
Private classic car tours in Tuscany and on Lake Como
Back roads, historic houses and cars from another era, with our assistance along the whole route.
Five itineraries in a classic car
Five private experiences at the wheel of a historic car: from the Tuscan hills between Chianti, Siena and the Val d'Orcia to the Bolgheri coast, and on to the villas of Lake Como, plus two single days departing from Siena. Every itinerary is private and built around your dates, your group and your pace, with Rocca d'Italia assistance throughout.

Tuscany Hills · Classic Car
Three days between Chianti, Siena, the Val d'Orcia and Montalcino at the wheel of a classic car.
3 daysfrom €4,980 per car, up to 2 peopleScopri
From Chianti to Bolgheri · Classic Car
Two days from the Chianti hills to the Bolgheri coast, with stops dedicated to wine.
2 daysfrom €3,320 per car, up to 2 peopleScopri
The Villas of Lake Como · Classic Car
A day along the lake shores, among liberty villas, historic houses and panoramic roads.
1 dayfrom €1,900 per car, up to 2 peopleScopri
Val d'Orcia & Montalcino · Classic Car
A day from Siena: lunch in Sovicille, the roads of the Val d'Orcia, Montalcino and a return via Rapolano Terme.
1 dayfrom €1,118 per car, up to 2 peopleScopri
Siena to Monteriggioni · Classic Car
From the gates of Siena to the walls of Monteriggioni, with a stop in the village and lunch included.
1 dayfrom €1,040 per car, up to 2 peopleScopriWhat changes at the wheel
Anyone who has never driven a classic expects a slow car. What they find is a car that asks to be driven, which is an entirely different matter.
Steering and brakes
Little or no power steering: at a standstill the wheel is heavy, in motion it becomes as precise and communicative as no modern car is. The brakes want anticipation — you brake earlier and for longer. These are the two things you get used to in the first few kilometres, and the reason the day always starts with a briefing.
The gearbox
Shifts to be coaxed, not forced: you wait for the synchro, you guide the lever. Some cars want a double-declutch on downshifts. More than anything else, it is the gesture that tells you that you are driving something mechanical, not a computer on four wheels.
Speed
You go slowly, and that is not a limitation — it is the point. At sixty kilometres an hour, windows down and an engine you can hear, you look at the landscape instead of crossing it. The Chianti roads a supercar covers in an hour take a classic a whole morning — and they are better remembered.
The effect it has
In a Tuscan village a supercar turns heads; a classic car brings people out of the bars. It matters more than it sounds: it changes how you are received at the stops, in the squares, at the winery gates.
What a day in a classic car looks like
It starts with the handover and a longer briefing than usual: controls, gearbox, brakes, the quirks of the particular car. In a classic that is not a formality — the first kilometres are taken calmly, and the team stays available if anything feels wrong.
Then you set off, on a route agreed beforehand but adaptable: extend a stretch you enjoy, stop where the view deserves it. Couples take turns at the wheel. The itineraries are built on back roads, which is where these cars make sense.
The stops — lunch, a tasting, a castle or a winery — are not a side dish: they are half the day. A classic car imposes a slower rhythm, and the programme is built to go with it rather than fight it.
Classic car or supercar?
The classic is for those who want to feel the mechanics and are in no hurry. It asks for attention, gives back character, and turns even a short transfer into something worth recounting. It is also the better choice for the narrow streets of the villages, where a wide car is a problem.
The supercar is the opposite: immediate, powerful, easy to drive well from the first kilometre. Choose it to concentrate on the landscape and the pleasure of driving without thinking about technique, or to try a model you do not have at home.
Those who would rather not drive at all can do the same itineraries with a private driver: the role changes, the route does not. It is the right format when the day involves several tastings.
The questions we're asked most
Who can drive?
The requirements apply only to whoever drives: at least 21 years old, a driving licence held for at least 2 years, and a credit card in the driver's name for the pre-authorisation of the deductible. There is no age limit for the other passengers.
How does the deductible work?
The deductible is €10,000 for every model and is held as a pre-authorisation on the driver's credit card. It is not a charge: the amount is released at the end of the experience if there is no damage. Third-party liability and collision (Kasko) cover are included.
How many kilometres are included?
150 km per car are included. Additional kilometres are charged at €5.00/km.
What should I bring?
A valid driving licence for each guest who will drive, an identity document or passport, the credit card in the driver's name and comfortable shoes suitable for driving.
Is the price per person or per car?
The price is per car, for up to 2 people.
How do I pay, and what happens if I need to cancel?
Payment is 100% on booking confirmation. You get a full refund up to 30 days before the date; with less than 30 days' notice the fee is non-refundable.
How quickly will I get a reply?
The team replies within one hour, Monday to Friday.
Would you rather drive a supercar?
Private supercar toursLet's build your classic car itinerary
Tell us your destination, dates and number of guests: we prepare the programme and check which cars are available.

