Diego Della Valle's Gulfstream lands in Milan during fashion week after a short hop from Marche

Diego Della Valle's Gulfstream G550, tail I-ADVD, was tracked flying from Marche Airport (LIPY) to Milano Linate (LIML) on 20 September 2026, a 40-minute hop that reached 28,025 feet and a ground speed of 465.9 knots. The aircraft, managed by Milan-based operator Sirio and bearing a registration suffix that mirrors the owner's initials, is the primary business jet linked to the Tod's Group chairman. As with all European civil registrations, the beneficial owner is not publicly recorded, but the tail code and operator filing point to the same person who turned his grandfather's cobbler's workshop into a global luxury house.

If Diego Della Valle was aboard, he would have arrived in Milan the same week the city hosts fashion week — an event where Tod's presented its Spring/Summer 2027 collection at Villa Necchi Campiglio. Per a report from LaConceria, Della Valle spoke on the sidelines of that presentation, declaring that "the worst is behind us" and that luxury is prepared to withstand further shocks, with perhaps two or three more crises over the next decade. The flight from Marche, home to the Tod's factory in Casette d'Ete, to Milan would be a natural route for a chairman who remains deeply involved in brand strategy even after stepping back from the CEO role following the group's delisting in 2024.

Just two days before this flight, on 18 September, Diego Della Valle was quoted by Teleborsa during the inauguration of Bocconi University's academic year, where he discussed the group's plan to "valorize every single brand" and reiterated that luxury firms must be ready to "play counterattack" when markets complicate. He also dismissed speculation about a possible Armani acquisition, saying Giorgio Armani "wouldn't have sold anything" and that Tod's needs time and energy to develop its own brands. The Bocconi appearance and the fashion week presentation together form a plausible itinerary for a chairman who, as Monocle noted in a profile, keeps a packed travel schedule and shuttles regularly between Marche and Milan.

The pattern of short-haul hops between Marche and Milan is consistent with Diego Della Valle's known routine: the Gulfstream has flown this corridor multiple times in recent weeks, including a 7 September leg from Marche to Linate and a 5 September return. While the aircraft also ventures to Paris and other European capitals, the Milan–Marche axis remains the most frequent, reflecting the chairman's dual focus on the Tod's headquarters in the Marche region and the fashion and financial hub of Milan. Whether for a collection preview, a university speech, or a boardroom strategy session, the flight fits a man who, as he told Monocle, believes successful companies must assume a "leadership role" — and who still prefers to move at the speed of his own jet.