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4 days

Mille Miglia Tuscany Driving Experience – Alfa Romeo

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
  • Detailed road book and tour materials
  • 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.

Fabulous trip

First, I want to thank you for a wonderful experience and offer my praise for putting together a fabulous trip. I will miss some superlatives but they include: able escorts (not strong car guys but attentive hosts), well thought out routes and the “bicycle” route guides for same, the thoughtfulness of supplying an auxiliary phone power source, pleasant and well situated lodging at the NH in Palermo and near Mount Etna, some insanely bountiful lunches and a fabulous Michelin Star experience on our last night – all nights but the first (a great atmosphere but average fare) measured up to our last meal, prearranged and easy to find parking in Taormina, a fabulous, knowledgable and articulate guide in Palermo, scripted menus, nocturnal tours and, of course, the opportunity to drive a different Alfa each day. Criticisms are few but you have asked for same: I found the hotel near Cefalu to be consumer unfriendly and most occupants were concerned and discomfited by the malodor of unburned petrol – might I suggest in line filters for the gas tank vents.

Mark Moskowitz,

NC USA

Unforgettable experience

We returned home safe and sound Thursday evening. The real world starts Monday, but before events take over I wanted to let you know what an unforgettable experience our Grand Tour was. Please extend our heartfelt thanks to everyone who worked so hard behind the scenes to make it possible: those we saw, and those we didn’t. You make it look easy. We know better. Pulling this off is hard, hard work and it involves a lot of flexibility and gymnastics. On a scale of 1-10 we’d have to rate our trip as a 15.

Vern Herr,

Norcross GA USA

Felt okay driving them with verve

The Alfas were great. They were in good condition, but not perfect, so we felt okay driving them with verve. The routes were beautiful and well planned. The gift bag items were nice and very useful. The balance of group and individual meals was good. Noel and Luca communicated very well with everyone. Well done.

James Peltier,

Indiana USA

My son and I had the most special time

Let me just say that my son & I had the most special time together on this magical trip. The scenery, cars, roads, hotels, food and staff were more than exceptional! The group was full of car geeks and we enjoyed their company. We look forward to another journey in the future with Nostalgic.

Stuart Gollomp,

Westport USA

The cars were superb

My wife and I just finished a great 4 days in Italy driving your Alfas. Your team was fantastic! The food was outstanding. We probably bought too much organic wine. We look forward to drinking and remembering this trip. The cars were superb. My wife thought I was losing my mind when I was laughing through the winding roads of Umbria. Thanks again to you and your staff. Alex and Fabio deserve a special thanks. They went above and beyond to make the trip memorable. Until the next trip.

Michael Crowley,

Texas USA

Words cannot communicate this experience

I had travelled to Lago Maggiore many times during my life. The Nostalgic team was able to assemble a life experience which brought all elements of wonderful scenery, great cars and great roads together for 23 people from all parts of the world to enjoy. While we may all mat have come from various countries, spoke different languages and diverse backgrounds, age and cultures, we all bonded on this level of life experience. Words cannot communicate this experience and can only recommend one to try for themselves. I would do this tour again (and I will) in a heartbeat!

Darius Oggioni New Jersey,

New Jersey

You’ve inspired me!

It was our first trip to Italy, and we feel it was a much more real taste of the country than we’d ever experience following a traditional tourist itinerary. Driving classic cars through the mountains, valleys, and lakeshore was incredible — we saw so many people looking at us jealously! But as great as the cars and countryside were, the people made the tour special. We appreciated the support of the Nostalgic team. We quickly bonded with fellow travelers and anticipate staying in contact. Not only are we considering our next trip with Nostalgic, I’m thinking of scenic routes to plot in my home region — both for my enjoyment and for friends. You’ve inspired me!

Paul Kurmas,

Vermont USA

Lake Maggiore was magical

Lake Maggiore was magical. The setting was more than I expected. Day 2 drive up to Lago d’Orta was lovely. The dappled sunlight through the trees and the gorgeous greenery. And then the lake itself and the magesty of the mountains around us. Mezmerizing. Although times precarious, the drive to Locarno was breathtaking, literally at time as we rounded a corner the view was indescribable. And when we came upon the festival in the town just south of the midpoint stop (Rainbow disco church as we called it). Ascona was my favorite stop.

James Kelly,

California USA

A perfect experience!

It was a perfect blend of structured time/group time and individual. The cars were amazing, guides were amazing, routes were great, tours/towns visited were perfect. It has a real world feel as we drove among actual Italian villages and a surreal element as passersby photographed us in the cars. A perfect experience!

Nate Potter,

Cincinnati USA

It was truly beyond belief!

The time we had with our family is beyond words. The event itself was just fantastic. Your accommodations for us after the tour were over the top and eased our angst. We look forward to another trip with Nostalgic Tours in the future. It was truly beyond belief! Thank you so much for everything,

Edward and Debra Kammrath,

Indiana 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 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

Beautiful old property

We enjoyed both of our wonderful tours with Nostalgic. The first was in Tuscany. We were greeted at Florence airport and taken by private coach to our base hotel a few miles from Siena. It is a beautiful old property with an excellent restaurant and kitchen. All our needs and wishes were attended to by Walter and his staff. Our cars were clean and ready every morning for the day’s drive. All the routes were conducive to relaxed, uncongested driving. The lunch and dinner venues were outstanding.

Jack Brewer,

Florida USA

Meticulous attention to detail

Our base hotel accommodation was premium. Walter and his staff had arranged spectacular drives through the Alps Maritimes and the Route Napoleon. As expected, the cars were in impeccable condition. The selection of side tours, points of interest, rest stops and restaurants were excellent. Every meal was memorable. Walter and his staff looked after us in every situation. They engender a level of confidence and enthusiasm that is made possible only by thorough planning, years of experience and meticulous attention to detail…..and an uncanny ability to anticipate the wishes and expectations of their clients. In addition to the wonderful experience that the tours offer, we have made close friendships among those with whom we shared these experiences. This is an unexpected and priceless reward. We are eagerly anticipating our next nostalgic.de experience.

Diana Brewer,

Florida USA

Tremendous amount of fun

Driving the Alfa Giulia Spider on these roads was magnificent, a tremendous amount of fun. The cars were genuinely in very good condition, engine, drive train, all good. All really went well, the road books were very well done even to us who were not familiar with all the signs on the roads in Europe. The guides were enthusiastic and contributed very well to the experience. I liked not having to follow a lead car but to be responsible myself for all directions. I did not feel as on a group tour, even though we made friends with some of the other couples on the tour.

Jay Maveety,

Fairfew City USA

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Mille Miglia Tuscany Driving Experience – Alfa Romeo