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March 2026

Sail Chicago Tell Tale
Issue 3: March 2026
From the Editor:

It’s March! That means it is almost time to sail. Ok, almost, almost. But now is a great time to plan your Sail Chicago participation! So consider signing up for maintenance, visiting the boatyard, and meeting some new sailing buddies at Sail Chicago’s first 2026 social event. Stay warm and see you on the water..soon…

Meighan Depke, Editor

Boatyard Open House

Interested in learning more about offseason maintenance? Or maybe just to see what the boats look like out of the water? Come find out! Join the maintenance teams at the Boatyard Open House at the Canal Street Marina. The teams will be giving tours, holding knot demonstrations, and allowing sneak peeks of Sail Chicago’s new maintenance tracking system. Coffee and snacks will be provided. 

Where: 2059 South Canal Street 

When: Saturday April 11, 10–12

Class Registration Begins in April

A new season of sailing is almost here, and it begins with the rollout of our schedule of classes! New and returning students can find information about the class rollout and registration timeline on the Sail Chicago website. Our class schedule will post the last week in March. Lottery signups will open on April 1, and individuals in the 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 Dates for 2026 Learn-to-Sail Course Rollout:

General Registration Lottery opens for signups, April 1
— Group 1 Pre-Registration begins April 1 at 10:00 am
— Group 2 Pre-Registration begins April 5 at 10:00 am
— 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.

From the Volunteer Team

Hello Sail Chicago! Volunteer reporting for 2025 is complete, service time is set, and status is updated on member landing pages when logged into my.sailchicago.org. Sailing credits for those in leadership and management positions will be added by the end of March.

Looking ahead, there are many opportunities for service time in 2026 that take advantage of skills you already have, or teach you something new. Our volunteer site shows all positions available for 2026. If you indicated an interest in continuing in your 2025 role, you've probably been re-assigned to that position. Please check the data hub for your current assignments.

NEW IN 2026: VOLUNTEER LEVELS!

To help guide volunteer positions that best suit skills and experience, the Volunteer Team has developed levels for each position. The volunteer site now lists all the available opportunities in order by level. Here's what those levels mean:

Level 1 — New to Sail Chicago: For new members and those looking for an entry-level commitment. No skills or experience are neededl; these are show up and help positions. Experienced members will be available for guidance. Many of these “jobs” will place members on a mailing list for opportunities that open as needed. Examples: River trips, boat teams, mast stepping, social

Level 2 — Some Experience Required: These positions require a year of membership to Sail Chicago or specific skills that are needed for the organization. Any job that requires a skipper is at least level 2. Examples: Deputy boat managers, deputy maintenance team leads, some IT jobs, MCO Skipper, Tiller Time Skippers

Level 3 — Skilled or Oversight Positions: These positions require 2 years of membership and may require specialized skills or a license/credential and may include direction of other members. Positions frequently involve deadline oriented tasks that ensure the organization operates smoothly. Examples: Higher-skill IT jobs, bookkeepers, instructors, boat managers

Level 4 — Program Directors: These members lead our programming. Examples: Licensing and insurance coordinator, lead instructor, social director, IT director

Level 5 — Board of Directors and Officers

Remember, if you fail to meet your 2026 service time requirement, either because you didn’t volunteer for a position or you failed to fulfill the responsibilities of the position, you will be required to pay a service time waiver for the 2026 season before you can renew your membership in 2027.

There are plenty of volunteer opportunities available each season, and many of them can be carried out in just a few hours each month. If you're not sure where to start or what you'd like to do, reach out to the volunteer team at volunteer@sailchicago.org.

Maintenance Volunteers Wanted

Sail Chicago’s maintenance program has already begun work for the season and is looking for volunteers! Openings include formal seasonal positions (winter, spring, summer, and fall) as well as general activities like boatyard work, mast stepping, and river trips. Maintenance is a fantastic way to learn about the boats and no experience is required. Most positions are limited to a defined time frame and some can even be performed remotely! Check the Volunteer section on My Sail Chicago for current postings, or join #colgate-maintenance-general on Slack to see when teams are working in the yard.

If you have any questions don’t hesitate to reach out to James Wyeth and Ben Carls on Slack or by email at ben.carls@sailchicago.org /james.wyeth@sailchicago.org

Bridge Season Coordinator Wanted

Sail Chicago’s maintenance program has a few new positions this season and one for which we are actively recruiting is Bridge Season Coordinator. This high-level leadership role will oversee river trips, mast stepping/unstepping, and commissioning/decommissioning. This position requires maintenance experience and applicants should be comfortable with some hands-on boat time at the start of each season. 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 contact james.wyeth@sailchicago.org and ben.carls@sailchicago.org. A full job description can be found on the volunteer portal.

