Private Tuscany tours
No groups, no shared departures, no imposed schedule. This is how our days are built and how to pick the format that suits you.
Rocca d'Italia runs private tours in Tuscany departing from Siena or Florence: no groups, a route agreed in advance and changeable on the day, in three formats — at the wheel of a supercar, at the wheel of a classic car, or with a private chauffeur. Driving days are built around one car, which means two people; with a chauffeur the number rises to the group traveling together.
What private means here
Private does not only mean there are no strangers along. It means the route is decided with you beforehand and can change while it happens: a stop runs long because the winery deserves it, a stretch of road gets added because the light is right, the order of the day flips because the rain stopped. None of that is possible with a group, which is why we do not run them.
The second consequence is numbers. Driving days are built around one car, which means two people; with a driver the number rises to the group traveling together. We never put separate clients in the same car to fill it.
The third is who is on the other end. One person follows the day from start to finish, from the handover briefing to the lunch stop — not a call center, but someone reachable who knows where you are and what you booked.
The three formats
The difference is not the route. It is who drives, and whether the day turns around the road or around what sits along it.
At the wheel of a supercar
The day is built on the driving: scenic roads chosen for how they drive, stops timed so they do not break the rhythm. This is the format for people who take their pleasure behind the wheel and want the landscape to move at that speed.
At the wheel of a classic car
Same territory, opposite pace. A historic car imposes slowness, windows down and longer stops: the halts become half the day rather than a pause in it. It is also the format that copes best with the narrow lanes of Chianti.
With a private chauffeur
Nobody drives, and that changes two things: you can drink at the tastings, and you look out of the window instead of at the road. It is the obvious choice when the day is built around wineries, and the comfortable one when the group is larger than two.
One day or several
A single day is enough for one area: the Sienese hills and the Val d'Orcia, or Chianti as far as a castle, with pick-up and drop-off at the same point. It is the format for travelers who have a few days in Tuscany and would rather not move their luggage.
With two or three days the nature of the trip changes: you cross the region instead of radiating out from one base, you sleep along the route and you reach what a single day cannot — from Chianti to the Bolgheri coast, or from Chianti to Montalcino by way of Siena. If none of the existing formats matches what you have in mind, the day gets drawn from scratch.
Private days in Tuscany
Every Tuscan experience, from the single day to the three-day itinerary.
3 days3 Days in a Supercar · Siena Duomo & Tastings
The most complete journey: three days between Siena, the Val d'Orcia and Chianti at the wheel of a supercar, with exclusive access to Siena's Duomo and tastings at the most prestigious wineries.
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3 days3 Days in a Classic Car · Siena Duomo & Tastings
The same complete three-day itinerary, lived at the wheel of a classic car: Siena, the Val d'Orcia and Chianti, with exclusive access to Siena's Duomo and tastings.
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3 days3 Days with Private Chauffeur · Siena Duomo & Tastings
The full three-day journey with a dedicated private driver: Siena, the Val d'Orcia and Chianti in total comfort, with exclusive access to Siena's Duomo and tastings.
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1 daySiena & Val d'Orcia Supercar Tour
A one-day supercar tour through the Val d'Orcia and the Sienese hills, with lunch in central Siena and a guided visit to the city and its Duomo.
Explore1 daySupercar Tour from Florence · Siena & Val d'Orcia
Departure from Florence with pick-up at the address you choose: Chianti, Siena and the Val d'Orcia in a single day of driving.
Explore1 dayVal d'Orcia & Montalcino Classic Car Tour
A one-day classic car tour from Siena: lunch in Sovicille, the roads of the Val d'Orcia, Montalcino and a return via Rapolano Terme.
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1 daySiena to Monteriggioni by Classic Car
A day in a classic car from the gates of Siena to the walls of Monteriggioni, with a stop in the village and lunch included.
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7 hoursMontalcino & Brunello Supercar Tour
Seven hours by supercar from Siena: lunch in Sovicille, a guided Brunello tasting at Casanova di Neri and a return via Rapolano Terme.
Explore7 hoursMontalcino & Brunello Classic Car Tour
Seven hours by classic car from Siena: lunch in Sovicille, a tasting at Casanova di Neri and a scenic return via Asciano.
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7 hoursCastello di Brolio · Supercar
An afternoon and evening in Chianti: tasting and castle tour at Castello di Brolio and dinner in Castellina in Chianti.
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7 hoursCastello di Brolio · Classic Car
An afternoon and evening in Chianti by classic car: tasting and castle tour at Castello di Brolio and dinner in Castellina.
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8 hoursChianti Classico Wine Tour · Private Chauffeur
Two Chianti Classico wineries in one day, with a private chauffeur, pick-up in Siena and Tuscan lunch included. Price per person.
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8 hoursBrunello Wine Tour in Montalcino · Private Chauffeur
Two Brunello wineries in the Montalcino area, with a private chauffeur, pick-up in Siena and Tuscan lunch included. Price per person.
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8 hoursMontepulciano Wine Tour · Private Chauffeur
Two wineries in the Montepulciano area, with a private chauffeur, pick-up in Siena and a typical Tuscan lunch included. Price per person.
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2 daysFrom Chianti to Bolgheri in a Supercar
Two days from Chianti to the Bolgheri coast at the wheel of a supercar, among vineyards and signature wineries.
Explore2 daysFrom Chianti to Bolgheri in a Classic Car
Two days from Chianti to the Bolgheri coast at the wheel of a classic car, among vineyards and signature wineries.
Explore2 daysFrom Chianti to Bolgheri with Private Chauffeur
Two days from Chianti to the Bolgheri coast with a dedicated private chauffeur: freedom to taste, to take in the landscape and to arrive in style.
ExploreWhere you start from
The pick-up point changes what fits into a day. Each city has its own page.
The questions we're asked most
Who can drive in the classic car and supercar formats?
The requirements apply only to whoever drives: at least 21 years old, a license held for at least 2 years and a credit card in their name for the pre-authorization of the deductible. There is no age limit for the other passengers, and none of this applies to the private chauffeur format.
Do I need a driving license or a credit card for a deposit?
No. The experience is with a private chauffeur: no driving requirements apply and there is no deductible to pre-authorize.
What time does the experience start?
You choose a departure time between 9:00 and 11:00, agreed with the program for the day.
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.
This experience is part of the private days and itineraries we organize across Tuscany.
Tuscany experiencesLet's build your day
Tell us your dates, the number of guests and the kind of day you have in mind.