Private Off Road Wine Tour in Chianti from Florence

Recommended by 100% of travelers

Badge of Excellence

Florence, Italy

7 hours (approx.)
Pickup offered
Group discounts
Mobile ticket
Offered in: English

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Overview

Experience the hidden beauty of Tuscany like never before—aboard a Land Rover Defender, journey through the region’s legendary "strade bianche" (white roads), the secret gravel paths winding through vineyards, olive groves, and deep forests. Your journey includes three winery visits, each offering a unique perspective on Chianti Classico and its appellations. The experience culminates in a traditional Tuscan lunch, where authentic flavors meet world-class wines, creating a true taste of Tuscany.

Land Rover Defender ride through Tuscany’s hidden roads
Visits to three wineries, with tastings at each stop
Traditional Tuscan lunch, paired with local wines
Guided tour of vineyards & cellars

What's Included

Local expert Driver/guide
Lunch

Typical Tuscan lunch
3 Wineries visit + tasting

Meeting and Pickup

You can head directly to the meeting point, or request pickup

Pickup points

Select a pickup point

Meeting point

Piazza della Repubblica, 50123 Firenze FI, Italy

End point

This activity ends back at the meeting point.

Operating hours
.9:00 am

Itinerary

Castellina In Chianti

5 hours • Admission Ticket Free

Additional Info

Confirmation will be received at time of booking
Not wheelchair accessible
Service animals allowed
Infants must sit on laps

Most travelers can participate
Vegetarian option is available, please advise at time of booking if required
This is a private tour/activity. Only your group will participate

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Cancellation Policy

You can cancel up to 24 hours in advance of the experience for a full refund.

Traveler Photos

Gallery picture 1 (from a traveler's review)

Gallery picture 2 (from a traveler's review)

Gallery picture 3 (from a traveler's review)

Gallery picture 4 (from a traveler's review)

Gallery picture 5 (from a traveler's review)

Featured review

Debra_F

Phillipe was wonderful. Extremely knowledgeable and a joy to be with. The wine tasting was perfect and the scenery was amazing! We had a wonderful lunch at an out of the way vineyard with a spectacular view. We would HIGHLY recommend this tour and ask for Phillipe!!

Reviews

5.0

based on 18 reviews

Total reviews and rating from Viator & Tripadvisor

We perform checks on reviews

Great local wineries and a great tour guide

Brent_S, Mar 2026

Our tour guide, Tomasso, was full of information and a great host throughout the day... providing recommendations of local restaurants ans shops, as well as helping us order a couple cases of wine for shipment back to the U.S. Each of the wineries provided a different experience and were increasingly quaint. The second two wineries included tours by the owners (the third owner did not speak english so Tomasso led the tour and tastings) and meeting multiple generations of the families. Tommasso was a gentleman throughout and the more quaint wineries provided a more authentic experience for our family.

Response from Host, Apr 2026

Thank you for your kind review! We’re glad Tommaso made your experience informative and enjoyable, and that you appreciated the unique, authentic charm of the wineries. We hope to welcome you and your family again soon!

The best winery day tour in Tuscany

Sarah_H, Jul 2024

We have taken many winery tours in Napa, Greece, Fredericksburg TX etc. if you’re looking for some adventure with Wineries this is perfect for you! Most places we visited I felt were off the beaten track and we had the wineries mostly to ourselves. The lunch included is a ton of food! This company also offers a service to choose from wine bottles from all the wineries to buy and will ship to you in one shipment. Tomasso (I think I spelled correctly) was our guide and he was so kind and attentive!

Response from Host, Jul 2024

Dear Sarah, thank you for choosing to explore the Chianti wineries with us! We are very happy to read that the tour was appreciated and we are glad that our Tommaso made your day memorable. We hope you can take the memory of this land with you while drinking a glass of Chianti in the comfort of your own home! We will be happy to welcome you again on a future trip to Tuscany. Kindest regards - Tuscany Private Tour

Wine and olive oil

Erin_H, Nov 2023

Trip was fantastic. Our guides were great and shared many great stories. The 3 wineries we went to were amazing. Each very different but all with a great product. We loved trying the fresh olive oils at each as well.

Response from Host, Nov 2023

Buongiorno Erin, Thank you so much for taking the time to write a review, we are so proud to create happy memories for our clients! Hope we will have the opportunity to arrange something else in your favor during your next trip to Tuscany. Best regards

We had an excellent guide...

Stuart_M, Jul 2023

We had an excellent guide and driver. We appreciated being able to order from all of the wineries at the end through the tour company. 10/10 would recommend this tour!

Response from Host, Jul 2023

Buongiorno and thank you for taking the time for this review. We are so pleased to know you enjoyed your tour and we know that our driver guides play an important role in it. Have a lovely day!

Nothing like Wine to make your day

Debra_F, Jun 2023

Response from Host, Jun 2024

Dear Debra, thank you so much for your review. We are really happy to know you have enjoyed your day. We hope to see you soon!!

Best of Tuscany

Matthew_B, Sep 2022

Excellent tour. Could not have asked for anything better. Great wineries, lunch and tour guide… Picked us up in Florence and delivered us back in the evening…. Everything in between was grapes and heaven…

Response from Host, Sep 2022

Buongiorno, thank you so much for choosing our tour and for this great review. We are so proud of making client happy! Hope we will have the possibility to arrange another experience for you in the past.

Amazing - personal - wine tour !!

jgparry, May 2022

We loved our guide Jessica. She made the experience amazing ! We especially loved our home cooked lunch at La Piaggia winery. Great to meet the owners and see them at work. Such a fun day with amazing wines !

Response from Host, Jun 2022

Buongiorno jgparry, thank you so much for this great review. we strongly believe that people are important to make our customers live an authentic Tuscan experience! Hope to see you again soon!

Beautiful Tuscany Wine Tour!

John_K, May 2022

This was a wonderful addition to our trip and a great way to see the country side. We were new to wine tasting, and Leonardo (our guide) walked us step by step through the process. It was fun to see beautiful Tuscany! The winery's we visited felt intimate. It was neat to see the process used to produce the wines. Our lunch was divine on a private family farm. The food was excellent. Would definitely recommend.