This reminds me precisely of what it's like to do the
'Rough Rider Regatta', especially when it used to go up the intercoastal waterway, for about a hundred miles.

There was usually a 'continuous obstruction' from the shallows outside the channel.

People that knew the rules played it fair, and sometimes a line of 3 or 4 boats would have to tack, b/c the lead boat was nearing the 'obstruction'- shallows.
That was usually about 10 boats out of 100+!

They even put the rule verbage in the NOR and R.I. at least one year.

Those were the days!