Mille Miglia 2020

4 Day Tour

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Departure dates on request


Experience the Mille Miglia 2020 in a legendary Alfa Romeo classic car

On this trip, you gain a first-hand and hands-on impression of automotive history. The legendary Mille Miglia 2020 involves several hundred participating vintage cars, and it gets the hills of Tuscany trembling as it passes. You are there with them, stylishly seated at the wheel of an Alfa Romeo Spider built in the 1950s.

Mille Miglia – the most beautiful race in the world

Day 1 Drive through a famous wine-growing district
At lunch in the hotel you meet your fellow travelers and the tour staff. We then introduce you to the Nostalgic classic car fleet and explain the roadbook. The first stage leads over lonely country roads so that you get used to »your« Alfa Romeo. In the early evening, you visit a former abbey where wine has been made since the Middle Ages. Dinner at leisure.

Day 2 Crete Senesi
This impressive stage leads, partly on the old Roman road Via Cassia, southwesterly to Siena past Val d’Orcia. Most of today’s itinerary is identical to the legendary Italian automobile race »Mille Miglia«. At lunch you will have the choice of a country inn in old papal town Pienza. The highlight of the afternoon is the Crete Senesi: steep loamy slopes which resemble the moon and a lonesome road running along the ridge. After wine tasting, dinner will be served on the terrace of the hotel.

Day 3 Mille Miglia comes to town
With Nostalgic, you are once again ‘up close and personal’ when the Mille Miglia cohorts drive across Tuscany. More than 400 vintage cars from the earliest days of automotive construction and up to build year 1957, the last construction year that must have participated in the Mille Miglia, are able to take part in this vintage rally. As in the original Mille Miglia, the participants drive on country roads that have not been cordoned off and pass through medieval villages and little towns. You have the opportunity of experiencing a drive through a place like this and of driving along part of the route, stylishly in your Alfa Romeo Spider, in the main body of the event. No other vehicle manufacturer in the world was able to win the Mille Miglia as often as Alfa Romeo. After an interesting day’s driving we serve dinner in a nearby village.

Day 4 San Gimignano
With its impressive medieval skyline, San Gimignano is located high up on the bucket list. The winding, old country road Siena-Firenze leads you from Castellina to Poggibonsi, from there over little driven secondary roads to San Gimignano. The small town is located in the upper Elsa Valley and is rich in art and culture, it is world famous because of the high number of its remaining noble family towers and because of its almost unchanged medieval appearance. The majestic, sleek towers characterize the town silhouette, nicknaming it “medieval Manhattan”. In 1990, the historic old town has been declared World Cultural Heritage by the UNESCO. After the visit, there will be time for an individual lunch break, before heading to the last stage towards the citadel of Monteriggioni. Nearby you will be leaving “your” Alfa Romeos, we will accompany you back to Florence airport or to the hotel if you have arrived by car.

* sharing a double room/ sharing a car
If you would like to book as a single guest, please don’t hesitate to contact us.


All of our itineraries are tailor-made according to your interests and the above itinerary is an example only. Please contact one of our specialists, for your own tailor-made holiday.

Included in your holiday:

  • Transfer from/ to Florence Airport (FLR) to the hotel, as well as on location
  • Nostalgic Alfa Romeo for you to self-drive including fully comprehensive insurance (Euro 500 deductible), fuel
  • 3 nights accommodation incl. breakfast in 4-star Hotel “Borgo di Véscine” at Radda in Chianti
  • 1 lunches, 2 dinners, 1 wine tasting
  • Admission fees, guided sightseeing according to itinerary
  • English-speaking guide and service team during the complete trip
  • Road book
  • Welcome gift

Not included in the arrangement:

  • travel to Florence (FLR)
  • meals unless otherwise indicated

Self drive holiday of Tuscany

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