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Paul Cayard

About Paul Cayard

Paul Cayard is one of America’s most recognized and accomplished sailors.

Cayard, an eight time world champion, seven time America’s Cup competitor, has twice circumnavigated the world, becoming the first American to win the Whitbread Round the World Race in 1998, and placing second with the Disney syndicate Pirates of the Caribbean in the 2005-2006 edition of the Volvo Ocean Race. He is a two time Olympian (1984 and 2004) and one of the very few who have competed at the top level in these three diverse disciplines within the sport of sailing.

With hundreds of thousands of miles at sea over the past 40 years, Cayard’s sailing exploits from the America’s Cup to the Roaring 40’s and the icebergs of the Southern Ocean have given him a wealth of experience, proving his leadership skills sometimes in harrowing moments in the Southern ocean where lives were on the line.

Beyond his skill at the helm, Cayard is one of the sport’s pioneers in marketing and the management of sailing teams which includes working with Fortune 500 companies such as Disney, Ford, and United Technologies. Cayard is also a sought after public speaker, his ability to recount fascinating and life changing moments at sea has captivated audiences all over the world. Fluent in English, French and Italian, Cayard frequently speaks at conferences around the globe and commentates on sailing including during the 32nd America’s Cup in 2007 for RAI.

A Rolex Ambassador since 1999 Cayard also has endorsed various brands including Oakley and Zegna.

Cayard’s accolades include induction to the National Sailing Hall of Fame in 2011, Bay Area Sports Hall of Fame in 2020 and the America's Cup Hall of Fame in 2025.

Cayard was born in San Francisco and currently resides in La Jolla.

Entries by Paul Cayard

Cayard Sailing Reports

Star World Championship 2016

Coconut Grove Today was the final race of the 2016 Star World Championship.  The wind was slow to build but finally came in at 7-8 knots from 060.  It was blowing over Key Biscayne onto the course and this made for very shifty conditions and significant deltas of wind pressure. After several attempted starts, we […]

April 16, 2016/by Paul Cayard
Cayard Sailing Reports

Star World Championship

Coconut Grove Race 5 was held yesterday in a light 7-8 knot breeze from the south east.  The sun was out, the sea was flat and warm.  It was classic Star sailing on Biscayne Bay. After three general recalls of the start, the Black Flag came out and  3 teams were caught out by this.  Brian and I […]

April 16, 2016/by Paul Cayard
Cayard Sailing Reports

Star World Championship

Battling the kelp today. Marco Oquendo photo Coconut Grove Race 4 was held today for the 73 competitors in the Star World Championship on Biscayne Bay.  The winds were light again blowing in from the southeast at 7-8 knots. I felt like it was going to be good on the left today so we started […]

April 15, 2016/by Paul Cayard
Cayard Sailing Reports

Star World Championship

Skin cancer awareness has hit the Star Class and we are all wearing these neck and face covers. Photo was from Race 2. Photo by Marco Oquendo. Coconut Grove Day 3 of the Star World Championship started off without wind.  The fleet waited for over an hour before we could attempt to get a race started. […]

April 13, 2016/by Paul Cayard
Cayard Sailing Reports

Star World Championship

Coconut Grove Race 2 of the 2016 Star World Championship was held today on Biscayne Bay.  At start time, 11:30, the wind was in at 16 knots from 085 and stayed pretty much the same all race.  Having said that, there were 15 degree oscillations and 4 knot changes in windspeed.  It was still a […]

April 11, 2016/by Paul Cayard
Cayard Sailing Reports

Star World Championship

Coconut Grove Coral Reef Yacht Club is hosting the 2016 Star World Championship this week.  75 boats from 13 countries are competing with 8 former World Champions in the lineup. The format is one race a day with a lay day mid way through the week. Today was the first race. The wind was blowing 16 […]

April 11, 2016/by Paul Cayard
Cayard Sailing Reports

St. Barths Bucket Final

St. Barths, French West Indies Another perfect day today with winds a bit further right coming out of 130 at up to 20 knots. The course for the final race was clockwise around the archipelago of St. Barths. For the third time, Peter Holmberg and I devised a good strategy to get clear of the […]

March 20, 2016/by Paul Cayard
Cayard Sailing Reports

St. Barths Bucket

St. Barthelemy French West Indies Another beautiful day for sailing down in the Caribbean.  Today the winds were slightly more to the right at 110 and 15 knots. The course for the today is known as the “not so wiggly” course.  The fleet starts downwind to the west and goes around some rock at the […]

March 20, 2016/by Paul Cayard
Cayard Sailing Reports

St. Barths Bucket

Saint Barthelemy, French West Indies Today was day 1 of the 2016 Super Yacht Bucket.  I am sailing onboard Rosehearty with Joey Kempfer for the third time in a year.  36 Super Yachts are here racing divided into 5 classes.  Super yachts are yacht more that 100 feet in length and typically quite luxurious. Rosehearty is […]

March 18, 2016/by Paul Cayard
Cayard Sailing Reports

89th Bacardi Cup

Coconut Grove Another perfect day for sailing today on Biscayne Bay with 12 knots of wind to from the southeast and sunshine. The final race was for all the marbles.  Robert Stanjeck with Fritjof Kleen (GER) up front and Diego Negri with Sergio Lambertenghi (ITA) were tied and no one else could beat either of […]

March 12, 2016/by Paul Cayard
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Cayard’s Updates

  • St. Barths BucketMarch 29, 2026 - 10:12 am
  • Bacardi Cup 2026March 29, 2026 - 9:49 am
  • Rolex Yachtsman of the YearMarch 29, 2026 - 9:31 am
  • America’s Cup Hall of FameDecember 20, 2025 - 5:20 pm
  • Star World Championship-2025December 20, 2025 - 5:10 pm
  • Time to TackFebruary 25, 2023 - 3:48 pm
  • US Olympic SailingMay 7, 2021 - 9:00 am
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RSS Sailing Scuttlebutt

  • Callahan/Davis claim Snipe US Nationals
  • This was really like coming home
  • IOC rejects crossover sports for now
  • Thirty years later: Michael Blackburn
  • Behind the Scenes, June 2026
  • 2026 Flying Scot North American Champs
  • It’s not a sport, it’s a discipline
  • Perpetuating the past can be good
  • I’m not asking for perfection
  • Epic battle for TP52 World Championship
Popular
  • Project Pipeline AnnouncementFebruary 5, 2015 - 7:10 pm
  • St. Barths BucketMarch 29, 2026 - 10:12 am
  • AmericaOne-Challenger America’s Cup XXXJune 1, 1996 - 12:00 am
  • MaxisOctober 1, 1996 - 12:00 am
Recent
  • St. Barths BucketMarch 29, 2026 - 10:12 am
  • Bacardi Cup 2026March 29, 2026 - 9:49 am
  • Rolex Yachtsman of the YearMarch 29, 2026 - 9:31 am
  • America’s Cup Hall of FameDecember 20, 2025 - 5:20 pm
Comments
  • LarryPaul Thanks for the tribute to Bob. LarryFebruary 6, 2015 - 1:18 am by Larry
  • MikeThank you for this! I didn't know Bob at all well, but...February 6, 2015 - 1:17 am by Mike
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