
Private tours and exclusive experiences in Tuscany
From the Chianti hills to the Val d'Orcia, from Siena to Montalcino and down to the Bolgheri coast: private days and itineraries, at the wheel or with a driver.
- Private days, never shared
- Drive yourself or be driven
- A proposal within 48 hours
Why Tuscany
Rocca d'Italia runs private days and itineraries in Tuscany departing from Siena or Florence: at the wheel of a supercar or a classic car, or with a private chauffeur. They range from a single day to two- and three-day itineraries across Chianti, Siena, the Val d'Orcia, Montalcino and the Bolgheri coast.
Some places are crossed, others are driven. Tuscany belongs firmly to the second kind: a region of ridgelines, of bends that follow the shape of the hills, of cypress rows that frame the road like stage wings. It is no accident that some of Europe's most photographed roads are here, nor that the Mille Miglia still crosses the region every year. The landscape is not a backdrop — it is the reason for the journey.
What sets Tuscany apart from other scenic destinations is density. Within a few dozen kilometers you move from the woods of Chianti to the bare clay hills around Siena, from fortified hilltop villages to the ordered vineyards of Brunello, and on to the cypresses that run down to the sea at Bolgheri. The landscape can change completely in half an hour of driving, without a single anonymous stretch. That concentration is rare, and it explains why a single day can be enough for a complete experience.
Then there is everything else: a cuisine that changes from valley to valley, wineries that open their doors to those who arrive accompanied, castles and abbeys punctuating the route, art cities that sit half an hour from the country roads. Tuscany lets you build a day in which driving, wine, landscape and history are not separate activities but one continuous story.
Tuscany in seven details




Days we design here
Private days at the wheel of a supercar or a classic car, or with a private chauffeur.
about 7 hoursThe Roads of Val d'Orcia
Siena · San Quirico d'Orcia · Pienza · Bagno Vignoni · Siena
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about 7 hoursHeart of Chianti
Siena, Firenze o hotel · Castello di Brolio · Gaiole e Radda in Chianti · Castellina in Chianti · rientro
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about 7 hoursThe Brunello Road
Siena · Montalcino · Casanova di Neri · le strade di Sant'Antimo · Siena
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about 7 hoursDolce Vita in Chianti
Siena, Firenze o hotel · Castello di Brolio · le strade del Chianti · Radda in Chianti · Castellina in Chianti · rientro
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about 7 hoursDolce Vita in Val d'Orcia
Siena · San Quirico d'Orcia · Pienza · Bagno Vignoni · Siena
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about 7 hoursMedieval Tuscany
Siena · Monteriggioni · Val d'Elsa · San Gimignano · Siena
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7 daysTuscan Islands
Arcipelago toscano
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about 7 hoursBrolio Castle & Chianti Classico
Siena, Firenze o hotel · Castello di Brolio · rientro
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about 7 hoursBrunello at Casanova di Neri
Siena · Casanova di Neri · Montalcino · Siena
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about 7 hoursTwo Estates of Chianti Classico
Siena, Firenze o hotel · Castello di Brolio · Castello di Radda · rientro
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about 7 hoursTwo Faces of Brunello
Siena · Col di Lamo · Casanova di Neri · Siena
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about 7 hoursBoscarelli & Vino Nobile
Siena · Boscarelli · Montepulciano · Siena
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about 7 hoursPetra & Bolgheri
Siena, Firenze o hotel · Petra · Bolgheri · rientro
ExploreThe areas
Each part of Tuscany has its own character and its own kind of road. Knowing the difference helps in choosing the right experience.

The land between Florence and Siena: the most wooded and the most drivable. Narrow roads climbing and falling through vineyards, continuous bends, almost no straights. This is the area of historic castles and the oldest wineries. For pure driving pleasure, this is the best ground.
South of Siena the landscape changes abruptly: the woods disappear and bare clay hills take over, shifting color with the seasons. Roads become wide and sweeping, with very long views. Siena, with its square and cathedral, remains the urban anchor of the whole area.
A UNESCO site, and the postcard everyone has in mind: cypress avenues, isolated farmhouses on the ridges, villages such as Pienza and San Quirico. It is the most photographed corner of Tuscany, and the one where slowing down pays off — every bend opens a different view.
Two hills, two great wines. Montalcino means Brunello: ordered vineyards, cellars cut into the rock, a fortified village overlooking the valley. Montepulciano, slightly to the east, means Nobile: a vertical Renaissance town with historic cellars beneath the palaces of its center.
Heading towards the sea the landscape opens up. Bolgheri is known for the cypress avenue leading to the village and for the wines that changed the course of Italian winemaking. It is the area that lets a Tuscan itinerary close with sea air.
One team, from first idea to the road
Private, never shared
Every day is built for one group. No strangers, no fixed departures.
One local team
We live between Siena and the Val d'Orcia, and we answer the phone.
Driven before it's offered
We drive each route ourselves before offering it to anyone.
Getting here, and what to know before you book
Which airport should I fly into for Tuscany?
Florence (FLR) is the closest, about an hour from the Chianti hills and from Siena, and is reached with one connection through a European hub. Pisa (PSA) is a similar distance from the coast. If you would rather fly nonstop from the United States, Rome Fiumicino (FCO) is roughly three hours away by road and Milan Malpensa (MXP) around three and a half.
How far in advance should I book?
Late spring and early fall are the busiest windows, and the cars and the wineries for a given date are finite. As soon as your travel dates are firm, write to us: the team replies within one hour, Monday to Friday, so you will know quickly whether the day you want is open.
Do I need an International Driving Permit?
Italy asks drivers holding a non-EU license to carry an International Driving Permit alongside it. In the United States you get one from AAA, usually the same day, and it is valid for a year. Bring both documents on the day, together with a passport and a credit card in the driver's name.
Where do the Tuscan days start, and how do I get there?
Departures are from Siena or Florence; the Siena days meet at Villa Ermellina, Via Custoza. Most guests base themselves in Florence, in Siena or at a hotel in the countryside — tell us where you are staying when you book and we will agree the meeting arrangements from there.
What time is it in Tuscany, and when will I hear back?
Italy runs on Central European Time: six hours ahead of New York, nine ahead of Los Angeles. A message written in the American morning arrives inside the Italian working day, so you will normally have an answer before your afternoon.
Will the day be in English?
The language of the day — guide and driver — is agreed when you book. Tell us what you would like and we will confirm it in the proposal, before anything is paid.
How do I pay, and what happens if my plans change?
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. Every quote is in euro and is prepared for your request.
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Your Tuscany, built around you
Send us dates and ideas: a tailored proposal within 48 hours.