The enfant terrible of Italian entrepreneurship have always loved sailing

The connection between fashion, entrepreneurship, and sailing is not just an aesthetic matter, linked to places like Sardinia or the Costa Smeralda, but also a matter of anticipation. All entrepreneurs must understand and live with this trait. When embarking on a business venture, whether large or small, results are not always predetermined; often, the journey is filled with extreme highs and lows, moments of cosmic emptiness intersecting with peak excitement, where focus must never be lost—whether in periods of total calm or in the midst of turbulent climatic conditions. This is the lesson of sailing: the wind and nature are in control, not man, who must harness every bit of wind possible to outpace the competition. Perhaps this is why designers and business figures like Gianni Agnelli, Renzo Piano, Patrizio Bertelli, and the Loro Piana brothers share a common passion for the sea. Just like art collectors, these figures collect—and in some cases design—boats with the same serial enthusiasm as those who accumulate works of art.

Gianni Agnelli, heir to the family that led the Fiat group (from 1966 to 1996), is undoubtedly the emblem of this intersection between economic power and love for the sea, with hidden narratives such as his secret affair with Jackie Kennedy, wife of JFK, which inspired the name of an iconic Gucci handbag. The lawyer, as he was known to everyone, began his collection with L’Agneta: a two-masted vessel built in Sweden in 1948, with a timeless elegance, entirely crafted from fine woods. Many of the famous photos of Agnelli vacationing in the Mediterranean were taken aboard this boat. A lover of speed and a pioneer of libertines, Agnelli imposed a strict aesthetic code on his crew, who were required to wear only white linen with impeccably pressed trousers. He, on the other hand, was always half-naked, and although it is said that he was not a particularly skilled helmsman, he always insisted on taking the helm. Following L’Agneta came boats of increasingly modern and grand designs, such as when he commissioned one of the world's best designers, German Frers, to build a 36-meter yacht of a completely different style. Like Bertelli, he left his mark on Italian sailing history by participating with Azzurra (a triumph of Made in Italy designed by Andrea Vallicelli) in the 1982 America’s Cup, perhaps the most famous and celebrated regatta in the world. From there, his experiences continued, from Il Moro di Venezia by Raul Gardini to Mascalzone Latino by Neapolitan Vincenzo Onorato.

But let’s return to fashion. Moving forward, there are two other crucial figures at the very heart of our discussion. Pierluigi Loro Piana, of the Loro Piana brand, a leader in the noble fibers sector in the Biella district, who sold 80% of the company to the French group LVMH, is a lover of beauty, like all the personalities mentioned so far. His boats reach the pinnacle of perfection in terms of design and, above all, the level of performance of the selected vessels. His series of one-off yachts (models built exclusively for him) bears the name My Song, in honor of Keith Jarrett, and was entirely constructed by the two most prestigious shipyards in the world: Baltic and Nautor Swan—the latter owned by the Ferragamo group until 2024. The My Song yachts are arguably the most beautiful and elegant private sailing boats of the past twenty years. The latest model, a (relatively) smaller version, is an incredibly fast boat made entirely of carbon fiber.

We conclude with two outstanding examples of extreme passion and total dedication to the sea. The first is a Tuscan whose love for sailing surpasses any imaginable limit: Patrizio Bertelli, chairman and executive director of the Prada Group. With a personal fleet of eight yachts, all at the forefront of innovation and experimentation in sailboat design, his collection reflects his passion for design in its entirety—the pursuit of objects that, through tiny details or radical innovations, have changed the game. Beyond his eight personal yachts, we must also consider the numerous Luna Rossa boats, spanning prototypes and final versions, from 1999 to today. Bertelli is indisputably the king of this ranking, a technician of exceptional intelligence and cunning, whose skills manifest in both business and his taste for yachts, but above all in his daring investments in Luna Rossa, which, every four years—just like the football World Cup—makes Italians feel even more patriotic as they challenge the world's best teams for the America’s Cup. Perhaps little known about Luna Rossa’s endeavors is the tireless work of the entire team, which operates from a permanent base in Sardinia. Bertelli is a romantic when it comes to boats, a perfectionist in both his work and his sailing endeavors, and an extreme believer in superstition—just consider Miuccia Prada’s anxiety every time a new hull is launched, as it is bad luck if the champagne bottle does not break on the first attempt.

Finally, the most famous "Archi-star" of Italy is Renzo Piano, the Genoese architect who, in addition to designing his own Vismara yacht, has applied his deep love for the sea to architecture. This is evident in the magnificent Hermès store in Tokyo, which he designed with a glass opacity inspired by the wind’s effect over time, mimicking the salt-induced translucency seen on maritime surfaces. What unites all these figures, beyond their evident financial capabilities, is their love for this wild desire to control—while simultaneously being controlled—by forces that can be anticipated, like market analyses, yet continuously challenge them.