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Italy
4 days

Mille Miglia Tour 2027: Tuscany in an Alfa Romeo Spider

Tuscan Roads Following the Spirit of the Mille Miglia

June

About This Tour

Experience the Mille Miglia 2026 from behind the wheel of a classic Alfa Romeo Spider. This guided Tuscany driving tour follows the legendary roads of Italy’s most famous historic race through Chianti, Siena, Pienza, and San Gimignano. Drive scenic Tuscan backroads, visit medieval towns, enjoy regional food and wine, and witness the Mille Miglia up close in the car brand that won it more than any other.

1
Driving Through Chianti in an Alfa Romeo Spider

Your journey begins with arrival in Florence and transfer into the rolling hills of Chianti. After lunch and a detailed introduction to the Alfa Romeo Spider fleet and roadbook navigation, you set off on your first Tuscan drive. Quiet country roads wind through vineyards, cypress avenues, olive groves, and hilltop villages. During the afternoon, you visit a historic monastery known for centuries of winemaking tradition before returning to your hotel for a relaxed evening in the Tuscan countryside.

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2
Experience the Mille Miglia Up Close

Today, Tuscany becomes part of the Mille Miglia. More than 400 historic cars pass through medieval villages and rolling landscapes as the legendary “Corsa più bella del mondo” crosses the region. Only vehicles built before 1957 are permitted to participate, preserving the spirit of the original race. From behind the wheel of your Alfa Romeo Spider, you experience the atmosphere from inside the event itself. No manufacturer achieved more Mille Miglia victories than Alfa Romeo, making this one of the most authentic ways to experience the race today.

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3
Val d’Orcia, Pienza & the Crete Senesi

Today’s route follows portions of the historic Via Cassia and stretches once used during the original Mille Miglia. South of Siena, the landscape opens into the UNESCO-listed Val d’Orcia, one of Tuscany’s most celebrated driving regions. In Pienza, Renaissance architecture and panoramic countryside views create the perfect setting for lunch. Later, the road climbs through the dramatic Crete Senesi, where winding ridges, cypress trees, and lunar-like clay hills create one of the most recognizable landscapes in Italy.

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4
San Gimignano & Medieval Tuscany

The final driving stage leads west toward San Gimignano along quiet Tuscan roads once connecting Siena and Florence. Famous for its preserved medieval towers, the town earned the nickname “Manhattan of the Middle Ages.” During a guided visit, you explore the UNESCO-listed historic center before enjoying time for lunch in the old town. The journey concludes in Monteriggioni, where you return your Alfa Romeo Spider before transfer back to Florence Airport or your hotel.

Italy

Tuscany – The Perfect Region for a Classic Alfa Romeo Tour

Tuscany combines some of Italy’s finest driving roads with world-famous scenery, food, wine, and culture. Vineyards, olive groves, cypress-lined roads, and medieval villages create a landscape that feels timeless, especially from behind the wheel of a classic Alfa Romeo Spider.

The Mille Miglia in Tuscany

The Mille Miglia remains one of the world’s most celebrated historic motoring events. Tuscany offers one of the most scenic sections of the route, where historic race cars pass through hill towns, vineyards, and countryside roads much as they did decades ago. Experiencing the Mille Miglia in an Alfa Romeo is particularly fitting, as Alfa Romeo remains the most successful marque in the history of the race.

Siena, San Gimignano & Tuscan Culture

Historic towns such as Siena and San Gimignano preserve much of their medieval identity. Siena’s famous Palio horse race remains one of Italy’s great cultural traditions, while San Gimignano’s towers dominate the skyline much as they did centuries ago. Across the region, Roman roads, fortified villages, and Renaissance architecture remain part of everyday life.

Tuscan Food & Wine

Chianti wines, handmade pasta, pecorino cheese, olive oil, and local trattorias define Tuscan cuisine. Family wineries, historic monasteries, and countryside agriturismi remain central to the region’s culture and hospitality, making Tuscany one of Italy’s most rewarding culinary destinations.

Included

  • Group transfers from and to Florence Airport (FLR)
  • Self-drive classic Alfa Romeo Spider including fuel and fully comprehensive insurance (€2,500 deductible)
  • 3 nights with breakfast at Villa Curina****, Castelnuovo Berardenga
  • 1 lunch
  • 2 dinners
  • 1 wine tasting
  • Admission fees and guided sightseeing according to itinerary
  • English-speaking guide and support team throughout the journey
  • Welcome gift

Not Included

  • Flights and travel to Florence (FLR)
  • Meals unless otherwise stated

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.

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 Vesiclne 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

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

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Mille Miglia Tour 2027: Tuscany in an Alfa Romeo Spider