Private Off-Road Wine Tour in Chianti: Land Rover & 3 Wineries

Drive unpaved roads through vineyards instead of sitting in a tour bus on pavement.

A private six-hour wine tour through Chianti Classico on unpaved gravel roads (le strade bianche) in a Land Rover Defender, with stops at three wineries ranging from small family estates to major producers. You taste wines at each stop, enjoy a light lunch paired with selections at the second winery, and explore the region's production methods with a driver-guide who knows the hidden routes.

Step-by-step itinerary

Off-road wine tour in Chianti

• Meet at office in Castellina
• Get Land Rover Defender
• Drive on unpaved roads
• Visit first winery
• Visit second winery with light lunch
• Visit third winery
• Taste 3 glasses of wine at historical winery
• Tour Castellina village with guide

The experience

Six hours on Chianti's gravel backroads (le strade bianche, the white roads locals call them) means you skip the main highways and wind instead through vineyards, olive groves and deep woods in a Land Rover Defender. The vehicle handles terrain a regular car cannot, and the unpaved route itself is the point: these shortcuts reveal the landscape most visitors miss. You start at the operator's office in Castellina in Chianti, where the Land Rover and your driver-guide are waiting.

Three wineries break up the day. The first two are stops for tastings. At the second, a light lunch arrives paired with selected wines. The third winery sits in Castellina's town center, where you taste three glasses and walk through the village with your guide. Between stops, the road itself carries the experience: the gravel surface, the views opening up as you climb and descend, the sense of moving through working countryside rather than past it. The operator works with both small family-owned estates and larger Chianti Classico producers, so the scale and style shift as the day unfolds.

Your guide speaks English, Spanish or Italian and explains how the wines move from vine to glass, grounding the tastings in the region's production methods. Vegetarian options are available if you note them when booking. The tour suits all fitness levels. If you're traveling with an infant, specialized seats are available.

What’s included

• Wine tasting at three wineries.
• light lunch with wine pairing at the second stop.
• three-glass tasting and village walk in Castellina.
• driver-guide for the full six hours.
• Land Rover Defender vehicle and all driving.

Before you book

Days and timesEvery dayDeparts at 10:00

Book up to2d before

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

GroupPrivate

Live guideEnglish, Spanish and Italian

Meeting point and pickupNo hotel pickup: you go to the meeting point. Ends back at the starting point.

Cancellation and refundsFree cancellation up to 24 h before the start. After that, no refund.It may be canceled due to bad weather. If that happens, you're offered another date or a refund.

Prices and times updated 2 days ago

Good to know

Low physical effortInfant seats availablePets welcome

Operated by Tuscany Private Tour

Is this one for you?Pick this tour if you don't have a car or prefer not to drive Chianti's gravel roads yourself: the Land Rover and driver handle the navigation and the terrain, leaving you free to watch the landscape and focus on the wines.

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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 happens if it rains?

It may be canceled due to bad weather. If that happens, you're offered another date or a refund. Free cancellation up to 24 h before the start.

What are le strade bianche and why does this tour use them?

Le strade bianche are unpaved gravel roads winding through the Tuscan countryside. This tour follows them because they pass through vineyards, olive groves and woods, offering views and access to wineries that main roads bypass. A Land Rover Defender is built to handle the terrain, so the backroads become part of the experience rather than a limitation.

How many wineries do you visit and what happens at each one?

You stop at three wineries across the six hours. At the first two, you taste wines. At the second winery, a light lunch arrives paired with selected wines. The third winery is in Castellina's town center, where you taste three glasses and walk through the village with your guide.

What wines will I taste on this tour?

The tour focuses on Chianti Classico and its appellations. The wineries range from small family-owned estates to major producers of the region, so the wines and production scales vary across the stops. Your guide explains the secrets of production from the vines to the glass.

Is lunch included, and are there vegetarian options?

A light lunch paired with selected wines is included at the second winery. Vegetarian options are available. Note your dietary needs in the Special Requirements box when you book.