No, it does not mean you are required to have at least two of your teenage sons aboard.
There is an organization/system called PHRF, Performance Handicap Racing Fleet, which assigns individual handicap numbers to boats based on the boat's design, sail plan and equipment (roller furler, folding prop, etc. . .). These numbers translate into seconds per mile figured against the other boats' ratings. A boat with a rating of 120 would owe a boat of 130 ten seconds per mile. There are separate numbers for spinnaker and non-spinnaker races.
This system allows owners of different kinds of boats to compete on a more or less equal playing field (though we all grumble that the other boat's rating is too generous and ours too restrictive). The other alternative for providing a level playing field is for sailors to congregate in fleets of the same boat design fitted out within exact rules, class racing. But not everyone wants to own a J-24, Rhodes 19, Laser or whatever.
With the handicap it often occurs that you cross the finish line minutes after another boat and still beat them. The most fun is when we race boats whose rating is close to ours. This way we all get the excitement of side-by-side racing.
Narragansett Bay PHRF
(In all fairness, our kids are pretty darn good sailors, even if they are knuckleheads.)
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