
Private Off Road Wine Tour in Chianti
Traveler rating
5.0/5
Based on 23 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Private Off Road Wine Tour in Chianti worth booking?
Private Off Road Wine Tour in Chianti is a 6-hour experience in Siena, Italy, from $380 per person. It scores 71 out of 100 on the Outty Ranking, which we label “Strongly Recommended”, based on a 5/5 rating across 23 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 71 / 100
- Rating
- 5/5 (23)
- Duration
- 6 hours
- From
- $380 per person
Discover the highlights of Chianti Classico while riding through Tuscany’s backroads in a Land Rover Defender. There is a special kind of magic in driving along Tuscany’s hidden gravel roads, le strade bianche, as we call them—beautiful shortcuts winding through vineyards, olive groves, and deep woods, offering breathtaking views. Along these routes, we will visit three different wineries, from small family-owned estates to major producers of the area. In the second winery, guests will also enjoy a light lunch paired with selected wines. We will explore not only the natural beauty of the region but also some of the most prestigious wines in Tuscany: Chianti Classico and all its appellations, learning the secrets of production from the vines to the glass. The meeting point is at our office in Castellina in Chianti.
What you get
About this experience
Discover the highlights of Chianti Classico while riding through Tuscany’s backroads in a Land Rover Defender. There is a special kind of magic in driving along Tuscany’s hidden gravel roads, le strade bianche, as we call them—beautiful shortcuts winding through vineyards, olive groves, and deep woods, offering breathtaking views. Along these routes, we will visit three different wineries, from small family-owned estates to major producers of the area. In the second winery, guests will also enjoy a light lunch paired with selected wines. We will explore not only the natural beauty of the region but also some of the most prestigious wines in Tuscany: Chianti Classico and all its appellations, learning the secrets of production from the vines to the glass. The meeting point is at our office in Castellina in Chianti.
What's included
Included
- Wine tasting
- Lunch
- Driver-guide
What you'll see and do
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.
30 minutes here
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.
60 minutes here · Admission included
Where it starts and ends
Meeting point
Siena
We have a free parking space
Hotel pickup
No pickup: everyone meets at the start point.
Ends at
We have a free parking space
Before you book
- Cancellation
- For a full refund, cancel at least 24 hours before the scheduled departure time.
- Languages
- en, it, es
- Ticket
- Mobile Only
- Runs on
- Every day
- Group size
- Up to 8 travelers per booking
- Operated by
- Tuscany Private Tour
Know before you go
- 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
Photos






What travelers are saying
Outty’s summary of the themes that recur across 23 traveler reviews. Written by us, not quoted from reviewers.
The guide
7 mentionsTravelers single out the guide as the reason the experience works.
Knowledge and storytelling
7 mentionsReviewers describe the commentary as informative rather than scripted.
Food and drink
7 mentionsThe tastings and food stops are a highlight for most reviewers.
Photo opportunities
3 mentionsThe views and photo stops come up again and again.
Good for families
2 mentionsReviewers traveling with kids report it landed well with their group.
Traveler reviews
23 verified traveler reviews for Private Off Road Wine Tour in Chianti. Ratings and reviews provided by Viator and Tripadvisor.
Bellissima Toscana
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!
Response from the operator: Buongiorno and thank you so much for your kind email. We are so happy to know you enjoyed your day with Gabriele and well know he's a great driver guide. We hope to see you soon in Tuscany again.
via Viator
Fantastic Adventure with an Excellent Guide!
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 ⭐️⭐️⭐️
Response from the operator: Buongiorno from Tuscany, thank you so much for this great review! We well know that guides are an important part of the experience and that Chiara is great. We are looking forward to having you with us again soon for another experience.
via Tripadvisor
Perfect day!
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!
Response from the operator: Buongiorno and thank you so much for taking the time for this great review, we are so happy to create memorable days and we know Chiara gives a great contribution to that! We hope to see you soon again in Tuscany.
via Tripadvisor
Off Road Wine Tour
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!
Response from the operator: Dear Lauren, we are very happy to read that you enjoyed the experience and the guide Chiara who was with you during the tour . We look forward to welcoming you again on future holidays in Tuscany! Kindest regards The Team
via Tripadvisor
Great time driving through the Italian countryside
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!
