Another day on the water results in a balloon rescue by the Telltale team! Editor Emeritus Steve Vandervoort and his daughter Lise joined Editors Anders Carlson and Meighan Depke to tackle some September wind. Our boats are still int he water, so enjoy September, and rescue some balloons! Hope to see you all at our last Happy Hour of the season, Sept 18 at Island Party Hut! — 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:
— Complete the 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! Applications and nominations must be submitted by Sunday, October 5, 2025 to qualify for the election.
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Single-handed Sailing Returns
The On-the-Water committee has worked with the Rhodes and Ideals skippers to establish new guidelines for single-handing and additional equipment has been purchased for the Rhodes to ensure that skippers will be able to return to the boat should they fall out.
With these updates to our rules and systems, the board has authorized the resumption of single-handed sailing, effective immediately.
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Make-up Skipper Check-outs
For those who received a Plan of Improvement (PoI) during Skipper Check-outs, don’t be discouraged. Keep sailing, connect with other skippers, take advantage of Tiller Times and continue to build your confidence and refine your skills. The season is not over yet! Make-up Check-outs are available on:
Saturday, September 27th and Wednesday, October 1st.
If these dates don’t work for you, please reach out to your instructor or email us at leadinstructor@sailchicago.org to explore other options.
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Volunteers Still Needed
It's starting to feel like the end of the sailing season is just around the corner. But our volunteering season doesn't end when sailing does! Do you still need to meet your service time for 2025? Are you looking for additional hours? Below are some end-of-season opportunities to help out before our volunteering season ends on December 31.
Help unstep Colgate masts and transport boats to the boatyard in October. Unstepping the masts takes several hours on a Saturday or Sunday and many hands are needed but no experience is required. Come see how we lower a mast! After lowering the masts, the Colgates are taken down river to the Canal Street boatyard. Crews are needed to make the two-hour trip on weekday mornings.
Help get our boats ready for the winter. Once we get the boats to the yard, there's work to be done to safely store them for the winter months.
Social Committee volunteers are needed to help with upcoming events. Extra hands are needed to help with the end-of-season dinner on Thursday, October 23.
Help solicit business donations for Sail Chicago's upcoming auction. This is an easy way to volunteer...just tap into your existing network and business favorites. Many businesses see auctions as a great way to get new bodies through their door and are happy to give a coupon or free service.
To sign up for any of these opportunities, complete the Volunteer Signup Form or contact the Volunteer Team at volunteer@sailchicago.org.
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 Social News
Happy Hour & New Skipper Celebration
Thursday, September 18
Island Party Hut
355 Chicago Riverwalk
6:00pm – 8:00pm
Join Sail Chicago for its last happy hour of the season at Island Party Hut! We will celebrate our new skippers, soak up the riverfront vibes, and close out summer with drinks, great company, and plenty of appetizers. First drink is on us, so come raise a glass and send the season off in style!
Congrats to our newest class of sailors who have successfully completed their On-the-Water Skipper Check-out! As many of us know, it is an incredibly rigorous and thorough process that ensures every skipper at Sail Chicago meets the highest standards of safety and seamanship.
Abigail Anderson, Suhail Ansari, Todd Barton, John Dufford, Michael Ford, Albert Guralnik, Sergey Ilin, Chris Kelly, Brandon Larue, Jessica Limardo, Dan Lesser, Tyler Monce, Jack McGrane, John Novembre, Rachel Park, Chris Schramm, Brooke Schmidt, Claire Walsdorf, Nina Wheeler. Let’s celebrate these sailors’ hard-earned accomplishment!
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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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Community Cruising Series: Member-Only Sails!
Sail Chicago’s Community (DEI) Committee is thrilled to kick off our brand-new Community Cruising Series this September! These special Sunday afternoon sails are all about celebrating our members and creating welcoming spaces on the water.
Here’s what’s coming up:
— Women on the Water: Sun, Sept 14, 1:00pm
— BIPOC Sail: Sun, Sept 21, 1:00pm
— LGBTQIA+ Sail: Sun, Sept 28, 1:00pm
Each cruise will be held on our Colgates, and seats are limited, so don’t wait! To sign up, simply log in to the SAIL Chicago website and head to Reservations > Seat Availability > Listed Under Cruises.
The cruises will become visible two weeks prior to the event. If you’d like to be the skipper of record for one of these exciting sails, please send a DM to Shawn of the Lake on Slack. Skippers can choose their own first mate.
Come join the fun, connect with fellow members, and let’s make waves together!
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Have you ever wondered about what the fireworks look like from the water? Thanks to Art Witkiewicz for sharing this amazing photo taken from Blue Fish, one of Sail Chicago’s Rhodes.
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Racing News
Sadly, another sailing season is drawing to a close. But fear not, we will keep racing til they rip the last Colgate out of our dead-cold hands. Starting September 3, we will transition from our standard windward/leeward format to old school crib races. I hear there are folks who prefer this! I love diversity, in all its varied forms.
Join us as we have fun and learn. Speaking of which, so far this year we have two new foredeck specialists and one new racing skipper. If you want to get in on that action, drop us a line anytime. We're here to make that happen.
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Notes from the Dock
Best practices to help keep our fleet and facilities running smoothly:
Check Fleet Status Before Sailing: 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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In Memory of Jack Shubat
The maintenance crew of Priorities is saddened to pass along news of the recent passing of our long-time crew member Jacob (Jack) Shubat.
Jack passed away on July 25 in the care of his family in the St. Louis area following a brief illness. A retired mechanic with United Airlines, Jack brought his skills to the care of the engines on the cruisers Priorities and Emotional Rescue.
Sail Chicago members wishing to pass condolences to the family may do so by contacting Kenn Sinko, whose email address is listed in the Sail Chicago member directory.
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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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