The TellTale April 2026

Sail Chicago Tell Tale
Issue 4: April 2026
Boatyard Open House Reminder

Do you want to learn more about the work our offseason maintenance teams do and possibly join? Or do you just want to see what the boats look like out of the water? Come find out! We want to remind you that we will be hosting a Boatyard Open House again this year at the Canal Street Marina. We’ll be giving tours, having a scavenger hunt, giving knot and equipment tutorials, and giving sneak peeks at our new maintenance tracking system. If you’re still looking for a volunteer role, we’ll be there to answer any questions you might have on joining maintenance. Coffee and doughnuts will be provided. 

Where: 2059 South Canal Street

When: Saturday April 11, 10–12

Volunteer for Maintenance

Sail Chicago’s maintenance program has continued work to get the boats ready for the coming season. We have openings for formal seasonal positions (winter, spring, summer, and fall) as well as general activities like boatyard work, mast steppings, and river trips. Maintenance is a fantastic way to learn about how sailboats work and no experience is required. Most positions are limited to a defined time frame and some can even be performed remotely! Maintenance volunteering has a direct impact on speeding up the start of the season! Check the volunteer section on My Sail Chicago for current postings, or join #colgate-maintenance-general on Slack to see when we're working in the yard. 

Additionally, a handful of volunteers are needed to serve as boat managers for the Colgates. The only formal requirement is Sail Chicago Skipper status and the willingness to lead a boat team. No experience with maintenance is needed since it’s a learning on the job role. 

If you have any questions or have interest, please contact James Wyeth and Ben Carls on Slack or by email (ben.carls@sailchicago.org, james.wyeth@sailchicago.org).

Class Registration has Begun

Students that signed up for the class registration lottery will be notified of their registration window no later than April 14. Please carefully read our Class Registration and Cancellation Policy for all the information you need to know about selecting classes and meeting our prerequisites.

Key Learn-to-Sail Upcoming Dates:

— General Registration Lottery closes to signups on April 10 at 11:59:59 pm
— General Registration opens with Group 3 on Wednesday, April 15 at 10:00 am
— General Registration continues through April or until classes fill
Remaining Learn-to-Sail seats will open to the public on Friday, May 1 at 10:00 am.

If you have never taken a class with Sail Chicago before, remember to sign up for the General Registration Lottery April 1-10. If you do not sign up by April 10, you will have to wait until May 1 to register for classes.

Bridge Season Coordinator Wanted

Sail Chicago’s maintenance program will include a few new positions this season. One that is actively being recruited for is Bridge Season Coordinator: a high-level leadership role (Level 4) overseeing river trips, mast steppings/unstepping, and commissioning / decommissioning. This position requires maintenance experience, and applicants should be comfortable with a minimum amount of hands-on boat time at the start of each season. That said, the role is primarily planning and coordination, and only active in spring and fall when boats move between the boatyard and harbors. No boatyard or in-season work is required. If you are interested, please send a note to James Wyeth (james.wyeth@sailchicago.org) and Ben Carls (ben.carls@sailchicago.org). A full job description can be found in the volunteer portal.

Volunteer Spotlight — Nina Wheeler

From the moment I joined Sail Chicago, I understood how special this club is. The affordable cost, the emphasis on breaking down traditional learn to sail barriers, the community, and the sheer volume of volunteers that it takes to make this club go 'round...it's like lightning in a bottle. In the beginning, I felt like a lucky beneficiary of this special club and I wanted — and still want — to give back.  

Why do you serve the organization, and what’s your current role?
I’m on the maintenance crew, and until recently I was the PSO Coordinator — after 4 years I am transitioning that role to another member. I am also a MCO Skipper.

What are you most excited about this upcoming sailing season?
I am excited to continue my skipper journey on the pathway to becoming an instructor. Since I am a skipper and MCO skipper, so this season I plan to become Tiller Time certified. I’m also excited to race this season and will continue to learn about the entire the fleet. 

What’s one surprising fact about you that most people don’t know? 
Outside of the sailing community, a fun fact is that I sail! Inside the sailing community, it would be that I am studying Spanish.

What is it about sailing that keeps you coming back?
I love volunteering in general and think community engagement is important. As for what keeps me coming back? Lake Michigan of course — who can get enough?

Social News

The next social event will be our annual Kickoff Party at Columbia Yacht Club where we will gather to reconnect, make new friends, and toast to the adventures on the water that await. Whether you're a longtime sailor or new to the sport, you are welcome to join. Stay tuned for the date and registration!

Annual Dues

Don't forget to pay your Sail Chicago annual dues if you have not done so already. Members must renew their dues before they can participate in member activities, including pre-season maintenance, river trips, and the Season Kickoff party in May. Thanks everyone for doing your part to keep Sail Chicago financially strong.

Merch for Sale

Check out our cool line up of Sail Chicago merch. T-shirts, polos, jackets, fleece, and hats from top quality vendors are all embroidered with our burgee logo. Take pride in Sail Chicago! Gift cards are available in increments of $25.00.

Buy Merch
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Shop for cool Sail Chicago Gear 
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View previous issues of The Telltale

Sail Chicago Mission Statement  |  Member Benefits  |  Fleet Locations  |  Member Log In  
Member Registration  |  Sail Chicago Rules and Regulations  |  Board Meeting Minutes
Instruction  |  Sailing Weather

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The TellTale March 2026