experience and professionalism we based our company which doesn’t provide random experiences suitable for expert wine connoisseurs but also to wine curious.
Bailey_S, May 2023
Tour guide was very nice. Our second winery stop was amazing. The timing seemed off all day. We were picked up at 9:00 the first winery was not ready for us. Then we were two hours too early for our lunch stop. Our guide told us she would show us a small town. Not a lot of direction. Got to see some cute shops. She called to warn the lunch winery we were early and then once we got there we were still too early. Third winery was fine. They definitely didn’t seem ready for us either. The whole thing was a bit awkward and uncomfortable and I think if they would have just started it later than 9 and ended it sooner than 5 it would have been a lot better. We were back to Florence way before 5. There was just a time management issue. If guide could have communicated a bit better more regularly. So that we weren’t left wondering what to do. Maybe even give guests a bit of space to explore on there own. Tour guide was very informative. A great driver. And car was clean. But she was sick with a cold so a mask or maybe a different driver would have been a better choice that day.
Response from Host, May 2023
Dear Bailey, thank you so much for taking the time to write about your experience.
I’m very sorry already from the title of your review!
Everything was set up for the private tour so I’ll be sure to check why you got the feeling that nobody was waiting for you as all the providers were carefully selected as per usual and our standards are always pretty high from the wineries to the guides and definitely we never provide random drivers but high-end driver/guides as you stated she was very informative!
Hopefully next time you’ll be here you’ll contact me personally and I’ll be able to show you around Tuscany or Italy as per our expectations and experience.
Looking forward to seeing you.
Tina_W, Mar 2023
We had a fantastic tour with Anna! With her Sommelier expertise she took us to 3 different wineries in the Chianti region. All 3 offered something different which led to a fantastic day through the countryside. Anna was full of knowledge and energy and made this a really fun day for the whole family. If you want something more specific, I’m sure she could accommodate. Thank you Anna for a well rounded tour! We will remember you when we drink the wines we shipped back to the USA. ❤️
Terrance_W, Mar 2023
Highly recommend Anna and Cool Tours. She made the tour fun and the Tuscan wineries and country side were wonderful.
Response from Host, Mar 2023
Thank you so much for choosing me and for the great day together! Terry the best
Jolene_G, Feb 2023
Incredible experience - highly recommend! I’ve done numerous wine tours through Tuscany and this is by far the best yet!
Adam_A, Feb 2023
Anna was such a fun tour guide! Not only was she extremely knowledgeable about the Chianti region, but also was so fun to have a part of our group for the day! Felt like a friend was showing us around one of her favorite areas. The 3 locations she brought us to were perfect and so enjoyable to walk around and learn how they create their delicious wines. We ate a delicious lunch at our second vineyard and it was the best food I have eaten in Italy! She informed us that that winery does cooking classes so we definitely expect to do that when we return!
Malcolm_G, Sep 2022
Our driver Massimo was wonderful. The winery selection was excellent. A really great day. Highly recommended!
Response from Host, Sep 2022
Thank you, thank you so much for writing about your experience! I’m very very happy you enjoyed the selection of the wineries and my collaborator.
I’m sorry I missed you this time but I hope we’ll have the opportunity to meet in person next time. Ciao Anna
Robert_D, Aug 2022
Best thing we did in Florence / Tuscany. Anna is AMAZING!! She planned the perfect itinerary for my fiancé and I. The 3 vineyards we went to were gorgeous and the staff working were so friendly. We also really wanted to see a medieval Tuscan town, so Anna made time to take us to San Gimignano (also highly recommend). Anna is so personable and friendly + knows so much about wine! I wouldn’t book with anyone else the next time we go back — only Anna.
Truly the best. Do not book with anyone else!!
Meghan_W, Aug 2022
We had an incredible day with Paola! She took us to beautiful wineries that were all very different. The wine, food, and experience at the wineries was exceptional! She was incredibly knowledgeable about the area and wine. One of the best days of our trip. I would highly recommend this private tour!
Ryan_B, Aug 2022
We visited 3 phenomenal wineries with Paola in the Chianti Classico region. They were all unique and had a lot to offer. From amazing wine and food to stunning views, I would definitely recommend! We couldn’t ask for a better guide, Paolo was wonderful and extremely knowledgeable.
Teodora_O, Jul 2022
Anna was ABSOLUTELY AMAZING! This wine tour was a highlight of our time in Italy and probably one of the best things I’ve ever done. Anna is so easygoing and knowledgeable and makes you feel right at home. The wineries she took us to were absolutely gorgeous and allowed us to feel like we were the only people there. This is an absolute must if you’re coming to Tuscany and I would recommend this experience with Anna to anyone!
Response from Host, Jul 2022
Teo and Marco…. Thank you so much for your kindness and the fun we had together!! I’ll be looking forward to seeing you again soon….
Joy_P, May 2022
From the moment we were picked up for the tour, it was special. Frederico was a great and informative host. He took us to 3 delightfully different vineyards but each special in its own way. I know a lot about Napa wines and have visited many vineyards in that region, but I did not know much about the wines in the Tuscany region. I cannot say enough great things about the not only how great the wines are but also the small vineyards whose owners obviously love and believe in what they do and the product shows it. We were in both Florence and Rome for 10 days and we all agreed that this wine tasting tour was our best experience of the trip. We will absolutely return!
