Sail in Your Own America’s Cup Yacht Race in San Diego Bay

Set sail on Stars & Stripes—one of the most famous America’s Cup yachts in the world.  At a length of nearly 80 feet and with a mast over ten stories high with 3,500 square feet of sails, she is a combination of speed and stability. Stars and Stripes USA-11 was skippered by Dennis Conner in the Defense Series of the 1992 America’s Cup. Conner’s Stars & Stripes boats raced in five America’s Cup races and won the trophy twice.

You and your team can now relive Cup history with a private charter of this iconic yacht.  With space for up to twenty guests, your team will actively sail this boat together with the professional skipper and crew.  Six of your mates will raise the massive mainsail by grinding the pedestal winches (coffee grinders). Your team will also help to trim the sails, tack and jibe in different headings, and the most fun job of all—steer the boat.


America’s Cup Race in San Diego Bay


Recreate the 1992 America’s Cup in San Diego with Stars & Stripes  against the challenger boat from Italy, Il Moro di Venezia.  Sail your two teams against each other for this ultimate competition on world class boats.

Why not have the original skippers command your crew?  Add world famous Stars & Stripes skipper Dennis Conner and Il Moro skipper Paul Cayard.



Team Stars & Stripes 

Dennis Conner or Peter Isler will join your team on this sail of a lifetime.

Dennis Conner

Dennis Conner is a living legend in the history of sailing, His nickname of “Mister America’s Cup” comes from his singular impact on the modern Cup. Conner sailed in ten America’s Cup campaigns and won the Cup for the United States four times. He has also sailed in the Olympics (won bronze) and 28 World Championships.

Peter Isler

Peter Isler was navigator on Stars & Stripes and has sailed in five America’s Cup campaigns, winning it twice.  He also founded two America’s Cup teams including the America3 All Women’s Team.  Internationally renowned in sailing with numerous racing records, he is also a television commentator for ESPN and ABC Sports, best-selling author and motivational speaker to Fortune 500 companies.

Paul Cayard

Paul Cayard is a seven time world champion and seven time America’s Cup competitor. He was the skipper of Il Moro in the 1992 America’s Cup.   He has twice circumnavigated the world and became the first American to win the Whitbread Round the World Race in 1998.  With hundreds of thousands of miles at sea over the past 40 years, Cayard has captivating stories from the America’s Cup to the Roaring 40’s and the icebergs of the Southern Ocean.   Fluent in English, French and Italian, Cayard frequently speaks at conferences around the world.   Hear his stories up close as he skippers Il Moro with your team in San Diego Bay.