Private Chianti Wine Tour from Florence: Discover Breathtaking Views and World-Famous Wine

This personal tour will aid you in exploring and appreciating the quintessence of an area filled with stunning sights, undulating hills, and quaint towns, that for ages has been providing a globally renowned and loved product: the Chianti wine!

Duration: 8 hours
Cancellation: 24 hours
Highlights

Meet our driver at your hotel to begin your journey to the stunning Tuscan countryside. We’ll travel along quaint country roads to reach Montefioralle, a charming Medieval village perched on a hill. We’ll take a brief stop for a short walk before heading downhill to Greve in Chianti, a delightful town known as the capital of Chianti wine.
Our driver will…

What's Included
  • Hotel pickup and drop-off
  • Exclusive private tour experience
  • Personalized attention from driver/guide
  • Luxurious travel in a Mercedes Vclass minivan
  • All fuel surcharges included
What's Not Included
  • Lunch
  • Gratuities
  • Wine tasting fees
Location
Montefioralle
Località Castello di Montefioralle
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
4.9
(21 Ratings)
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1 star
Lilduster
Oct 10, 2025
A nice way to see the Chianti area - We were met by Alex (our driver/guide). Alex was friendly and knowledgeable . He actually lived in the same city that we are from for a few years. We had and enjoyable day with a pleasant drive and a wine tasting, lunch and another wine tasting ( later in the day). We visited Castellina and San Gimignano. A relaxed and enjoyable day. Alex made the trip even more enjoyable.
Review provided by Tripadvisor
S4044udbrendak
Sep 29, 2025
Magnificent Day in Chianti with Massimo - If you love wine and want to learn about the Chianti region, we highly recommend booking a private guided tour with Massimo - it will be the highlight of your time in Italy. Massimo‘s knowledge of the Italian wine regions is vast and his enthusiasm is infectious. He took us to several charming small towns we would have never otherwise known about. But best of all, Massimo introduced us to two very special small family wineries that were fabulous. Each winery presented their wonderful wines with a food pairing that was exquisitely prepared and perfectly complimented each wine. Massimo took the time to get to know us and then tailored the day perfectly to suit our specific interests. Throughout the day, Massimo also provided ample free time for us to explore both the towns and the winery experiences on our own. Although Massimo was our guide, by the end of the day it felt like he was an old friend we’d known for years. We can’t recommend Massimo highly enough!
Review provided by Tripadvisor
Lauren_k
Sep 25, 2025
We had a great time with... - We had a great time with our tour guide. We really enjoyed the family owned vineyard that we stopped into!
Review provided by Viator
Joseph_b
Sep 20, 2025
Wine time - Massimo is a wonderful tour guide. Very accommodating The stops were all fantastic. I highly recommend this trip
Review provided by Viator
Luigi_d
Jun 18, 2025
Ultimate Experience - This is the ultimate way to experience Tuscany and the Chianti region. From the mid-evil towns to the endless rolling hills and it terrific vineyards, we had an amazing and memorable experience. Our tour guide Alex was knowledgeable and informative. His understanding of the history and geography along with his command of the English language, for an Italian native, were impressive. Of the two vineyards we visited Corbucci was by far our favorite. The owner Francisco was a spectacular host not only sharing his wine but the story behind each vintage. The flavors were wonderful and our time there is something we won’t soon forget. Especially since we’ll have several bottles to enjoy when we get back home.
Review provided by Viator
Erica_b
Mar 20, 2025
Massimo was an excellent... - Massimo was an excellent tour guide!! He tailored our experience to what we wanted , found nice wineries for us to visit, and took us to some neat small towns. He shared lots of information about the area and culture, and answered lots of our questions. He gave us great local restaurant recommendations. He even returned a lost item from the van the next day!! Highly recommend!
Review provided by Viator
W4644pmcharlesm
Jul 25, 2024
Booked this tour after Wonderful experience at Bocelli concert the day before with the same guide - Good afternoon Max, I wanted to send this note of thanks while our experience was still fresh in our mind. Your service starts and ends with your drivers. Our driver, Massimo, made our time here in Florence unforgettable! His promptness, personality, knowledge of the area, as well as English, were unsurpassed. He was so helpful and patient with us, which put me at ease. Not everyone can walk at a quick pace but he was so understanding and comforting that we enjoyed our time even more. He was very punctual and accommodating since the concert didn’t end till almost 1:00 am. By the time the lines let out, it was nearly 2:30 when we were back at the hotel. I asked we delay the scheduled pick up for later and he was more than happy to oblige. Chianti tour was great! Again, very interesting facts about the region as well as the winemaking too. We’ve been to your fair city before but, this past two days make the previous visits pale in comparison. Thanks for your service and if we are in the area in the future, you will handle our logistics. Sincerely, Charles and Toni
Review provided by Tripadvisor
Aprilww4590pi
Dec 7, 2023
Great day trip from Florence! - We did a day trip from Florence and we had such a great time!! Our guide, Massimo was one of a kind. He absolutely made our trip. He is extremely knowledgeable about all topics, gave us history notes, restaurant and attraction recommendations and was extremely personable! We were tired out from planning our trip so it was very nice to be able to just get into the car and let them take us on their planned route. We drove through Tuscany, stopped for pictures along the way, went to San Gimignano, stopped in a small village, had lunch at a winery, and made a stop in Greve as well. This was a very fun and relaxing day I would highly recommend it.
Review provided by Tripadvisor
Nancynj2016
Oct 21, 2023
wine tour and transfer - Max helped us arrange a wine tour and transfer from Florence to Montepulciano. Sonny, our driver, was professional, delightful and very informative. The wine tour and lunch pairing is not to be missed.
Review provided by Tripadvisor
Hollycp2870uy
Feb 24, 2024
Outstanding guide and tour! - Massimo was an outstanding guide. He was friendly, knowledgeable, and very attentive to our needs and flexible to our desires. We absolutely loved our family winery tour—he could not have chosen better winery for our wine tour experience. Would highly recommend him to anyone looking for a personal tour experience.
Review provided by Tripadvisor
From $115
up to 8 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).