"People are looking forward to being out on the water... to have that experience with their crew," said Martin Sandoval, chairman of the Chicago Race to Mackinac.
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What started in 1898 with just five boats has grown to several hundred. The 112th edition of the race brings together 240 boats and 2,100 sailors from around the world to compete in the 333-mile course up Lake Michigan. The event is the oldest annual freshwater distance race in the world.
"Last year was so difficult, it was just hard," said spectator Janet Holden.
Holden's husband is considered a Chicago Mac old goat because he's raced in 25 of the prestigious contests.
However, this year, the couple is cheering on their son.
"When he was racing with us, we were unbeatable. We were the fastest boat for our class," Chicago Mac racer Tom Barnes said.
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For the Oak Park native turned Dallas resident, this will be Barnes 18th Chicago Race to Mackinac Island, but it almost didn't happen after the vessel he was set to crew for was disqualified.
"I had flown here already. It would have been a bummer to sit on shore," Barnes said.
This year is Madeline Stauber's first time racing here.
"I'm so excited. I really like long-distance races and it's going to be a great time," she said.
The Chicago Yacht Club's race includes the Black Diamond, named because all on board are expert skiers. The craft hopes to place this year. Co-owner Craig Brown said the weather is good for racing, and this could be the year.
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"We're very excited. The whole crew has been preparing for this all year, talking about it all winter. We got a couple new sails we want to try out, and we're really looking forward to it," said Craig Brown, Michigan City, Ind. race participant.
Some of the crew on the Black Diamond have placed before. It is Tyler Marshall's 17th race in the annual event.
"You know, I always joke to the crew that this is at the top of my calendar. It's my week off to sail the Mac, don't touch money, don't touch phones, don't drive cars, just sail and be under the stars," Marshall said.
The race is about a 50 to 60-hour journey from Chicago's Navy Pier to Mackinac. It is a non-stop race, so sailors take turns with shifts, according to some sailors. The race requires strategy and taking wind into account.