Response from the operator: Buongiorno, thank you so much for this great review. We are so happy to know you enjoyed our experience and well know that Gabriele is a great driver guide. We hope to arrange another service for you in the future, best regards.
via Tripadvisor
Good to know
- Duration
- 6 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Every day
- Hotel pickup
- No pickup, meet at start point
- Booked in 30 days
- 8
- Verdict
- Strongly Recommended
Who runs this experience
Operated by Tuscany Private Tour, who run 22 experiences we rank across 3 cities, with an average Outty Ranking of 51.2.
See everything Tuscany Private Tour runsWhy this scores 71
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Private Off Road Wine Tour in Chianti: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Siena.
How much does Private Off Road Wine Tour in Chianti cost?
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Prices start at $380 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Siena usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.
How long does Private Off Road Wine Tour in Chianti take?
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Plan for about 6 hours from start to finish, not counting travel to the meeting point. Most travelers leave another 30 minutes on either side so the rest of the day in Siena is not rushed.
Is Private Off Road Wine Tour in Chianti worth it?
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It holds an Outty Ranking of 71 out of 100, which we label "Strongly Recommended". That score blends traveler sentiment (5/5 across 23 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable last minute in Siena, and how flexible the cancellation terms are.
Can I cancel or reschedule Private Off Road Wine Tour in Chianti?
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Yes. Cancel free up to 24 hours before the start time for a full refund. Inside that window the booking is non-refundable, and no-shows are not refunded.
Is Private Off Road Wine Tour in Chianti suitable for kids and families?
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Yes, all ages are welcome. Families should still weigh the 6-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book Private Off Road Wine Tour in Chianti?
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Around 8 people booked this in the last 30 days, so popular slots go early. Two to three weeks ahead is comfortable in shoulder season, while summer weekends and holidays in Siena can sell out a month out. Same-day spots do open up when other travelers cancel, so it is worth checking if you are already in town.
What should I bring or wear?
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Bring photo ID, your booking confirmation on your phone, a refillable water bottle and comfortable shoes. Dress for the weather in Siena and add a light layer if any part of the 6-hour experience runs outdoors or after sunset.
Where does Private Off Road Wine Tour in Chianti start and how do I get there?
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The exact meeting point and directions are on your voucher once you book, and they sit in central Siena within reach of public transport. Arrive 15 minutes early: late arrivals are treated as no-shows by most operators.
What are the best things to do in Siena?
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On Outty we rank every Siena experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena, Siena: A Wine Tour and Tasting Experience, Small-Group Montepulciano and Pienza Day Trip from Siena. The city page groups everything into most popular, highest reviewed, last minute and family-friendly so you can build a day around what actually delivers.
When is the best time to visit Siena?
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Booking patterns follow the same curve: prices and queues climb in peak weeks, while shoulder season gives you better availability on the top-ranked experiences and more room to change plans.
How many days do you need in Siena?
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Three full days covers the headline sights without sprinting. A workable rhythm is one anchor experience each morning, such as this one, an unhurried afternoon in a single neighborhood, then a food or nightlife booking in the evening. Five days lets you add a day trip outside the city.
Do I book through Outty or through the operator?
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Outty ranks and explains the experiences, then hands you to Viator to complete the booking with the operator directly. The price is the same as booking on Viator yourself, and Outty earns an affiliate commission on the referral, which is how the rankings stay free to read.
What is included in Private Off Road Wine Tour in Chianti?
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Included: Wine tasting; Lunch; and Driver-guide. Always check the voucher for the final list before you travel.
Where is the meeting point for Private Off Road Wine Tour in Chianti?
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We have a free parking space Hotel pickup is not included, so plan your own transport and arrive 15 minutes early.
What languages is Private Off Road Wine Tour in Chianti offered in?
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It is offered in English, Italian and Spanish. Pick your language when choosing a date and time, as not every departure runs in every language.
Will I get instant confirmation and a mobile ticket for Private Off Road Wine Tour in Chianti?
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Confirmation is sent by the operator after booking, usually within 48 hours; if it is not confirmed you are not charged. Mobile tickets are accepted, so you can show the voucher on your phone.
Is Private Off Road Wine Tour in Chianti wheelchair or stroller accessible?
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The operator notes: Specialized infant seats are available. If accessibility is critical, contact the operator after booking to confirm arrangements for your date.
What happens to Private Off Road Wine Tour in Chianti if the weather is bad?
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This experience depends on good weather. If it is canceled because of poor weather, you are offered a different date or a full refund.
What do travelers say about Private Off Road Wine Tour in Chianti?
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Across 23 reviews averaging 5.0 out of 5, recurring themes include the guide, knowledge and storytelling, food and drink. Travelers single out the guide as the reason the experience works.
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