Classic Car, Wine Tasting & Castello di Brolio Experience
A curated journey through the Chianti hills aboard a timeless automobile
This classic car Chianti wine tasting experience invites guests to explore the Tuscan countryside at a deliberate, unhurried pace, combining the nostalgia of vintage motoring with the cultural depth of Chianti wine heritage. Departing from Siena, the route winds through vineyard-lined hills toward one of Tuscany's most storied estates. The full day closes with a convivial dinner inside a historic castello.
The experience is structured around three distinct pleasures: the aesthetic and sensory pleasure of driving a classic car through panoramic Tuscan roads, the cultural pleasure of visiting Castello di Brolio and participating in a guided wine tasting, and the convivial pleasure of a Tuscan dinner at Castello di San Leonino. Each element connects to reinforce a coherent vision of what Chianti represents as a territory.
Rocca d'Italia coordinates all logistics, from the welcome at Villa Ermellina to the final dinner arrangements, so guests can focus entirely on the landscape, the wine and the road. The itinerary also passes by Castello di Spaltenna and through Castellina in Chianti, adding further layers of historical context to the journey.
The package is designed for intimate travel, accommodating one or two guests per classic car. Whether travelling as a couple or solo, the private format ensures a personalised experience calibrated to the pace and preferences of those aboard.
Experience Highlights
Travel through the Chianti countryside aboard a curated classic car, following scenic routes designed for driving pleasure and panoramic views.
Participate in a guided wine tasting at Castello di Brolio, one of Tuscany's most iconic wine estates and the historic home of Chianti Classico.
Tour the grounds and architecture of Castello di Brolio, combining cultural discovery with the pleasure of Chianti wine.
The itinerary includes a scenic passage by Castello di Spaltenna and continues through the celebrated Castellina in Chianti area.
The day concludes with dinner at Castello di San Leonino, offering a refined and convivial Tuscan setting to close the experience.
Rocca d'Italia staff accompany and coordinate the full itinerary, providing private assistance from the welcome briefing to the final destination.
The route departs from Villa Ermellina in Siena and traverses the heart of the Chianti Classico zone, connecting heritage landmarks through countryside roads.
Itinerary Overview
Guests are received by the Rocca d'Italia team at Villa Ermellina. A short operational briefing covers the route, driving sequence, timing and coordination rules before departure.
The classic car departs from Siena and follows a curated itinerary through the Chianti countryside. The opening driving section introduces the landscape through vineyard roads, rolling hills and the first views of historic estates.
Guests arrive at Castello di Brolio for a guided wine tasting and a visit to the castle. The tasting format and wines served are subject to availability and final confirmation by the estate.
After the tasting, the classic car continues through the Chianti area, passing by Castello di Spaltenna before arriving in Castellina in Chianti. This stage bridges the cultural afternoon with the evening program.
The experience concludes with dinner at Castello di San Leonino in Castellina in Chianti. This final moment offers guests a refined Tuscan setting after the full day of driving, tasting and discovery.
What Is Included
Included
- Private classic car for 1 or 2 guests
- Welcome and operational briefing at Villa Ermellina
- Curated driving route through Chianti countryside
- Wine tasting at Castello di Brolio
- Guided tour of Castello di Brolio
- Scenic passage by Castello di Spaltenna
- Dinner at Castello di San Leonino
- Rocca d'Italia staff coordination throughout
Not Included
- Fuel for the classic car
- Return transport after dinner (unless arranged separately)
- Personal expenses and gratuities
- Any items not explicitly listed as included
Important Information
Reserve Your Classic Car Experience
This private Chianti itinerary is available for one or two guests per classic car. Spaces are limited and the package price remains fixed regardless of group size.
Book Now
