At the Maxi Yacht Rolex Cup, the number seeking boats each year can be up to a few dozen, and for many it can be a challenge.

Each year the Yacht Club Costa Smeralda , which has hosted the race for 30 years , posts a page online connecting skippers and crew members, along with the list of entrants, rules and regulations. For some sailors, it is their best shot.

Marco Brandon Rossini , 19, a business student from Milan who said he had sailed since he was 6 years old, has been seeking to crew on a boat at this race for the last three years.

Rossini grew up sailing in his hometown, Pesaro . Like many teenagers, he has mostly sailed dinghies. He sailed competitively on club teams and has raced in national and world championships. He has instructed students in a sailing school and cruised 40-footers with his family in the Mediterranean, exploring the Italian archipelagos. Last summer, Rossini said, he made his first ocean crossing on a 50-footer, sailing to San Francisco from the Hawaiian island of Oahu.

He had experience, but he still could not get a spot.

“You have those huge Maxis with powerful backers that don’t take anyone on unless they’re professionals with years of experience,” Rossini said. “You more likely to get a shot with one of the smaller boats. Nobody gives credit to a kid just 19 who’s passionate for sailing, but without much experience.”