Private Tour
Available languages
6 hours
Mobile ticket
Discover Chianti Classico highlights riding through Tuscany’s backroads with Land Rover Defender.
There is a sort of magic on riding through hidden gravel roads of Tuscany, “le strade bianche” that’s how we call them. Shortcuts of rare beauty across vineyards, olive groves and deep woods that offer breathtaking views.
We will have access this way to local wineries, from small family businesses to huge realities of our wine market.
We will discover not only the natural beauty of the area but also some of the most prestigious wines of Tuscany:
Chianti Classico and all its appellations, learning all the secrets of the production, from the vines to the glass.
Wine Cellars may change depending on availability.
Service animals allowed
Specialized infant seats are available
Suitable for all physical fitness levels
Vegetarian options are available; make a note in the 'Special Requirements' box when you book
For a full refund, cancel at least 24 hours before the scheduled departure time.
Wine tasting
Lunch
Driver-guide
Tuscany Private Tour
This is our starting point where we get the Land Rover and start our ride on unpaved road. We will stop into 3 wineries along the way and have several wine tasting, food and winery visits.
La Castellina
This historical winery is located in the town center of Castellina, taste 3 glass of wine and tour the village with you guide.
23 reviews
Total reviews and rating from Viator & Tripadvisor
CharleneC E,
Apr 24, 2025
- Review from Viator
We had a great day with Gabriel, who was very knowledgeable about wine himself and spoke English well, so we didn’t miss out on anything. The three wineries we visited were all lovely and varied in size and philosophy. The wineries were truly off the beaten track and would have been a challenge to find on our own making the day a true adventure. Our group of 6 loved the whole experience …. the wine, the food, the people, and the beautiful scenery. We all would highly recommend this tour!
evanf767,
Oct 29, 2024
- Review from Tripadvisor
What a fantastic and fun day off-roading to the vineyards! It was an entirely new and interesting way to explore the Tuscan landscape and we had such a good time with Chiara. She was an excellent driver and guide, educating us not only on the finer points of the amazing wines we tasted, but on the history of the region, Italian cinema, classic rock, and the nature of feisty vineyard cats. Highly recommend this experience, especially if Chiara’s your guide ⭐️⭐️⭐️

ryankN8794HM,
Sep 4, 2024
- Review from Tripadvisor
Amazing day touring 3 beautiful wineries! Our guide Chiara was friendly, knowledgeable, and great company throughout the day. Lunch was delicious as well. Very memorable day!
laurengY1329KM,
May 5, 2024
- Review from Tripadvisor
My husband and I had the best time on the Off Road Wine Tour! Tuscany Private Tours arranged three different tastings from small family vineyard to larger winery. Our guide, Chiara, was great company throughout the trip and was extremely knowledgable about the area and local wines. She went above and beyond to make sure we had a spectacular trip, and offered to take stops along the way for pictures. This was definitely the highlight of our Italy trip! Thank you, Chiara!




905kaitlint,
Sep 27, 2023
- Review from Tripadvisor
We have nothing but great things to say about our off road wine tour with Gabriel! It was great to drive around the country side in a 70s era Defender while our guide filled us in on the rich history of the area. All wineries/farms we visted were top notch in both service and quality of wine, food, honey etc. Highly recommend this activity!
Cpersad91,
Mar 19, 2023
- Review from Tripadvisor
Fillipo was an amazing tour guide he went out of his way to make us feel comfortable. We highly recommend that you book him for any of your future tours in Tuscany.
Zytra80,
Nov 6, 2022
- Review from Tripadvisor
The Guide was excellent, Filippo, the tour of the best, have good tours in the different wineries
Rosangela G,
Nov 4, 2022
- Review from Tripadvisor
Two fantastic days accompanied by the talented, very nice and very prepared Giada I plan to return and participate in other tours always accompanied by tuscany private tours Simply TOP
Lucyfoote55,
Oct 31, 2022
- Review from Tripadvisor
This was the highlight of our trip! Filippo was fantastic, he speaks incredible english and had every thing planned out perfectly. Would 10/10 recommend this amazing tour 🤩



99carlya,
Sep 25, 2022
- Review from Tripadvisor
We just finished an off road Tuscan wine tour from Castellina with Gabriele and it was a highlight of our three week trip! He took us through beautiful wine country with stunning views of vineyards and olive orchards. We visited three wineries which served delicious wine in amazing settings. Gabriele was very knowledgeable in answering all of our questions- Outstanding tour in every way- a MUST DO! We had a fantastic authentic lunch served at a small vineyard - with home made Tiramisu dessert to top it off!
Operated by Tuscany Private Tour