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Summer is in full swing, and this Telltale shows it! Valuable tips are below, along with social events open for registration. We hope to see everyone at Belmont Yacht Club for the Friends and Family picnic. If you haven't been inside, it's a fun place to hang out in a fantastic setting. If you aren't sailing enough, get on the "share-a-sail" slack channel and don't be shy! Create a post and head out on the water! — Meighan Depke, Editor
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Run for the Board!
Would you like to take a turn on the tiller that steers our organization? Do you have ideas that you know will make Sail Chicago better? Do you think there's a point of view missing in our leadership, and that's yours? Then run for the Board!
Board membership is open to all Sail Chicago members in good standing, and we encourage everyone that wants to run for a board seat to do so. We have seven seats coming open, and anyone is welcome to run.
If you are interested in running, here's how to do it.
— Complete this candidate application form.
— Have another returning member complete this nomination form.
Nominating members must have been a Sail Chicago member for at least 12 months. Multiple people can nominate you, but only one is needed.
That's all there is to it! All applications and nominations must be submitted by Sunday, October 5, 2025 to qualify for the election.
If you are curious about what it's like to serve on the board, come talk to us! We'll be holding a Meet the Board event on August 21 from 6-8pm at the Weather Mark Tavern.
— Gerry Stacy, Board Chair
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Become a Tiller Time Skipper!
We’re seeking skippers for Sail Chicago’s Tiller Time program. The program’s mission is to provide meaningful practice for current students outside of the regular class structure, allowing them to improve their sailing skills and advance to skipper status. As a Tiller Time skipper, you become a vital link in this process. There are several advantages to being a Tiller Time skipper. They include:
— Sharing your love of sailing with committed and enthusiastic students
— Spending more time on the water without having to schedule a private sail
— Making new friends and sailing buddies
— Helping you decide if you’d like to become an instructor
— Completing five Tiller Times as a skipper fulfills your annual service requirement
To learn more and to find out if you’re eligible to become a Tiller Time skipper, contact Steve VanderVoort at tillertime@sailchicago.org.
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Priorities Wins Second Place at Lighted Boat Parade
Thanks to everyone who helped Sail Chicago participate in the 2025 Boat Parade on July 12 in Monroe Harbor. The creativity and teamwork that day helped Sail Chicago win second place and $1500 that will be used to help pay for next summer's Priorities boat slip. Whether you assisted with the planning and logistics, decorating of the boat, music and costumes, or simply showed up with enthusiasm to cheer us on—your role was vital. It was inspiring to see such teamwork, reflecting the very best of what our Sail Chicago organization can accomplish together!
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 Social News
Annual Picnic Recap
Thanks to everyone who made it out to the Belmont Yacht Club for our annual picnic! Even though the weather didn’t cooperate for our short sails, we still had an awesome turnout and an even better lunch. Always so fun to spend time together—rain or shine!
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August Happy Hour
Thursday, August 21, 6-8pm
We’re heading back to the Weather Mark Tavern, 1503 S Michigan Avenue, for our August happy hour. First drink is on the house for you and a guest! Hope to see you there.
End of Year Dinner, October 23rd
Celebrate the end of sailing season at Columbia Yacht Club! This event will directly follow the Annual Membership Meeting. Details and signup to come.
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Notes from the Dock
Best practices to help keep our fleet and facilities running smoothly:
Check Fleet Status Before Sailing: Skippers Before heading out, all skippers should log into the Sail Chicago website to check the fleet status. This real-time report includes updates from skippers who sailed before you. It’s the best way to stay informed about any issues—or whether a boat might be out of commission—so you can plan accordingly or switch boats if needed.
Parking Pass Accountability: Skippers are responsible for the parking passes they use or lend to their crew. Always track by noting when a pass is taken and returned. If a pass goes missing or you notice a recurring issue, please DM “Shawn of the Lake” via Slack.
Monroe Trailer Visit Log: Please record all visits to the trailer in the logbook on the aft wall. Note the purpose of your stop and any items/parts taken. This helps manage inventory and track usage. And just like our boats, let’s keep the trailer clean and organized. Please take a moment to tidy up before you leave.
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Sail Chicago Supports PALS on the Water
On July 31st, Sail Chicago proudly joined forces with neighboring organizations—Chicago Yacht Club Foundation, Columbia Yacht Club Sailing School, and Chicago Harbors/Westrec—to welcome participants of the PALS program (palsprograms.org/chicago) aboard for short sailing trips around Monroe Harbor. While strong winds kept us close to shore, the spirit of the day soared high.
PALS is an inspiring nonprofit that designs summer programs pairing individuals with and without Down syndrome in one-to-one friendships. Participants came from across the country—and even internationally, including a young woman from London—to spend a week exploring Chicago. Sail Chicago contributed volunteers as skippers and first mates, helping to bring the joy of sailing to all.
This event was more than just a sailing experience. It was a meaningful exchange between people from all walks of life. One participant shared that photos from the sail would be part of his “Congratulations Project” letter—an initiative where individuals with Down syndrome write heartfelt letters to new or expecting parents of a child with the same diagnosis. As PALS puts it, these letters aim to “inspire, encourage, welcome, and most importantly, congratulate new families.”
A big shoutout to Shawn Joseph for helping coordinate Sail Chicago’s involvement. The cross-club collaboration added to the camaraderie—we had Chicago Yacht Club sailors aboard Columbia Yacht Club Colgates with Sail Chicago volunteer skippers all working together.
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Experienced Sailors Accelerated Process
Sail Chicago welcomes everyone to our membership and a large part of our organizational focus is to introduce people to sailing and teach them how to be outstanding sailors. But Sail Chicago also welcomes experienced sailors! We insist that each new member go through our Skipper qualification process by taking our Skipper Prep class. This ensures that all members are well-acquainted with our boats, our procedures, and become properly oriented to Monroe Harbor.
However in rare cases, this requirement may be abbreviated for an individual upon the recommendation of the Instruction Team. You can review our Skippering Exception Process to learn more.
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Racing News
The Verve inshore is set for August 23 and 24, at Belmont Harbor. It's two days of racing, and a big party Saturday night at CYC Belmont. All boats should have experienced racing skippers. Feel free to register at vervecup.com/inshore or email tom.hafner@sailchicago.org to be added to my list of people looking for boats and boats looking for people.
Finally, join Wednesday night racing. The best value on the lake gets you unlimited Wednesday night races, unlimited Racing Tiller Times, and access to special events for $100. Ever wonder what it's like to be at the helm, run the foredeck, or set strategy for the starting line? You get to try out every position while expanding your skill set. Newbies welcome so come out and have fun with us. (You must have completed an SC crew class.)
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Merch for Sale
Check out our cool line up of Sail Chicago merch. We’ve sourced T-shirts, polos, jackets, fleece, and hats from top quality vendors, all embroidered with our burgee logo. Take pride in Sail Chicago and wear your merch at social events and on the water. Gift cards are available in increments of $25.00.
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