If you’ve ever sat on the shores of Lake Michigan and watched with envy as sailboats glide past, there’s an accessible way to make your dream come true.
“Many of the people who walk through our doors have never been on a boat before,” says Milwaukee Community Sailing Center executive director Holly Church. And since 1980, the center has been placing those maritime-curious people into boats and putting wind in their sails.

Tell us who you’d pick to be a Betty this year!
Membership is open to people of all ages ($437 individual, $731 couples) and comes with the opportunity to take classes on everything from the basics to spinnaker racing. Oh, and what else? Unlimited access to over 80 boats on McKinley Marina, weather training dependent, all summer long – from late April through October.
“We give people that opportunity to connect with the water,” Church says. “We don’t just teach you and drop you.”
If you’re new to sailing, you need to earn your light-air rating by completing a two-week fundamentals course ($288) – covering rigging, driving, tacking, gybing and more on a small Ensign sailboat. More important than the vocabulary is simply knowing where the wind is coming from and how to set your sails to compensate, says frequent sailor Bonnee Beth Lugauer.
While you’re joined by an instructor on your first week in the course, you and your crewmates can float by yourselves by the second week. Church says students often find themselves surprised that they learn so quickly.
Youth instructor Leo Madson says one of the first words prospective sailors learn is boom: the horizonal pole holding the bottom of the sail. Yelling the word serves as an onomatopoeic warning. “It swings very quickly from side to side,” he says. “It has a capacity to whack someone really hard.”
Leo Madson started sailing in 2022 through the center’s youth program for ages 12-17, and soon after began teaching the same program as an instructor. The 20-year-old always felt connected to the water, and says teaching lets him sail nearly every day of the week.
“I’m there to make sure everybody’s having a good time, and secondary to that is learning, growing their skill set and making friends,” he says. Madson helps guide members toward the experience they would enjoy most.
“If a person likes speed, adrenaline and danger-seeking, they can go out in heavier winds or a boat they’re less comfortable in,” he says. “And I have students that prefer the calm, contemplative sailing along a breezy, sunny afternoon.”
Seventy-nine-year-old Lugauer does it for the sense of accomplishment. “If it’s really windy, I just love it because I know I can handle it.”
MCSC has one cardinal rule: No one sails alone. Members can impress non-member friends and family by bringing them on board for $5 each. Otherwise, there’s always another member looking for a sailing buddy – whether they’re hanging out at the center or hitting up the group chat.
For Church, it’s important that everyone can access Lake Michigan, whether simply crossing a bucket-list item or discovering a lifelong hobby. For tense times, she says sailing offers a fresh respite on freshwater. “Personally, I push off that shore, and all of a sudden you’re disconnected from it all.”

