Private 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.
Why Tuscany
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 kilometres 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.
The areas
Each part of Tuscany has its own character and its own kind of road. Knowing the difference helps in choosing the right experience.
Chianti Classico
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.
Siena and the Crete
South of Siena the landscape changes abruptly: the woods disappear and bare clay hills take over, shifting colour 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.
Val d'Orcia
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.
Montalcino and Montepulciano
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 centre.
Bolgheri and the coast
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.
Days at the wheel
A single day, morning to evening, driving through the hills. Supercar or classic car.
1 daySiena and the Val d'Orcia by supercar
Val d'Orcia
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1 dayFrom Florence to the Val d'Orcia by supercar
Departing from Florence
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1 dayThe Val d'Orcia by classic car
Val d'Orcia
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1 dayFrom Siena to Monteriggioni by classic car
Chianti and Siena
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1 dayMontalcino and Brunello by supercar
Montalcino
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1 dayMontalcino and Brunello by classic car
Montalcino
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1 dayCastello di Brolio by supercar
Chianti Classico
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1 dayCastello di Brolio by classic car
Chianti Classico
ExploreDays devoted to wine
Wineries, tastings and lunch, with a private driver: nothing to think about at the wheel.
The itineraries
Two or three days to cross Tuscany end to end, with overnight stays and chosen stops.
Browse by kind of experience
If you already know how you want to live it, start here.
When to come
Spring and early autumn are the best windows: the light is soft, temperatures allow driving with the windows down or the roof open, and the landscape is at its peak — green and in flower through April and May, golden and busy with harvest between September and October.
Summer is hot inland, but early mornings and late afternoons remain ideal, and the coast offers an alternative. Winter has less colour but also less traffic: roads are clear, wineries quieter, and the low light over the clay hills is particularly beautiful.
How a private day works
Experiences are private: no groups, no shared departures. The route is agreed in advance and the pace adapts to the guests — a stop can be extended, a stretch of road added, the order of the day changed.
You can choose to drive — supercar or classic car — or to be accompanied by a private driver, which leaves you free to taste and to take in the landscape without a thought. Day experiences run for a full day; multi-day itineraries add overnight stays and changes of scene.
Departures are from Siena or Florence. Each experience has its own page with the route, the duration, what is included and the conditions of participation.
Check availability
Tell us your dates and the kind of experience: we will come back with a tailored proposal.