Behind the Scenes of Yacht-A-Palooza: Our Grant Crowley Interview

We sat down with Grant Crowley, owner and manager of Crowley’s Yacht Yard, located at 3434 E. 95th Street on Chicago’s south side, to learn more about his fascinating journey and the upcoming event.

Grant’s love for the water began when he was a child, growing up near Belmont Harbor. By age eight, he was already displaying his entrepreneurial spirit, washing boats to earn pocket money. The high-rise buildings near the Harbor burned their trash in incinerators, and he found a steady summer income stream cleaning the soot from boats in the Harbor.

As a teenager, Grant’s ambition grew. He realized he could make more money cleaning racing boat hulls. He took the bus downtown to the library to check out the Navy Diving Manual. Yes, he learned scuba diving from a book he checked out for free and used his newfound skills to pay for college. When asked if he still dives, he chuckled, “I had my fill in college; it’s not something I ever wanted to do again!”

Grant’s connection to the water runs deep. His father, a Georgetown University graduate, worked as a lifeguard from 1937 to 1941 and later served as a lieutenant on the battleship West Virginia during World War II. Grant himself graduated from the University of Michigan with a degree in naval architecture and worked for a sailmaking firm before opening a boatyard in 1978.

Grant’s original boatyard, located on the south branch of the Chicago River between Halsted and Ashland, was the birthplace of “SAIL-A-PALOOZA,” the precursor to today’s Yacht-A-Palooza. Starting in 1992, he hosted this annual event, building a reputation for bringing the boating community together. In 2004, Crowley’s Yacht Yard moved to its current location, doubling its space from 12 to 24 acres, with significantly more indoor space.

So, what’s Grant’s favorite part of Yacht-A-Palooza? “The seminars,” he says enthusiastically. This year’s event promises an impressive lineup of speakers, including Captain Deborah Leja, guiding you in preparing for your USCG vessel inspection, David King speaking about the National Weather Service and Marine Preparedness, expert sailmaker Todd Basch, and many more!

We’re also excited to announce that Nautical Donations (nauticaldonations.org) will be open a day early for Yacht-A-Palooza! You can visit them on Friday and Saturday to donate or find gently used marine equipment and accessories. Nautical Donations is a wonderful organization that supports maritime education and youth sailing programs.

Our conversation with Grant was filled with fascinating stories and insights. The most surprising moment came when we asked him about his favorite boat. We expected a grand yacht, but his answer was simple and heartfelt: “The finest sailing vessel was a 23-foot Starboat I sailed as a kid. That was the best boat.”

This response perfectly encapsulates Grant’s passion for sailing and deep connection to the water. Yacht-A-Palooza is a testament to his dedication to the boating community, and we encourage everyone to join us on March 22, 2025, for a day of fun, learning, and camaraderie.

1.   Date: March 22, 2025

2.   Location: Crowley’s Yacht Yard, 3434 E. 95th Street

3.   Nautical Donations: Open on Friday, March 21, from 10-5 pm and Saturday,
     March 22, from 8-5 pm

4.   Check out the Yacht-A-Palooza website for a complete list of events & speakers