He enjoys flying and holds a pilots certification with instrument rating for both single and multi engine aircraft.

Sailing in the Star Class, he won the silver medal at the pre-Olympic regatta in 2003, going on to finish 5th at the 2004 Summer Olympic Games in Athens.

His top achievement in this arena was becoming the first American to win the Whitbread Round the World in 1997-1998 as skipper of EF Language.

In 2005–2006, Cayard competed in the Volvo Ocean Race as skipper of the Pirates of the Caribbean syndicate sponsored by The Walt Disney Company in reference to the movie of the same name.

Cayard Sailing Inc. managed the team which won the final leg into Gothenburg to finish the overall race in 2nd place.

In 2007, Paul Cayard and Russell Coutts announced the launch of the World Sailing League in partnership with internationally renowned Portuguese sports promoter, João Lagos.

[2] For the 1992 America's Cup, Cayard was manager and skipper of Il Moro di Venezia from Italy, a syndicate backed by Raul Gardini.

Though Il Moro di Venezia was outclassed in the America's Cup races by the faster America³, Cayard's expertise in sailing provided some memorable moments.

In 1995, Cayard joined an American effort for the America's Cup with Team Dennis Conner Stars & Stripes as primary helmsman.

In an unprecedented move, Team Dennis Conner decided to use the faster yacht Young America from the PACT 95 syndicate to defend the Cup.

However, equipment fatigue and failure proved decisive, several spinnakers were blown out, and Prada ended up winning the next two races and the series, 5–4, earning the right to challenge for the Cup.

For the 33rd America's Cup, Cayard provided commentary for Eurosport and in 2009 joined Torbjorn Tornqvist's sailing on Artemis Racing for the TP52 and Louis Vuitton Trophy regattas.

In 2020, Paul Cayard was the first sailor to be inducted into the Class of 2020 for the Bay Area Sports Hall of Fame, (BASHOF)[6]