The Rolex Swan Cup Is One of Sailing’s Most Illustrious Races. Here’s What It’s Like to Attend.

Every two years, more than 100 owners and crews of the world’s most sought-after sailboat brand come together for the Rolex Swan Cup, a five-day race series held at the Yacht Club Costa Smeralda. The regatta takes place on the northern coast of Sardinia, with its famed Mistral winds, and attracts owners from three continents to compete for two sweet prizes—a Rolex watch and, equally as important, winner’s bragging rights.

This year’s cup, the 22nd iteration that ended Sunday, had 101 boats attending. But it was unlike others in the Swan Cup history, involving the departure of Nautor Swan president Leonardo Ferragamo, who announced he was leaving the company after 36 years.

The Swan Cup is one of multiple events held each year for Nautor Swan owners. Costa Smeralda’s superyacht marina is packed with Swans bearing the familiar arrow on their hulls. Green Rolex flags fly on the masts, flapping in the breeze, and even the superyachts in the area are upstaged by the packs of Swans racing against each other, many with billowed black sails, around the area’s stunning waters.

“Every day the boats go all around the islands on different courses, which depend on wind conditions,” Federico Michetti, head of sports activities at Nautor Swan, told Robb Report at the event. “They are scored based on position, so if there are 15 boats and yours is first, you get one point. Last place gets 15.” The lowest scorer by the end of the week is the overall winner. 

The boat classes range from Maxi yachts to the historic S&S Classic group to multiple One Designs—boats with the same hull configurations and weight that make racing a game of skill rather than superior technology. “In the one-class, the sailors are what differentiate the winners from everyone else,” says Michetti.

Nautor Swan has been building high-end, fast, and luxurious sailboats (and recently two motorboat models) since 1969. The brand established its presence after the Swan 65 Sayula II won the first Whitbread Round the World Race in 1973/74. In 55 years, the builder has only had three yacht designers, but all are icons in the sailing world: Sparkman & Stephens, responsible for designing the first 1,000 hulls, Ron Holland who did three different lengths, and for the last 40 years, German Frers, who has developed many iconic Swans.

Fashion magnate Leonardo Ferragamo, who purchased the yard in 1988, has transformed Nautor Swan into the luxury cruising/racing brand in the sailing world. Ferragamo is retiring after selling to Sanlorenzo Yachts earlier this year. But his 36-year-history is noteworthy for not only expanding the brand across multiple segments (from the custom 131-foot Custom Maxi to the recent Nautor 28) but also enhancing both the luxury and technical components of the fleet. It launched its first hybrid yacht in April.

Ferragamo was also tireless in establishing a Swan race circuit with an average of six to eight annual events in different yacht clubs, typically in glamorous locations. This year, 101 Swans of all sizes from 30 countries made the trek to Porto Cervo, hailing from different European countries, California, and Japan.

Ferragamo also races his hunter-green Swan 50 Cuordileone, and this year the boat had pride of place at the superyacht marina in Yacht Club Costa Smeralda. “When choosing my first yacht, I decided to buy a Swan, specifically because I wanted to take part in the Swan Cup,” he tells Robb Report. 

The event has improved every year, Ferragamo says, thanks to the participation of Rolex, which has long sponsored sail-racing events around the world. “We’ve been able to bring three marvelous brands, Rolex, Yacht Club Costa Smeralda, and Nautor Swan into one event,” he says.

The Rolex Swan Cup is by invitation only for Swan owners, attracting more than 700 sailors and a few hundred loved ones as well as many race-sponsor clients. In the mornings, owners and their crews buzzed around the docks, readying giant, high-tech sails, tying off lines, and loading gear. Many teams were easily identifiable in what amounted to colored uniforms, donning matching UV shirts in ocean blue or bright yellow. A few local yachties watched the preparations, almost meditatively, from their decks, enjoying fresh cornettos and espresso.

Racing is intense, with staggered starts to allow the non-class boats time to move through the racecourse, while one-designs often jockey for position, usually aggressively, to lead their groups. There is intense peer pressure among owners to win this cup, mostly with skillful captains and crews, but sometimes the right puff of wind can make the difference between first and second place.

Californian Don Macpherson comes to Sardinia every two years to race in the Cup. His racing career started as soon as his 50-foot Freya was launched 12 years ago. He originally had a professional captain, but with the help of a crew that now includes his children, he chases grand prizes by skippering the boat himself. Macpherson also races in the Caribbean (where he’s headed after Sardinia) but considers the Swan Cup the “premier” racing experience. “There is no place better to sail than Porto Cervo,” he tells Robb Report. “The club here does a fantastic job organizing events.”

Freya, easily identifiable by its yellow sails, has come a long way in the last decade. “In the first race, we came in dead last,” Macpherson recalls. “Then we did better and better.” So much so that his boat won the ClubSwan 50 division in 2016, 2022, and again last week.  

Fellow Californian Al Ramadan hopes to have a similar record one day. He is the newest Club Swan member, but he wasn’t able to sail his Swan 28 until a week before the race, since it had just been delivered to Italy from the factory. His shakedown cruise was from the mainland to Sardinia, with a five-person crew aboard. Like many sailors, Ramadan had always been attracted to Swans. He was determined to own one and race it someday.

From the outside, Ramadan notes, the Nautor Swan community can look pretentious, unapproachable. But in Sardinia, he had an entirely different experience. “I went to the parties, and they were very glamorous, but Swan is a wonderful, helpful community that I’m proud to be a part of,” he says. In other words, he was instantly adopted into the club.

The event is also about play. Parties close out the event—the first is hosted on Thursday for owners at Costa Smeralda by Nautor Swan. Ferragamo, who was effectively making his swan song this year, gave the owners special parting gifts: for the men, signature ties made for the Cup, and for the women, a silk scarf with the same pattern. The evening proved to be intimate and civilized.

But the second post-race party, hosted by Rolex, was the place to let loose, dance, and enjoy Sardinian pasta specialties made in front of you. With more than 1,000 people in attendance, the space was packed with dancing, singing sailors who were lip-synching to American Top 40 hits on large video screens.

This year’s winners, in their respective classes, included Freya, Sea Quill, Isabella, Mascalzone Latino XXXIII, Katima, From Now On, Moonlight, Ulika, Canopo, Fra Martina, and Marcello.

“The Rolex Swan Cup is not just a race,” says Michetti. “It’s a lifestyle, a state of mind, and all these guys coming from all around the world enjoy being part of the Swan family. That part always amazes me.”