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Yachtapalooza Sets Sail This Weekend, Aiming To Get South Siders Excited About Boating

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EAST SIDE — A day-long open house for local boaters of all experience levels this weekend in East Side aims to be an accessible, fun draw for newbies to the nautical world, organizers said.

Yachtapalooza takes place 8 a.m.-4 p.m. Saturday at Crowley’s Yacht Yard , 3434 E. 95th St.

The free, indoor event celebrates its 25th anniversary this year. It features free seminars and demonstrations, a pig roast, live music, a flea market Friday and Saturday and a three-day sale on nautical items from Boater’s Closet Friday-Sunday.

Organizers hope to draw 1,000 current and future mariners out to this year’s event, said Nick Fugate, sales manager at Crowley’s Yacht Yard.

Yachtapalooza will also include a boat showcase by Nautical Donations , Crowley’s charitable arm, featuring several rehabbed, budget-friendly boats for sale.

Proceeds from the boat sales will support nonprofits like the Chicago Maritime Society and the Judd Goldman Adaptive Sailing Foundation, Fugate said.

The Chicago Boat Show dropped its sailing portion in recent years and is planning a move to the suburbs next year , so this weekend “is probably the closest thing to a sailboat show that we’ve got in Chicago,” said Charles Szymanski, a Yachtapalooza organizer and president of the nonprofit Rainbow Races .

With a few dozen vendors and free seminars on topics like marine pumps and toilets, splicing line and rope, and applying epoxy and varnish, Yachtapalooza offers “anything you would need” to maintain a boat, Fugate said.

The seminars give attendees “the chance to use the products, put their hands on them and feel them, and learn a little more than watching a powerpoint on a screen,” he said.

The event is “the perfect opportunity for anyone looking to get into sailing, [with] questions about sailing or [wanting] to check out a sailboat for the first time,” Szymanski said.

Rainbow Races is one of Yachtapalooza’s featured vendors, and its members will host one of the day’s seminars. The group aims to erase barriers marginalized groups may face in getting into sailing, Szymanski said.

It’s the only U.S. Sailing-sanctioned, LGBTQ+ sailing school in the country, and the only LGBTQ+ sailing organization in the Midwest, he said.

Rainbow Races’ first day of sailing school begins May 18. The group is offering a $50 early-bird discount on sailing classes through the end of April with the discount code “hydra50.” To register, click here .

The sailing world struggles with homophobia, misogyny, elitism and other forms of discrimination prevalent in other sports, Szymanski said. Rainbow Races creates a safe community around the sport which tries to counter those problems, he said.

Despite its issues, due to the collaborative nature of sailing, it’s also “probably the most friendly sports arena I’ve experienced,” Szymanski said.

“Sailing is a true team sport,” he said. “You have to trust your crewmates with your life, and you also have to support each other.

“Sailors are aware if we don’t evolve, we die … If the wind changes, you have to change with it.”

Chicago’s sailing community is robust, particularly with groups like the Park District, local yacht clubs and Rainbow Races encouraging new people to explore the sport, Fugate said.

But with a massive lake as Chicago’s backyard and “a very strong maritime history” in the city, the community could definitely stand to grow, Szymanski said.

Yachtapalooza is a free “casual meeting of the minds” that can help spread the joy of sailing and boating and change a misperception that the community is only for the ultra-rich, Szymanski said.

Million-dollar yachts “are great to look at and to dream about, but when you get down to it, Chicago is a blue-collar city,” Szymanski said. “A lot of the folks trying to buy boats are probably younger and more [budget-conscious]. It makes this a really unique opportunity to bring people in, in a very casual, unencumbered way.”

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Maxwell Evans

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773-221-9990

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Crowley's operates a well stocked and well staffed ship's store that ranks amongst the finest ship's chandleries in the country. The store stocks everything you need to maintain and upgrade your boat. We have an extensive selection of engine parts, rigging, repair and maintenance supplies and soft goods. We are dealers for a wide variety of products and can source just about anything for your boat. Stop in and talk to our staff and let them help you plan your next project. Crowley's also operates The Boater's Closet. An online store specializing in the very best in marine apparel and accessories.

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Crowley's Yacht Yard Lakeside

3434 East 95th Street, Chicago, Illinois 60617, United States

773 221-9990

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Take Lake Shore Drive / South Shore Drive (Rt. 41) south to 95th Street.
Turn right, go west on 95th St. approximately 200 yards to boatyard entrance on the left, just before bridge.
Take the Kennedy Expressway (I-90) through downtown Chicago. I-90 becomes the Dan Ryan Expressway.
Enter the Chicago Skyway toll road at 63rd Street. (Skyway entrance is on the left from the local lanes only.)
Follow the Skyway to 92nd Street, exit on the right.
Turn left onto 92nd Street. Go east to S. South Chicago Avenue.
Turn right on S. South Chicago Avenue. Go southeast to 95th Street.
Turn left on 95th Street (Rt. 12/20). Go east approximately 300 yards to boatyard entrance on the right, just after bridge.
Take I-57 to Halsted Street exit.
Left on Halsted Street, go north to 95th Street (Rt. 12/20).
Turn right on 95th Street, and go east.
Boatyard entrance is on the right just past the bridge over the Calumet river.
Exit I-94 at S. Stony Island.
Follow the long exit ramp north to 95th Street (Rt. 12/20).
Turn right on 95th Street, and go east for approximately 4 1/2 miles.
Exit Indiana Toll Road at Indianapolis Blvd. (last Indiana exit).
Follow Indianapolis Blvd. northwest to Ewing Ave. (Rt. 41).
Turn right on Ewing Ave. Go north on Ewing Ave. to 95th Street (Rt. 12/20).
Turn left on 95th Street. Go east approximately 200 yards to boatyard entrance on the left, just before the Calumet River bridge.
The downtown station is located on Michigan Avenue between South Water Street and Randolph Street, two blocks east of the CTA Orange, Green and Brown lines on Wabash Ave. Click here to see a map of this area.
Take the Metra Electric to the 93rd Street station. Click here for a schedule.
Click here to see a map of the entire Metra Electric route.
From the 93rd Street Station, walk west on 93rd Street 1/2 block to Baltimore Ave.
Go left (south) on Baltimore, walk 1 block to South Chicago Avenue.
Go left (southeast) on South Chicago Ave., walk 2 blocks to 95th Street (Rt. 12/20).
Go left on 95th St. Walk across the bridge to the yard entrance on the right.
Note: Metra now allows bikes on trains with some exceptions. See Metra's Bike Rules Page for more information.
If you plan to arrive by water, you can view a nautical chart (for reference only).