There’s something undeniably romantic about vintage cars winding their way through Italy’s most scenic landscapes. I recently had the opportunity to experience this firsthand, cheering on my husband and his manager as they participated in the Coppa Milano-Sanremo, one of Italy’s most iconic historical car rallies. This event is far more than a parade of beautiful cars – it’s a journey through history, precision, and Italian culture.


History of the Rally
The first Coppa Milano–Sanremo took place in 1906, originally conceived as a test of speed and endurance connecting northern Italy to the Ligurian coast. Over a century later, the rally has evolved into a regularity race, where precision takes precedence over speed, but the spirit still remains unchanged!
Today, the event brings together an extraordinary lineup of historic vehicles. You’ll see everything from Alfa Romeos and Fiats to Porsches and Ferraris, each car carefully preserved (some with full teams of mechanics in tow) and ready to come alive on the road. The rally unfolds over two full days, with the cars weaving through roads across Lombardy, Piedmont, and Liguria, with multiple checkpoints and challenges along the way.
The Experience Begins!
The experience begins before the official start. The day prior, teams gather at the legendary Autodromo Nazionale Monza (a track Formula 1 fans should be familiar with) where drivers have the rare opportunity to push their vintage cars to the limit. It’s an epic contrast: historic vehicles speeding around one of the most modern and iconic circuits in the world.
Later that evening, everyone reconvenes in Milan for the official kickoff dinner. In true Italian fashion, the evening is as much about connection as competition. Glasses of Franciacorta are raised, stories of previous races are shared, and there’s a shared sense of anticipation for the journey ahead.
The next morning, bright and early, the rally begins. Cars depart one at a time from the starting line in Milan, slowly making their way toward the coast.
Precision Over Speed
While this may sound like a leisurely drive for those on the sidelines, the Coppa Milano-Sanremo is anything but. Throughout the course, each day there are dozens of technical challenges.

Each team (the driver and copilot) are given a detailed roadbook which contains: the specific route, target speeds, and exact timing checkpoints. During the course, teams try to maintain a precise average speed between the checkpoints – arriving too early or too late (even by seconds) can incur penalties!
Factors like traffic, changing terrain from city streets to mountain roads, or lack of modern precision instruments in the cars all play a role. It’s a true test of patience and teamwork. As you can see, it is not il dolce far niente.
Crossing the Finish Line
The atmosphere shifts as the cars cross over the finish line in Sanremo. Everyone appears exhausted, having driven challenging roads and completing precision tests, yet relieved and exhilarated.


We were hosted at the elegant Royal Hotel Sanremo, a historic property overlooking the sea. True Italophiles may recognize it as the hotel that hosts many of the artists during the annual Sanremo Music Festival, the prestigious competition whose winner goes on to represent Italy at Eurovision.
Beyond the Competition
Of course no Italian event is complete without some fun! This year’s rally wrapped up with a beautiful gala at the Sanremo Casino where attendees gathered for a final dinner. Everyone gathered around tables, sharing stories about the experience and cheering on those who won awards.



Even as a spectator, the Coppa Milano-Sanremo is a spectacular event to attend. Seeing these beautiful cars up close, celebrating at historic venues, and learning the ins and outs of the challenges is exciting.
Other Italian Car Rallies
For those inspired by this experience, the Coppa Milano-Sanremo is just one of several historic car rallies that takes place in Italy. Enthusiasts can follow (or even partake in) events like the Mille Miglia or the Targa Florio. And yes, participation is open to anyone who meets the requirements, such as owning a qualified vehicle.
So whether you’re grabbing your car keys and ready to rally or grabbing your camera to snap pictures as the cars pass by, this is an Italian experience you don’t want to miss.
To learn more, visit the Copa Milano-Sanremo website.

