Italy
4 days

Mille Miglia Tour 2027: Tuscany in an Alfa Romeo Spider

Rolling hills, historic villages and Italy's greatest motoring tradition

June

About This Tour

On this tour to the Mille Miglia you will experience automobile history up close. The legendary “Mille Miglia” oldtimer rally with several hundred participating oldtimers makes the hills of Tuscany shake. You will be there live at the Mille Miglia, in style at the wheel of a 1950s Alfa Romeo Spider.

1
Driving Chiantishire

We eagerly await your arrival at Florence Airport, ready to guide you to your hotel where a shared lunch marks the beginning of an unforgettable journey. After, you’ll be intimately introduced to the soul of Nostalgic’s classic Alfa Romeo Spider and the magic of navigating with a roadbook. Imagine yourself winding through the scenic vistas of Chianti, Italy’s storied wine heartland, with the top down and the breeze in your hair. The day’s highlight? An evocative visit to a historic monastery, a sanctuary of winemaking since the medieval era, where you’ll taste the legacy of centuries. As dusk falls, the evening unfolds at your leisure, offering a canvas for your own explorations or serene relaxation.

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2
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 are able to take part. Only selected cars built before 1957 are allowed, the year when the original Mille Miglia had been halted following a terrible accident. As with 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’ll be very welcome at the wheel of our Alfa Romeo Spiders when driving 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 a great driving day we will enjoy a group dinner.

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3
Pienza and the Crete Senesi

This impressive stage leads, partly on the ancient Roman Via Cassia, southwest 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 local restaurants in the old Papal town of Pienza. The highlight of the afternoon is the Crete Senesi: steep loamy slopes which resemble the moon and a onesome road running along the ridge. Dinner will be served in nearby village of Pianella.

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4
San Gimignano

The last day will still be spent driving west in the direction of San Gimignano. The winding, old Siena-Firenze country road leads you from Castellina on to Poggibonsi, and from there along side roads with little traffic to San Gimignano. The small town lies in the upper Elsa Valley and is rich in art and culture. San Gimignano is world-famous for the large number of its preserved family towers, which are mere stumps in other towns, and for its almost unchanged medieval appearance. Slender, towering spires dominate the townscape, a fact that has earned the town the nickname “Manhattan of the Middle Ages”. In 1990 the historic old town a UNESCO World Heritage Site appointed. Following the guided tour of the city, we recommend a few old town pubs for an individual lunch break before you set off on the last leg towards the Citadel of Monteriggioni set off. There, nearby, you will say goodbye to “your” Alfa Romeos and we will accompany you back to Florence airport or to the hotel if you are arriving by car.

Italy

The Mille Miglia experience it up close and personal in the most beautiful section of the “Corsa più bella del Mondo” race in the Tuscany. This is one of the most attractive regions in Italy. It impresses with its unique, multi-faceted landscape. Vineyards mix with olive groves and alternate with the original open space of the landscape. This barreness is interrupted by avenues of cypress trees, which rise slim into the sky. Little-traveled roads meander in many curves up the gentle hills and lead you through small sleepy villages. A setting like from an Italian film from the fifties.

It has also attracted culture lovers with cities like Siena and San Gimignano, as well as sights such as the Monteriggioni Fortress has a lot to offer. Already in the weeks before the world-famous horse race, the “Palio” in Siena, you may see the teams rehearsing and preparing for the big race. They parade through the city in their historical costumes and practise on their drums for the perfect entry into Piazza Il Campo.

With its impressive medieval skyline San Gimignano ranks high on Tuscany’s must-see list. The picturesque town, located at 324m above sea level, is characterized by the economic boom in the Middle Ages, which made the remarkable architecture and art development possible. It is therefore no coincidence that the historic city center is classified as a UNESCO World Heritage Site. The vineyards bordering the city walls round off the perfect Tuscan flair and give an idea of ​​the flourishing viticulture.

Included

  • Group transfer from/to Florence airport (FLR)
  • Nostalgic Alfa Romeo Spider for you to self-drive, including fully comprehensive insurance (Euro 2.500 deductible), fuel
  • 3 nights accommodation incl. breakfast in 4-star hotel Villa Curina, Castelnuovo Berardenga
  • 1 lunch
  • 2 dinners
  • 1 wine tasting
  • Admission fees, guided sightseeing according to itinerary
  • English-speaking guide and service team during the entire trip
  • Welcome Gift

Not Included

  • Travel to Florence (FLR)
  • Meals unless otherwise indicated

Our Guests Say It Best

Discover what our guests say about this tour. Real experiences from drivers and travelers who have explored Europe’s most beautiful roads with us.

Exceptional service

Exceptional service from Felix, Finn and Noel. These likable guys truly made the tour special. I appreciated the balance of autonomy and attention they provided and their overall management of the group. We absolutely loved the hotel choice and every destination. One happy surprise was our connection with the other tour members–we made some great international friends.

Ethan Whitehill,

Kansas City USA

Nostalgic definitely deserves five stars

Nostalgic definitely deserves five stars for this tour of Tuscany and the Mille Miglia! Their planning was obviously well thought out, and its execution was flawless. Who would have thought these five days would include so much of Alfa Romeos, Italy, and the Mille Miglia. Nostalgic’s vintage Alfa Romeo Spiders were in impeccable condition, and what fun driving a different Spider each day. Our tour guides made sure every detail was covered, working behind the scenes to assure the Spiders were always ready for action. They responded quickly and thoughtfully to every need and request. The Borgo di Vescine Hotel was perfect for our tour with interesting and upscale rooms and grounds and five star service and food. Finally, the whole point of the tour was driving the Alfas. They appeared to have just come from the showroom, and they drove beautifully. Thanks, Nostalgic!

Ferman Wardell,

Charlotte NC, USA

Do go!

Do go! The trips that Walter and Gert are arranging are wonderful. The cars, the food, the scenery – splendid! I went on the Tuscany tour, and loved the hotel as well. But beware, if you haven’t caught the Alfa-bug already, you might. Since my trip I now own an Alfa Romeo Giulia Super from 1973 …These cars are addictive…if possible, I will stop at Il Borgo di Véscine just to remember my visit there with Nostalgic.

Kristian Boye Petersen,

Vanlose Dänemark

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Mille Miglia Tour 2027: Tuscany in an Alfa Romeo Spider