Matthew_L, May 2022
While this tour has a lot of wine, I would recommend it to everyone visiting Florence who wants to experience the Tuscan countryside for a day. Our guide Paula was fantastic and knew everyone wherever we went, and took us not only to stellar wineries (that also offered some of the best olive oils and balsamics I’ve ever had), but also carved out some time to explore Castellina. And the lunch was by far one of the best experiences we had in Florence generally. Do this tour!
Response from Host, May 2022
Dear Matthew thank you so much for taking the time to share about your experience with us and I’ll be looking forward to having you back here.
Best Anna
Yvonne_H, Apr 2022
Paola is a wonderful guide. We had 3 great winery experiences. The lunch, paired with wines was superb! The views of the countryside are spectacular. Paola is professional, yet friendly, responsible, tending to every detail and answering every question. We would recommend this tour everyone wanting a special experience. Thank you Paola!!
Response from Host, Apr 2022
Thank you so much for taking the time to write about your experience with us!!! Looking forward to seeing you again
Jordan_F, Apr 2022
This was the most amazing tour. Our guide Paula was INCREDIBLE!! If you get her you are bound to have a perfect day. I wish I could relive this tour over and over again. Had the chance to visit 3 different wineries all bringing a different vibe to the day. 10/10
Response from Host, Apr 2022
Dear Jordan, thank you so much for taking the time to write about your experience with us! It has been a pleasure meeting you when you were with Paola in the wine region and I hope we’ll have the opportunity to meet soon again!
Colleen_L, Mar 2022
Where to begin! This was an amazing experience from pick up to drop off. Paola was our guide for the day and she was beyond exceptional. She took us to 3 beautiful private wineries and had a delicious authentic homemade Italian lunch at one of them. We bought so much wine and oil and made life long memories. The region surrounding Chianti is truly a dream to be immersed in.
Response from Host, Mar 2022
Dear Collen, thank you so much for taking the time to write about your tour and I’m very happy to read this and that you enjoyed the experience! I’ll be looking forward to hosting you again and meeting you!
Rebecca_L, Nov 2021
A group of 5 wine-loving friends from Kentucky:
Paola was our guide and she was exceptional! Knowledgeable, a great sense of humor, and she did not get upset when we lingered over the most fantastic meal we had on our trip. Lunch at Sant Agnese Farm was unbelievable! One of our party was gluten free and they went above & beyond to have fabulous substitutions. The GF pasta was wonderful. We were late to the last winery and Paola called & the tasting staff stayed late for us & we were also able to tour the olive oil press. All in all a really fabulous day!! Strongly recommend to wine lovers! Was more wine drinking than tasting! We shipped wine home - very easy & reasonable.
Ask for Paola - she was fabulous!!
Response from Host, Nov 2021
Hi Rebecca! Thank you so much for taking the time to write this review and I’m happy you enjoyed our tour.
Looking forward to seeing you again!
Taylor_W, Sep 2021
Wonderful visit with a great host. Our guide was great and easy to talk to. The wineries were so friendly and inviting. The tour provides a lot of education on the region and wine making. I'd definitely recommend the tour.
Response from Host, Sep 2021
Dear Taylor thank you so much for taking the time to write about your visit and I’m very happy you enjoyed what we did!!
Looking forward to seeing you soon again.
Sia_H, Aug 2020
This was an absolutely amazing experience - every minute of the entire day. It was my husband and I with our brilliant, fun, super knowledgeable guide Anna. We visited 3 private beautiful wineries, had a super delicious lunch at one of them, met all the lovely owners, bought fantastic wine and learned a bunch about Chianti wines from Anna. We will definitely do it again, can strongly recommend!
mrofe86, Feb 2020
We had so much fun on this tour - it was one of the highlights of our visit to Italy. I love that Anna took us off the beaten path to family-owned wineries. I despise touristy locations, and these wineries were just the opposite of touristy. We visited a few wineries and I enjoyed that we weren't rushed. We got to just sit, relax, and really just take in the experience. We had some great conversations with the winery owners and met so many cute cats and dogs.
Anna is great. I was nervous that something would go wrong because we were just visiting Tuscany for the day and on a strict time schedule, but everything went perfectly. She picked us up from the train station and dropped us off with time to spare.
Oh, and because I wasn't feeling well due to a cold, one of the winery owners gave me a shot of grappa. So much fun.
stevewinawer, Oct 2019
From the moment we got picked up at our apartment through the end of the day was nothing short of awesome. Our guide, Frederico, was so very warm and a perfect blend of facts and funny stories. The vineyards we went to were very beautiful with the lunch on the farm making us want to stay for a nap.
Kelsey_G, Oct 2019
We spent 2 weeks in Italy and this day was by far the highlight of our trip! Our guide was incredibly knowledgeable and kind. The wineries he selected for us were carefully curated and the wine was incredible. Everything about the winery we had lunch at was fabulous, the views, the wine, the food and the company... all spectacular! I would 100% recommend this to anyone who wants to spend a day in the Tuscan country side and experience delicious wine and food!
Response from Host, Oct 2019
Dear Kelsey, thank you so much for your review and nice words about your experience! I work very hard to give my clients the best and give you an authentic experience along with the wines. I hope we’ll be able to host you again soon.
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