
Private Off Road Wine Tour in Chianti
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September 2026
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Who is going?
Adults
Age 13 and over
Children
Age 12 and under
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Free cancellation up to 24 hours before. Same price on Viator, Outty earns a commission.
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 $167 per person. It scores 74 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
- 74 / 100
- Rating
- 5/5 (23)
- Duration
- 6 hours
- From
- $167 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 cal
What you get
- Wine tasting
- Lunch
- Driver-guide
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






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
- Price range
- $167 to $333
- Hotel pickup
- No pickup, meet at start point
- Booked in 30 days
- 8
- Verdict
- Strongly Recommended
Why this scores 74
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 $167 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 74 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, Skip the Line: Siena Duomo and City Walking Tour, Siena: A Wine Tour and Tasting Experience. 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.
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