Top Ranked TripAdvisor Boat Tours in San Diego. Sail San Diego Bay on America's Cup Stars & Stripes.

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As you’re touring our office or having the time of your life on one of our sailboats, you’re bound to hear a lot about the America’s Cup. If you find yourself wondering, “What is the America’s Cup?” we have the answer here!

The America’s Cup is the most famous and prestigious sailing regatta in the world. It is also the oldest active trophy in international sport, predating the Modern Olympics by 45 years, and is considered the “Holy Grail” of yacht racing.

The America’s Cup was originally known as the Royal Yacht Squadron Cup and it, along with a sum of 100 Sovereigns, was the prize for the 1851 Annual Regatta around the Isle of Wight, England. Though she started last, the schooner America won the race against 15 British yachts by 20 minutes. When America emerged alone from a fog near the finish, Queen Victoria asked who was second; the famous answer: “There is no second, your Majesty.”

In 1857, the American syndicate donated the Royal Yacht Squadron Cup now engraved “The Yacht America”, to the New York Yacht Club. Here it was to be held in trust as a challenge trophy to “promote friendly competition among nations.” Despite a succession of British (and other) attempts to win back the cup, the New York Yacht Club prevailed in 25 challenges over 113 years, the longest winning streak in the history of sport. Finally, in 1983, Australian businessman Alan Bond beat Dennis Conner and the cup left the United States for the first time in 132 years. But Dennis Conner refused to quit. In 1987 he challenged Australia for the San Diego Yacht Club and became the first and only skipper to win, lose, and win back the America’s Cup.

So, the next time you find yourself wondering, “What is the America’s Cup?” just remember: the cup is oldest trophy that’s still active in international sport, and it is considered to be the “Holy Grail” of yacht racing.