"This is super exciting," said John Desmond, a sailor in the race. "I don't think there's a lot of places in the world where you can have this kind of a view of the city."
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230 boats are traveling well over 300 miles to Michigan's Mackinac Island in Lake Huron.
This year is the 114th running of the famed regatta, known by many as 'the Mac.'
"When you leave, you always look at the skyline to see how far away you're getting," said Michael Schultes, a sailor in the race. "And when it's gone, you say my goodness, we're in the race."
2,100 sailors from around the world and across the country set sail.
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"Year-after-year, I keep saying, this is the last one, but I keep coming back," said Jamal Alwattar, a sailor in the race. "It's really challenging. It's an endurance race."
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This year is Alwattar's 31st time in the regatta.
Boat crews range in size from just two members to as many as 22 people, depending on the size of the boat.
"There is a lot more communication going on, as opposed to just like two people, you have to talk to everybody so everybody understands what's going on," said Luci Ramirez, a sailor in the race.
For 15-year-old Ramirez and 16-year-old Lauren Gullo, this is their first time in 'the Mac,' and they were eager to get sailing.
"I'm very excited about getting there and celebrating with my family once I get there," Gullo said.