There are roads you travel. And then there are experiences that stay in your memory.

On 7 and 8 November 2026, the Milano Portofino event returns, this time in an even more evocative guise: Milano Portofino Under the Stars, the exclusive event created by OldCar24 and organised in collaboration with Scuderia Montenapoleone, dedicated to Gentleman Drivers and enthusiasts of collector cars.

An exclusive journey through Italy, to be experienced as evening falls, when the city lights give way to the allure of night-time driving.

From Milan to Portofino: PROGRAMME

SATURDAY 7 NOVEMBER — MILAN → PORTOFINO

3:30 p.m. | Crew arrival
Arrival of the crews and registration at a prestigious venue. A welcome reception will offer participants an aperitivo and a substantial snack before departure.

4:50 p.m. | Departure
The cars will leave Milan, forming an evocative convoy towards Portofino. The opening section of the route will be accompanied by a Carabinieri escort as far as the outskirts of Milan, before the convoy continues together along the road towards the Ligurian Riviera.

9:30 p.m. | Arrival in Portofino
Arrival in Portofino's magical nighttime atmosphere will be one of the event's most evocative moments. The cars will be welcomed and parked in the splendid Piazzetta, under the stars, creating a unique setting in the heart of Portofino.

Dinner | The Piazzetta and the sea
Afterwards, an exclusive dinner will be held at a renowned restaurant in the Piazzetta, overlooking the sea, in a private and refined setting.

At the end of the evening, the cars will be stored indoors, while the crews will make their way to the prestigious hotel in Portofino, where they will spend the night.

SUNDAY 8 NOVEMBER — PORTOFINO → MILAN

10:30 a.m. | Departure from Portofino
After breakfast at the hotel, the crews will set off again in convoy towards Milan, accompanied by the convivial atmosphere that characterises the entire event.

12:30 p.m. | Lunch and awards
Arrival at a prestigious venue, where lunch will be served and the awards ceremony will take place, marking the conclusion of this special experience dedicated to Gentleman Drivers and their cars.

4:30 p.m. | Arrival in Milan
Return to Milan and the conclusion of Milano Portofino Under the Stars, after a journey through elegance, automotive passion, conviviality and the magic of the Riviera.

Only 20 Gentleman Drivers

Milano Portofino Under the Stars will be a limited-entry event, reserved for just 20 Gentleman Collectors, selected together with their cars.

Limited participation is an integral part of the event's philosophy: a small group of enthusiasts, selected cars and an experience built around the pleasure of driving and sharing the same passion.

Not simply a motoring event, but an exclusive tour dedicated to those who see the automobile as a true expression of style, culture and passion.

An experience by OldCar24

The event draws on the experience of OldCar24, an international platform dedicated to the world of collector cars, and its collaboration with Scuderia Montenapoleone.

Milano Portofino Under the Stars aims to offer a new way to experience the automobile: not only through the car itself, but through the journey, the destinations, the people and the emotions that a great automobile can create.

Milan and Portofino, two iconic places of Italian style, will thus be united by a night dedicated to Gentleman Drivers.

An exclusive event to be experienced behind the wheel

Night-time roads, collector cars, the Ligurian Riviera, the arrival in Portofino's Piazzetta and a dinner reserved for a small group of participants.

Milano Portofino Under the Stars was created to be much more than a simple motoring event: it is an exclusive experience dedicated to those who love cars, driving and the allure of Italy's great destinations.

Limited-entry applications

Places are limited to 20 Gentleman Collectors.

To apply for participation with your car:

eventi@oldcar24.com