Classic Car Tour Tuscany

The legendary Mille Miglia route opens the rally, then gelato tasted at Gelateria Dondoli, crowned world champion, before an optional second day through the Crete Senesi, where Gladiator was filmed – two nights of classic car rallying through Tuscany.

From£2,868pp

Duration2 days

StyleConvoy

Best suited toClassic car enthusiasts

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An independent Stradora pick. Details from the operator's published information, last checked 28 Oct 2026. Stradora DiscoveryChosen independently by our editors because we think it's worth the drive. We're not partnered with this operator: dates, prices and booking are handled by them, and we last checked their published details on 28 Oct 2026.

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2 nights through Italy

Two nights of classic car rallying through Chianti, with a choice of more than forty vintage cars to drive and the flights from Germany included.

Florence opens it, with a walking tour taking in the Ponte Vecchio, the Uffizi and the Duomo and lunch at the Mercato Centrale, before a transfer out to the garage, a briefing and a first drive into the countryside to San Gimignano.

The rally day follows the Mille Miglia route, the open-road race that ran from Brescia to Rome and back between the wars and still gives its name to the best roads in Italy. Badia a Passignano comes first for coffee, then Greve in Chianti, with Macelleria Falorni, the oldest butcher’s shop in Tuscany, and Badia a Coltibuono for wine and olive oil. San Gimignano closes the day with gelato at Dondoli, whose owner has held the world title. A four-day version adds a second rally day through the Crete Senesi, where Gladiator was filmed, and a night in Siena.

Flights from Germany, the car with a hundred and fifty free kilometres, fuel, technical support and an escort and replacement vehicle, hotel transfers, two or three nights in four-star hotels, the lunches, coffee breaks and dinners on the itinerary, the olive oil tasting, a roadbook and the parking are all included; alcoholic drinks with dinner are not. Three days is a long weekend rather than a tour, and the cars are the product: the choice runs from a Jaguar E-Type to a Porsche 356 Speedster, and swapping between them is half the point. Spring and autumn are the seasons in Tuscany.

Style

Convoy, Guided, Rally

Duration

Weekend (1-3 nights)

Region

Europe

Vehicle provision

Vehicle provided

Group size

Starts/ends

Florence, Italy

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