Like their great-grandfather, sister Meghan and Christina O'Rourke Race to Mackinac
CHICAGO (CBS) -- This is a live look over lake michigan tonight, where the annual Race to Mackinac begins this weekend.
The 333-mile race from Chicago to Mackinac Island, Michigan, is steeped in tradition, and it also runs in the family for a couple of sisters hoping to return the family name to sailing glory.
CBS 2's Noel Brennan shares their story and the brothers who came before them.
"It's a little all over the place, Meg. What do you think? Right in front of Chicago, it looks like it's coming out of the South, which is exactly what we want."
As sisters prepare to set sail, the next generation soaks it all in.
"She's either going to fall in love with it and sail, or she's going to completely hate it because of how involved, like, me and my husband are."
Sisters Meghan and Christina O'Rourke are prepping for the Race to Mackinac.
"It's a 333-mile race from the end of Navy Pier to Mackinac Island. It usually takes about two, three days. We hope it's closer to two."
In the O'Rourke family, this race tradition runs deep.
"I feel like we've heard this story probably at every Christmas dinner, like from as far back as I can remember."
"Our great-grandfather did this race a hundred years ago."
John Paul O'Rourke and his brother Jim were underdogs on water.
"He's this sailor from Jackson Park Yacht Club, and he has this really small boat for this race. A Q-boat."
The brothers sailed well in terrible conditions.
"He won the race in 1923."
But the celebration was short-lived.
"Ultimately, he got disqualified four months after the race was completed."
"It was because he didn't have the right certificate of measurement."
That was the official story.
"Back then, there was quite a bit of money on the race, quite a bit of gambling, and so there were some thoughts about maybe those with influence maybe wanted to change the outcome in their favor."
A century later, the truth may still be a bit murky.
"I feel like part of the fun of the story is the debate, is the fact that we'll probably never have a sure answer."
Christina and Meghan now carry-on tradition from separate boats.
"I feel like both of us would not make it to the island."
"For the sake of our relationship, we sail against each other."
Sisters set sail for victory, like the brothers who came before.
Pre-race events are starting Thursday. The official race sets sail Saturday - with more than 250 boats participating.