Private Off-Road Wine Tour Chianti from Siena: 4WD & tastings

The gravel roads of Chianti wind through vineyards most visitors never see.

A private off-road wine tour from Siena takes you through Chianti Classico's hidden gravel roads, called le strade bianche, in a vintage 4WD with a local wine expert. You visit three wineries for tastings and cellars, then finish with a traditional Tuscan lunch in an authentic setting. The route runs six hours and includes hotel pickup and return.

Step-by-step itinerary

Chianti wine tour and tastings

• Meet wine expert guide
• Ride vintage 4WD through Chianti
• Visit three Chianti Classico wineries
• Enjoy traditional Tuscan lunch

The experience

The 4WD leaves your Siena hotel and heads into the backroads that cut through vineyards, olive groves, and deep woods: the kind of terrain a regular car cannot reach. Your wine expert guide drives while narrating the landscape and the region's history. The gravel roads themselves are part of the experience: they slow the pace and open sightlines that the main routes miss entirely.

Three wineries anchor the day, ranging from historic estates to small family-run operations. At each one, you explore the vineyards and cellars with the guide, taste their wines, and learn how Chianti Classico is made. The tastings are not rushed. The guide shapes the stops around the wineries' rhythms and your questions. A vegetarian option is available if you request it when you book.

Lunch arrives in an authentic Tuscan setting, not a restaurant built for tourists, but a place where the food and the stories belong to the region. The meal anchors the flavors and the atmosphere you have been moving through all morning. The tour wraps by early evening when the 4WD returns you to your hotel.

What’s included

• Local expert driver and wine guide.
• visits to three Chianti Classico wineries with tastings at each.
• traditional Tuscan lunch in an authentic setting.
• hotel pickup and return to your Siena accommodation.
• vegetarian meal option available upon request.

Before you book

Days and timesEvery dayDeparts at 09:30

Book up to1d before

AgesAdult (12 and older) · Child (3 to 11 years) · Infant (under 3): free

GroupPrivate

Live guideEnglish, Spanish and Italian

Meeting point and pickupHotel pickup is optional; you can also go straight to the meeting point. Ends back at the starting point.You can choose from 20 pickup points.

Cancellation and refundsFree cancellation up to 24 h before the start. After that, no refund.

Prices and times updated 2 days ago

Good to know

Low physical effortPets welcomeInfants must sit on laps

Operated by Tuscany Private Tour

Is this one for you?Book this tour if you want to reach the small family-run wineries and hidden gravel roads that organized groups cannot access. The private 4WD and expert guide make the backroads safe and navigable, and the six-hour pace leaves room to linger at each winery without feeling rushed through the day.

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Top questions

What languages is the tour guided in?

Live guide in English, Spanish and Italian.

Can children come?

Yes. Ticket types: Child (3 to 11 years); Infant (under 3): free.

What does a Chianti Classico winery visit actually include?

Each winery visit includes access to the vineyards and cellars with your guide, who explains the production process and the estate's history. You taste their wines at each stop. The guide selects which ones based on the winery and your interests.

Can I do this tour if I don't drink wine?

Yes. You travel the same route and visit the same three wineries. You can skip the tastings or ask the guide to explain the wines without tasting them. The lunch and the landscape are the core of the day either way.

Why does the tour use a 4WD instead of a regular car?

The le strade bianche, the gravel backroads, are unpaved and often narrow. A 4WD handles them safely and comfortably, and it is the only way to reach the smaller, more remote wineries that sit off the main roads.

How much time do you spend at each winery?

The guide shapes the time at each stop based on the winery's schedule and your pace. There is no fixed duration. The goal is to explore the cellars and taste without rushing, so stops typically run 60 to 90 minutes depending on the estate.

Is the lunch included in the price, or is it extra?

Lunch is included. It is a traditional Tuscan meal served in an authentic setting as part of the tour. You do not pay separately for it.