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Retrace the route of the famous Mille Miglia classic car race through the Tuscan countryside in a unique vintage car experience. Whether self-guided or led by an expert tour leader in a pace car, enjoy a round trip through the sublime landscapes of the Creti Senesi and Val d’Orcia from the luxury of your vintage car. 

The route begins at the medieval village-fortress of Radicofani, with its unparalleled views of the Val d’Orcia, and follows the panoramic Via Cassia (SR2), an ancient Roman road that will take you into the heart of Siena. The drive should take approximately 1 hour 30 minutes each way, leaving you plenty of time to stop off for a bite of lunch and explore the many historical landmarks and natural wonders along the way. If you are staying in one of our luxury villas near Siena, you can view the complete route here. 

Personalise your itinerary in Tuscany

With only three hours of driving to complete your round trip, the Mille Miglia Vintage Car Experience: Tuscany Edition, invites you to relish the beauty of Tuscany at a far more leisurely pace, combining the region’s cultural landmarks with a pitstop or two to sample the exquisite local cuisine. Following the pick-up and briefing on how to use your classic car at 10.00am, how you choose to fill your day can be completely customised to you. 

The Via Cassia from Radicofani to Siena connects pretty villa†ges surrounded by the breathtaking scenery of the Creti Senesi and Val d’Orcia. Stop and unwind in the thermal baths that dominate the central Renaissance piazza at Bagni San Filippo, or opt for something wilder and bathe in the hot natural springs in the woodland outside Bagno Vignoni. Pull over in your vintage convertible to marvel at the Cipressi di San Quirico d’Orcia; you can walk from the Via Cassia to see this surreal ancient ring of cypress trees up close. San Quirico d’Orcia also sits at a neat crossroads between Pienza and Montalcino if you feel like taking a detour to either of these landmark destinations. Head into the centre of Pienza, the city of lovers, for a tranquil spot of lunch or even a pecorino tasting. Or why not venture deeper into the heart of the Montalcino terroir to breathe in the vineyard-clad views and pick up a case of Brunello or two.

Even your start and end destination can be tailor-made to you; why not end your vintage car experience in Siena instead, just in time for dinner and a well-deserved glass of Orcia DOC wine in the famous Campo. Explore Siena Cathedral before dining at Taverna di San Giuseppe for unpretentious Siennese cuisine served up in an ancient Etruscan cellar.  

If this sounds like your dream day out, but your heart is set on another destination in Italy, head to Italy’s Green Heart for the Mille Miglia Vintage Car Experience: Umbria Edition or explore the shores of Lake Garda with the Mille Miglia Vintage Car Experience: Lombardy Edition. Find out more about renting a vintage car in Italy with Sprintage.  

Find your dream vintage car 

Sprintage are classic car enthusiasts and a self-drive rental service offering a select portfolio of iconic vintage cars. Whether you picture yourself winding through cypress groves in a red Duetto Alfa Romeo Spider 1982 or would rather bask in the Tuscan sun in a forest-green Triumph Spitfire 1977 convertible, Sprintage will help match you to your dream vintage car.

Each car seats two people, perfect for a romantic day out. However, you can hire up to 15 cars if you are travelling with a larger group of friends and would like an expert tour leader to guide you in a pace car. Discover the complete portfolio here and then contact our award-winning Concierge to plan your day out winding your way through the breathtaking Val d’Orcia.
 
Schedule details

The experience will start at 10.00am and end at 6.00pm in Radicofani, where you will collect your car and be given a full briefing on how to use it, and drop the car at the end of the day. The route to and from Siena takes approximately 1.5 hours each way, which will allow you plenty of time to enjoy a leisurely drive, stop for lunch and revel in the beauty of the Val d’Orcia. 

  • Max. 2 persons per car (4 persons in VW Beetle)
  • Max. 15 cars per group
  • Available all year round
  • Approx. 3 hours of driving (round trip)
  • Languages: English, Italian
  • All of the cars are manual
  • Transport to and from the pick-up/drop-off point is not included

Included in the price: Car rental from 10.00am to 6.00pm, the cost of petrol/gasoline, car insurance and the price of the pace car with an English-speaking tour guide if you are travelling in a larger group.
 

Experience details
Min 2 persons - Max 2 persons.
  • Available from January to December
  • Approx. 3 hours of driving (round trip)
  • Languages: English, Italian
Included in the price:
Car rental from 10.00am to 6.00pm, the cost of petrol/gasoline, car insurance and the price of the pace car with an English-speaking tour guide if you are travelling in a larger group.
From
€ 550 for 2 people
Or call us on +44 20 7684 8884 to speak with one of our experts
Tour category:
Great outdoors
Price List:
Persons € Euro (*) £ Pounds (*) $ Dollars
2 person € 550 £ 511.5 $ 748
Please Note: Tuscany Now & More act only as an agent in respect of any bookings for experiences which we take and/or make on your behalf. Your booking with us is subject to our Booking Conditions and the specific booking conditions of the Property Owner and you are advised to read both carefully prior to booking.
Note: Transport is not included in the price.
Or call us on +44 20 7684 8884 to speak with one of our experts

More experiences

Need help? Ask our Concierge Service at +44 20 7684 8884 or by e-mail

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