Classic car tours in Tuscany
Private days at the wheel of a vintage car, on the roads of Chianti, the Val d'Orcia and the Val d'Elsa. You drive.
Find inspiration in our signature experiences, or create a journey entirely your own, shaped around your passions and preferences.
How a classic car day in Tuscany works
A classic car tour in Tuscany with Rocca d'Italia is a private day at the wheel of a vintage car, for your group only. You drive. There are three routes: Chianti, leaving from Florence, Siena or your hotel; the Val d'Orcia, from Siena; and Monteriggioni and San Gimignano, from Siena. Each day runs about seven hours.
Tuscany has the roads for an old car: the Chiantigiana between Florence and Siena, climbing through woods and vineyards; the open curves of the Val d'Orcia south of Siena; the road from Siena through the Val d'Elsa to the towers of San Gimignano. A vintage car keeps you at the right speed for them, and every village on the way is a reason to stop.
Each of our days follows one of these routes. The route and the stops are planned before you arrive, the car is ready at the departure point, and you take the wheel. The car is chosen with you based on availability for your date, and the model is confirmed in the proposal.
To drive you need your valid license. If it was issued outside the European Union, you also need an International Driving Permit, carried with your license; in the United States it is issued by AAA and AATA. Apply before you leave home.
Every day is private: nobody joins your group, and the pace is yours. Tell us your dates, where you are staying and how many of you will drive, and the proposal with the estimate arrives within about 48 hours. If you would rather drive a modern supercar, the same regions have supercar days too.
Days we design here
Private days at the wheel of a supercar or a classic car, or with a private chauffeur.
Dolce Vita in Chianti
Siena, Florence or your hotel · Castello di Brolio · the roads of Chianti · Radda in Chianti · Castellina in Chianti · return
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Dolce Vita in Val d'Orcia
Siena · San Quirico d'Orcia · Pienza · Bagno Vignoni · Siena
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Medieval Tuscany
Siena · Monteriggioni · Val d'Elsa · San Gimignano · Siena
ExploreThree routes at the wheel
Three routes, each a full day of driving. Here is what each one covers, and where it leaves from.
Wooded hills, vineyards and stone villages between Florence and Siena. The Dolce Vita in Chianti day stops at Castello di Brolio, the Ricasoli estate near Gaiole, then follows the Chianti roads to Radda and Castellina. It leaves from Florence, Siena or your hotel. You are driving, so the wine tastings belong to a separate chauffeured day.
The open valley south of Siena, on the UNESCO World Heritage List since 2004, with cypress rows and long curves. The Dolce Vita in Val d'Orcia day drives from Siena to San Quirico d'Orcia, Pienza and Bagno Vignoni, where the main square is a thermal pool. A stop at the thermal pools of Posta Marcucci can be added.
The medieval side of Tuscany. The Medieval Tuscany day leaves Siena for the walled village of Monteriggioni, crosses the Val d'Elsa and ends among the towers of San Gimignano, with lunch on the way, before the drive back to Siena.
The departure points. The Chianti day leaves from Florence, Siena or your hotel; the Val d'Orcia and San Gimignano days leave from Siena. We do not run departures from Rome: if you are based elsewhere, ask us for a tailor-made plan.
Questions about classic car tours in Tuscany
Can I drive a classic car in Tuscany myself?
Yes. On all three of our classic car days you are the driver. You need your valid license, and if it was issued outside the EU, an International Driving Permit as well.
Do I need an International Driving Permit to drive in Italy?
If your license was issued outside the European Union, yes: Italy asks you to carry an International Driving Permit together with your license. In the United States it is issued by AAA and AATA. Get it before you travel.
Is this a vintage car rental in Tuscany?
It is more than a rental. Instead of collecting a car and finding your own way, you get a private day on a planned route: the car ready at the departure point, the stops arranged, the day built around your group.
Which classic car will I drive?
The car is chosen with you based on availability for your date. We confirm the model in the proposal rather than promising one in advance.
Which classic car tour should I choose?
From Florence, Chianti: the day leaves from the city, from Siena or from your hotel. For wide landscapes and Pienza, the Val d'Orcia. For walled villages and towers, Monteriggioni and San Gimignano. The last two leave from Siena.
Can I combine a classic car tour with wine tasting?
Not on the same day at the wheel: you are driving. Wine tastings are separate days with a private chauffeur, in Chianti, Montalcino, Montepulciano and Bolgheri, and the two fit well on consecutive days.
Can I do a classic car tour in Tuscany from Rome?
Our days start in Florence, Siena or your hotel in Tuscany, not in Rome. If you are based in Rome, write to us and we will plan around where you are staying.
How much does a classic car tour in Tuscany cost?
It depends on the date, the route, the car and the number of guests, so we do not publish a fixed price. Send a request and the proposal with the estimate arrives within about 48 hours.
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Your Tuscany, built around you
Send us dates and ideas: a tailored proposal within 48 hours.