Image: Illustration of Cleopatra's Barge from Peabody Essex Museum

Yachting, or sailing for recreational purposes, can be traced in the United States to George Crowninshield of Salem, Massachusetts. 
Crowninshield, described as a "swell and a dandy," was  a member of a prominent and wealthy mercantile family whose trading ships
sailed between American and European ports during the early days of the Republic. 

George built Jefferson in 1801, a 22-ton sloop which he used for pleasure sailing along the New England coast.

War with Great Britain erupted in 1812, and George obtained a Letter Marque from the Department of State to operate Jefferson as a
licensed privateer. With the end of war in 1815, George built a large 192-ton brigantine, which he named Cleopatra's Barge. She was the largest private yacht in the United States in her time and was seen frequently in the sunny European ports along the Mediterranean. With more than 11,000 miles of coast along the eastern United States, competing mercantile houses naturally began a remarkable quest for speed and efficiency in their sailing craft and ships. By the early federal period, Chesapeake Bay pilot schooners identified as Baltimore Clippers were known for their blazing speed and remarkable sea-keeping abilities. The design features which earmarked fast commerce carriers and fishing boats were adopted by the Navy Department after 1798 for their first frigates and sloops of war.

It may be axiomatic, but nonetheless true, that two boats sailing near one another will eventually begin to race.  American, and particularly New York, mercantile houses in the nineteenth century were unabashedly competitive, and their owners amassed great wealth.  It stood to reason that these merchant princes built pleasure yachts which they raced at every opportunity. This racing was not for the fainthearted, for wagers of up to $500 would be placed on any given Sunday afternoon for a Hudson River or New York Harbor contest. This racing was ad hoc with no organization, and it was strictly boat-for-boat with the winner taking the wager.