Tuscany and the “Mille Miglia”

Experience the Mille Miglia 2021 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.

Tuscany and the “Mille Miglia”

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5 out of 5 based on 14 customer ratings
(14 customer reviews)


Per person in double room *
  • 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.


    At a glance: All dates and destinations in our new free brochure.

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  • 14 reviews for Tuscany and the “Mille Miglia”

    1. 5 out of 5


      Mille Miglia – A Great Experience

      Our « Mille Miglia » experience with the team of Nostalic was a great moment. The organisation of our travel, hotel, visits and the superb vintage cars was just perfect. Driving those beauty’s around the Toscana roads, especially in the middle of the legendary race make our hearts beat faster. The group composed of diversified origins (Australia, US, Germany, Switzerland, Italy, Belgium and Luxembourg) was a great fun generator as well. The smiles of the faces after the drives and the emotional good byes the last day are the evidences of success!
      Thanks to the crew, Hotel personnel and last but not least the co-participants.

      Claude & Chris Bettendorf-Degueldre

    2. 5 out of 5


      I liked to ride in the Alfa Romeo Giulia 1600 Spider Veloce and the Alfa Romeo 2000 Spider Veloce, really great!

    3. 5 out of 5


      Very satisfied! I can imagine booking more Nostalgic tours, for example Sicily, South Tyrol, Umbria or Venets.

    4. 5 out of 5


      Perfectly organized event, professional style and best Nostalgic team!

    5. 5 out of 5


      Spent 4 fantastic days in Tuscany. High Fun factor!
      – wonderful street selection
      – beautiful cars (with minor issues but that’s the big attraction!)
      – great locations (hotel, visited cities and restaurants)

    6. 5 out of 5


      It was a wonderful, well organized tour. Thank you very much!

    7. 5 out of 5


      Beautiful streets, great old Alfas, good organization, wines and delicious food… what more could I ask for?

    8. 5 out of 5



    9. 5 out of 5


      Very ingenious tour, perfect organization, nice fellow travellers and dream cars!

    10. 5 out of 5


      Beautiful tour in a dream car, great Tuscan landscape and roads, great organization.
      Absolute recommendation!

    11. 5 out of 5


      Dear Nostalgic Team,

      immediately after returning from our very impressive tour through Tuscany to the Mille Miglia in Siena, I would like to congratulate you not only on your great business idea but also on choosing the initerary, the hotel complex and, above all, your outstanding staff.

      Our entire stay was planned logistically down to the smallest detail, every unexpected challenge was mastered calmly, objectively and competently by the supervising team, and this with a group of 40 partcipants!

      Greatest praise therefore to your team leader Ludwig and his “assistants” Conni and Michael, who could not only give us a perfect travel experience, but also made it possible for me in my special case (acute knee complaints) to save my stay choosing an Alfa “tailormade” for me.

      I would therefore like to ask you to pass on my thanks to your team.

      Best regards, Dr. R. Stanek

    12. 5 out of 5


      It was an unforgettable adventure and we will always keep it in mind!

    13. 5 out of 5


      Dear Nostalgic Team,

      arrived back home, my husband and I would like to take the opportunity to thank you very much once again.

      A great team that we got to know. During this wonderful Mille Miglia trip 2018 they were always with us, extremely committed.

      We were pleasently surprised by the visits at Badia a Coltibuono, Pienza and San Gimignano. We liked it very much.

      We are looking forward to a next voyage of discovery, why not in Bavaria! 😉 In any case we will recommend Nostalgic.

    14. 5 out of 5


      I got the perfect gift from my son, many thanks to him and to Nostalgic.

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  • Additional Information

    Reiseziele nach Oldtimer

    Alfa Romeo Tours




    13/05/21 – 16/05/21

  • Arrangement includes

    • 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


  • Region


    Tuscany is one of the most picturesque regions of Italy. It impresses with its unique and diverse landscape. Vineyards mingle with olive trees and alternate with the original bareness of the countryside. This sparseness is broken up by lanes of towering cypress trees. Little-used roads wind their way up hills and run through small sleepy villages. Like a backdrop from a 1950’s Italian film.

    With Nostalgic you drive on selected routes in Tuscany. Many of them were also sections of the legendary Mille Miglia race. But Tuscany does not only make the hearts of car enthusiasts beat faster. It also offers lovers of culture cities such as Siena and San Gimignano and places of interest such as the fortress at Monteriggioni. Even in the weeks before the world-famous horse race, the Palio, in Siena, you might be able to watch the teams during their rehearsals and preparations for the big race. They stroll through the city in their period costumes and practice on their drums preparing for the perfect entry to the Piazza del Campo.

    Close your eyes and imagine gliding along the dream roads of Tuscany in a classic Alfa Romeo. You enjoy the wind in your hair, the driving experience, the scenery, good food and the unique wines of Chianti.

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