Classic Cars

Classic Car, Wine Tasting & Castello di Brolio Experience

A private afternoon and evening classic car experience through the Chianti countryside, combining scenic driving, Tuscan heritage, wine tasting and refined hospitality. The experience starts from Villa Ermellina in Siena with departure at 14:00, followed

← All experiences

Duration~7h
DestinationToscana
Guests10
LanguagesEN, IT
DifficultyEASY

This private classic car experience is designed for guests who wish to discover Chianti through a slower, more elegant and nostalgic way of travelling.

The day begins at Villa Ermellina in Siena, where guests are welcomed by the Rocca d’Italia staff before receiving a short operational briefing. At 14:00, guests depart aboard the selected classic car and begin a curated route through the Tuscan countryside toward the Chianti area.

The first key stop is Castello di Brolio, where guests take part in a wine tasting at 15:00 and enjoy a tour of the castle. This is the central wine and cultural moment of the experience, combining the atmosphere of one of Tuscany’s most iconic estates with the pleasure of discovering the Chianti wine territory.

After the tasting and castle tour, the itinerary continues through the Chianti countryside, passing by Castello di Spaltennaand continuing toward Castellina in Chianti. The experience continues with dinner at Castello di San Leonino, selected as the final hospitality moment of the day. guests then return at Villa Ermellina, where the experience ends.

The package is valid for one classic car and 1 or 2 guests. The package price remains the same whether one or two guests participate.

Itinerary

— Welcome at Villa Ermellina, Siena
Guests are welcomed by Rocca d’Italia staff at Villa Ermellina in Siena.
This first moment introduces the atmosphere of the day: private hospitality, curated logistics and a route designed around Tuscany’s landscape and wine culture.
📍 Villa Ermellina Siena, a Tribute Portfolio Hotel, Via Custoza, Siena, Province of Siena, Italy
— Operational briefing
Before departure, guests receive a short operational briefing.
The Rocca d’Italia team presents the itinerary, timing, driving sequence, basic safety indications and coordination rules for the tour.
📍 Villa Ermellina Siena, a Tribute Portfolio Hotel, Via Custoza, Siena, Province of Siena, Italy
— 14:00 | Departure by classic car
At 14:00, guests depart from Villa Ermellina aboard the selected classic car.
The route begins from Siena and continues toward the Chianti countryside, following a curated itinerary designed to combine driving pleasure, panoramic roads and timeless Tuscan scenery.
📍 Gaiole in Chianti, Province of Siena, Italy
— Scenic drive toward Castello di Brolio
The first driving section leads guests toward Castello di Brolio.
This part of the route introduces the Chianti landscape through countryside roads, vineyards, hills and historic estates, creating the ideal setting for a classic car experience.
📍 Castello di Brolio, Località Madonna a Brolio, Gaiole in Chianti, Province of Siena, Italy
— 15:00 | Wine tasting and tour at Castello di Brolio
At 15:00, guests arrive at Castello di Brolio for the wine tasting and castle tour.
The experience includes a guided tasting and a visit to the castle, subject to final confirmation by the estate. The exact tasting format, wines served and duration may vary depending on availability and operational conditions.
📍 Castello di Brolio, Località Madonna a Brolio, Gaiole in Chianti, Province of Siena, Italy
— Chianti Classic Car Tour via Castello di Spaltenna
After the wine tasting and castle tour, the experience continues with a scenic classic car route through the Chianti area.
The itinerary passes by Castello di Spaltenna, adding another historic landmark to the journey and reinforcing the identity of the experience as a true Chianti heritage tour.
📍 Castello di Spaltenna, Via Spaltenna, Gaiole in Chianti, Province of Siena, Italy
— Arrival in Castellina in Chianti
The route continues toward Castellina in Chianti, one of the most representative areas of the Chianti territory.
This stage marks the transition from the driving and wine experience to the evening part of the program.
📍 Castellina in Chianti, Province of Siena, Italy
— Dinner at Castello di San Leonino
The experience concludes with dinner at Castello di San Leonino, in Castellina in Chianti.
Dinner is designed as the final convivial moment of the day, offering guests a refined Tuscan setting after the classic car tour, wine tasting and Chianti itinerary.
📍 San Leonino, Province of Siena, Italy
— End of the experience at Villa Ermellina
After dinner, the experience ends at Villa Ermellina or with return logistics arranged separately, depending on the selected package.
Rocca d’Italia staff coordinate the itinerary and provide assistance throughout the experience.
📍 Villa Ermellina Siena, a Tribute Portfolio Hotel, Via Custoza, Siena, Province of Siena, Italy

Included

Classic car Rental
Fuel costs.
Welcome by Rocca d’Italia staff at Villa Ermellina in Siena.
Operational briefing before departure.
Curated classic car itinerary from Siena through the Chianti countryside.
Route planning and on-site coordination by Rocca d’Italia staff throughout the experience.
Wine tasting at Castello di Brolio, subject to estate availability and final confirmation.
Tour of Castello di Brolio, subject to estate availability and final confirmation.
Scenic route passing by Castello di Spaltenna.
Dinner at Castello di San Leonino in Castellina in Chianti, according to the agreed menu.
Parking fees during the planned itinerary.
Package valid for one classic car and 1 or 2 guests.

Not included

Deposit for car insurance
Any extra food, drinks, wine pairings, à la carte orders or special requests not included in the agreed dinner menu.
Any additional wine, bottles or products purchased at Castello di Brolio or during the experience.
Tasting upgrades, private cellar visits, premium wine selections or additional estate services unless expressly confirmed in the selected package.
Hotel pick-up and drop-off, private transfers or chauffeur services to and from Villa Ermellina or Castello di San Leonino, unless arranged separately.
Personal expenses, tips, fines, damage excess, security deposit, additional insurance and any service not specifically listed as included.

Know before you go

Important information before booking: Departure from Villa Ermellina is scheduled at 14:00. Guests are kindly asked to arrive in advance for the welcome and operational briefing. The wine tasting and castle tour at Castello di Brolio are scheduled at 15:00. The final tasting format, wines served, tour details and duration are subject to confirmation by the estate. This experience follows a planned Chianti driving itinerary passing through Castello di Brolio, Castello di Spaltenna and Castellina in Chianti. Minor route or timing adjustments may be necessary due to traffic, weather conditions, road closures, estate availability, restaurant availability or operational needs. Guests who drive must hold a valid driving licence and comply with the rental provider’s requirements, including any age limits, security deposit, insurance conditions and damage excess policies. Drivers are responsible for complying with Italian road-safety rules and alcohol limits. Guests who are driving may choose to taste without consuming, consume responsibly, or participate as passengers where appropriate. Comfortable clothing and shoes suitable for both driving and walking during the castle visit are recommended.

What to bring

Valid driving licence for each guest who will drive. Passport or ID card. Credit card for any rental-provider requirements, security deposit or insurance conditions, if applicable. Comfortable shoes suitable for driving and walking. Seasonal clothing suitable for an afternoon and evening experience. Sunglasses are recommended. A light jacket is recommended for the evening. Any personal medication or essential personal items needed during the experience.