Hundreds of boats set sail from Chicago on Friday for the annual Race to Mackinac.             

But if you've ever stopped to look at the names of some of the boats, you may have wondered about the meaning behind the words.        

"Every year there's a time where I love it. Every year, there's a time that I ask myself why I'm doing this.

A race on open water can be relentless.

"You really have to have the patience for it."

It takes valor to sail from Chicago all the way to Mackinac Island.

"The challenge of getting, you know, 333 miles up the lake in one piece."

But the journey can catapult sailors to greatness.

"It's just experiencing the lake in a whole different way, so that's really cool."

Every crew has a boat. Every boat has a name, like "Shmokin Joe," and some names only a skipper could spell—including "Scheherazade."

But behind every boat name is a story, and it's not always the story you'd expect.

"I think a lot of people assume that we partake, and we do not. It's just a fun name, that's it."

Some names just seem to fit in a fuzzylogical sort of way.

"It really applies to sailboat racing. There's some serious fuzzylogic that goes on with sailboat racing."

In the 116th Chicago Yacht Club Race to Mackinac, there are nearly 2,500 sailors from 49 states, 14 countries, and perhaps more than one planet.

"This is our mascot, Zorp."

They range in age from 14 to 88. They all set sail from Chicago to Michigan's Mackinac Island for different reasons.

"For us, it's a family thing. My son is on board. This will be his third Mackinac race. This will be my 27th. My dad did 47 Macks before he passed away, so you know, it's been in my family forever."

Victors will be crowned, but every voyager sails with a story.

"I believe every single boat has a good story, and if not, there's a good story in the future."

• Chicago