Social News

Our first social event of the year is only a week away. Meet us at Big Mini Putt Club Lakeview for an exciting pre-sailing season activity! Dust off your skills and kick things off with a mini golf event you won’t want to miss.

When: Thursday, March 12, 6–8 PM

Where: Big Mini Putt Club, 3655 N. Halsted St.

Who: Free for Sail Chicago members

Registration is required and spots are limited. Your registration includes two hours of unlimited mini golf. Drinks will be available for purchase.

Register here

In Memoriam – Jay Owens

On Sunday, February 8, Jay Owens passed away peacefully in his Colorado home, surrounded by friends and family. He died from complications that arose from acute leukemia.

Old timers in Sail Chicago will remember Jay as a founding member of Sail Chicago. He was elected to its first Board, where he served for several years. He also served as the organization’s bookkeeper for well over fifteen years and was a member of the Cruising Program’s maintenance team. He liked nothing better than going out on weekly maintenance sails on Sail Chicago’s first cruising boat, Emotional Rescue, and later on Priorities. He will be missed.

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
Contact Us
Shop for cool Sail Chicago Gear 
Follow us on Facebook for updates, reminders, event info and activities!
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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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
Contact Us
Shop for cool Sail Chicago Gear 
Follow us on Facebook for updates, reminders, event info and activities!
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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May 2026

Sail Chicago Tell Tale
Issue 5: May 2026

Colgate Class Rollout Update 

The 2026 Sail Chicago Colgate class calendar is finalized! This year, three dozen instructors will teach 40 courses — 17 Crew, 11 First Mate, and 12 Skipper Prep. The complex task of matching instructor availability with boats and students was accomplished using new software developed by member Alan Street. The lottery was coordinated by Gerry Stacy and executed on the IT platform managed by Suhail Ansari. Thanks to all three for this impressive achievement!

Course registration opened to the public on May 1 via the website.

We are pleased to welcome several new volunteers to the instruction team: Kevin Micks (survey administrator), Connie Breuer and Melissa Locke (instruction program documentation and design), and Andy Rostad (BKI coordination). A US Sailing liaison position remains open.

The kick-off instructors meeting will be held on May 9 from 10AM–12PM at the Humboldt Park Branch of the Chicago Public Library. Here's to a great summer on the water!

Take Your Sailing to the Next Level

The Sail Chicago Racing Program is designed for sailors who want to continue learning through hands-on experience, teamwork, and healthy competition.

Racing is an extension of Sail Chicago's instructional mission, going beyond what is taught in our classes. Participants will learn advanced skills like spinnaker handling, close-quarters maneuvering, and racing rules. Every race is an opportunity to grow as a sailor. Expect a culture of accountability, respect, and plenty of post-race camaraderie.

Requirements: Sailors must have completed a Crew Class. You can join at any time during the season!

Registration: Sign up on the Sail Chicago website by purchasing a racing season ticket. The $100 fee covers all Wednesday night races and unlimited racing tiller time.

Stay Connected: Join #racing on Slack to stay up to date with news, alerts, tactical tips, and chalk talks. Slack is the hub to connect with fellow racers and build camaraderie.

Social News

Sailing season is here! Join us for the annual Sail Chicago Season Kickoff Event — a great opportunity to meet and reconnect with fellow members and guests. All members and students are welcome, and each may bring one guest at no charge. Snacks and refreshments will be provided.

 

When: Saturday, May 16, 2026 | 3 – 6PM

Where: Columbia Yacht Club, 11 N Jean Baptiste Pointe du Sable Lake Shore Dr.

Who: Free for registered Sail Chicago members +1 guest

Register here

Get Involved with the Social Committee!

tnterested in helping bring Sail Chicago's member events to life? The Social Committee is looking for enthusiastic volunteers! To learn more or get involved, connect with Kahla and Salman at the Kickoff Event on Saturday, May 16, or reach out anytime on Slack.

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 mast steppings, river trips, and boat managers. 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. 

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).

Become a Tiller Time Skipper!

Sail Chicago is seeking skippers for its 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 more quickly and advance to skipper status. Tiller Time skippers play a vital role in this process.

There are several advantages to becoming a Tiller Time skipper:

  • Sharing your love of sailing with committed and enthusiastic students
  • Spending more time on the water without scheduling a private sail
  • Making new friends and sailing buddies
  • Helping you decide if you'd like to become an instructor
  • Fulfilling your annual service requirement by completing five Tiller Times as a skipper

If you're interested in becoming a Tiller Time skipper — whether to participate in an actual Tiller Time or simply to learn more — contact Steve VanderVoort at tillertime@sailchicago.org.

