With its unmatched views of the Val d'Orcia, the mediaeval village-fortress of Radicofani serves as the starting point for the route. From there, it proceeds along the panoramic Via Cassia (SR2), an old Roman road that will lead you right into the centre of Siena. The drive should take about one and a half hours each way, giving you plenty of time to eat lunch and explore the numerous historical sites and scenic attractions along the way. You can see the entire route if you're staying in one of our opulent villas close to Siena.

Customize your Tuscany travel itinerary

The Mille Miglia Vintage Car Experience: Tuscany Edition invites you to enjoy the beauty of Tuscany at a much slower pace, combining the region's cultural landmarks with a pit stop or two to sample the delectable local cuisine. With only three hours of driving to complete your round trip. After the pick-up and instruction on how to operate your classic car at 10:00 am, how you choose to spend the rest of the day is entirely up to you.

From Radicofani to Siena, the Via Cassia links charming villages encircled by the breathtaking scenery of the Creti Senesi and Val d'Orcia. Stop at Bagni San Filippo's thermal baths, which dominate the main Renaissance piazza there, to relax or go wild and soak in the hot natural springs in the forest nearby Bagno Vignoni. The Cipressi di San Quirico d'Orcia can be seen up close by walking from the Via Cassia; pull over in your vintage convertible to be in awe of them. If you feel like making a side trip to either Pienza or Montalcino, San Quirico d'Orcia is also conveniently located between these two famous cities. Head into Pienza's historic centre for a peaceful lunch spot or even a pecorino tasting. Pienza is known as the "city of lovers." Or, why not travel further into the Montalcino terroir to take in the views covered in vineyards and buy a few cases of Brunello.

Even your start and end points can be customised to your preferences; why not end your vintage car experience in Siena instead, just in time for dinner and a well-earned glass of Orcia DOC wine in the city's famed Campo? Visit the Siena Cathedral before dining at Taverna di San Giuseppe, which serves straightforward Siennese food in a former Etruscan cellar.

If you think this sounds like your ideal day out but have your sights set on another Italian location, consider taking the Mille Miglia Vintage Car Experience: Lombardy Edition or the Mille Miglia Vintage Car Experience: Umbria Edition. Learn more about Sprintage's vintage car rentals in Italy.

Locate your ideal vintage vehicle

Sprintage is a self-drive rental company that specialises in iconic vintage cars and is run by classic car enthusiasts. Sprintage will assist you in finding your ideal vintage vehicle, whether you envision yourself cruising through cypress groves in a red Duetto Alfa Romeo Spider from 1982 or would prefer to soak up the Tuscan sun in a forest-green Triumph Spitfire convertible.

Each vehicle has seating for two people, making it ideal for a date. If you are travelling with a bigger group of friends and would like a knowledgeable tour guide to lead you in a pace car, you can hire up to 15 vehicles. View the entire portfolio here, then get in touch with our distinguished Concierge to schedule your day of exploring the breathtaking Val d'Orcia.

Schedule information

The experience will begin at ten in the morning and end at six in the evening in Radicofani, where you will pick up your car, receive a thorough orientation on how to operate it, and return the car at the conclusion of the day. The drive to and from Siena takes about 1.5 hours each way, giving you plenty of time to take it easy, eat lunch, and take in the splendour of the Val d'Orcia.

Maximum 2 people per car (4 persons in VW Beetle)

15 cars most per group

accessible all year long

3 hours or so of driving (round trip)

Italian and English both

The vehicles are all manual.

No transportation is provided to and from the pick-up/drop-off location.

The cost of the pace car with an English-speaking tour guide if you are travelling in a larger group, as well as the cost of gas/oil, car insurance, and car rental from 10:00 am to 6:00 pm, are all included in the price.