2026 Basic Cruising

The full lineup of Basic Cruising classes is now available on the website. Classes are open to all Basic Keelboat Skippers. As you review the schedule, keep the following in mind:

  • Two-course structure: We offer both First Mate and Skipper Prep classes. Now in our second year, the program is designed to meet you at your current level and support a clear, accessible progression.
  • US Sailing alignment: With more instructors completing the US Sailing Cruising Instructor (CI) certification, we're bringing greater consistency and depth to our cruising program.
  • Current cruising skippers: We encourage all current cruising skippers to register for Skipper Prep this season as we continue building skills and confidence across the program.

Please review the Class Registration and Cancellation Policy before registering. For questions, contact the instruction team at learning@sailchicago.org. We look forward to another great season on the water!

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
Contact Us
Shop for cool Sail Chicago Gear 
Follow us on Facebook for updates, reminders, event info and activities!
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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June 2026

Sail Chicago Tell Tale
Issue 6: June 2026
At last it is summer and we can all do what we love — sail! There are plenty of other things going on as well, from ongoing maintenance to fun off the water at social events. Need a service job? There are plenty of openings for maintenance, IT, social and more. Looking for a sailing buddy? Be sure to check out "share a sail" on slack. All you have to say is "hey who wants to go sailing?' and a new friend will find you. So get out there and sharpen your skills, learn new ones or help a newbie practice.
– Meighan Depke, Telltale Editor

Maintenance Update 

As of today, four Colgates are in the harbor and getting plenty of use by members. Thanks to everyone who helped with the river trip! The rest are on their way — the maintenance crew is currently focused on ensuring everything is in place for our boat teams to run smoothly. Keep an eye on Slack for minor updates to the tracking and reporting of boat issues.

We are also still looking for in-season volunteers! Boat team members are always welcome, and positions for boat manager and deputy are still open. If you're interested in leading a small team to take a boat out every other week to inspect and address issues, this role is for you. Contact James Wyeth or Ben Carls on Slack if you're interested.

Social News

June Happy Hour
Interested in learning more about Sail Chicago’s racing program? Come meet members of our racing team, explore racing opportunities, and socialize with the rest of the Sail Chicago crew over drinks at one of Chicago’s best waterfront venues! All members and students are welcome.

When: Tuesday, June 30th | 5:30–7:30 PM
Where: Island Party Hut, 355 Chicago Riverwalk
Who: Members and students +1 guest

Includes 1 drink ticket per person and Light Snacks. We hope to see you there!

Register here

Become a Tiller Time Skipper!

Sail Chicago is seeking skippers for its 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 more quickly and advance to skipper status. Tiller Time skippers play a vital role in this process.

There are several advantages to becoming a Tiller Time skipper:

  • Sharing your love of sailing with committed and enthusiastic students
  • Spending more time on the water without scheduling a private sail
  • Making new friends and sailing buddies
  • Helping you decide if you'd like to become an instructor
  • Fulfilling your annual service requirement by completing five Tiller Times as a skipper

If you're interested in becoming a Tiller Time skipper — whether to participate in an actual Tiller Time or simply to learn more — contact Steve VanderVoort at tillertime@sailchicago.org.

Rhodes 19 Orientations

Expand your sailing résumé by becoming a Rhodes skipper. If you've never sailed a Rhodes, now is the time! Smaller than the Colgates and sitting lower in the water, they're a lively ride you can really feel.
Orientations are open to any Colgate skipper. We have open seats on June 10th and 26th, with more sessions coming in July, August, and September. Sign up on the Course Availability page at my.sailchicago.org.

Ideal 18s Information

The Ideals are now being prepped for the season. If you're not familiar with the Ideal 18s, they are the smallest boats in Sail Chicago's fleet — just 18 feet long, with a narrower hull than our other boats. This makes them sporty and fun to handle. You'll sail close to the water and might even get a little wet depending on conditions, but their heavy fixed keel keeps them stable so you can heel them without any fear of capsizing.

Their size and self-tacking jib make them perfect for sailors looking to learn to single-hand a boat. A great way to get familiar with them is to join the maintenance team. If you'd like to learn more, or if you're already a skipper and want to get checked out on the Ideals, reach out to Ken Pinkus or Stefan Loebling on Slack.

Service Updates

In case you missed the recent announcement, Sail Chicago has updated its policies, processes, and IT systems for 2026 to make it easier and more rewarding for members to contribute to the organization's success.

All members are now required to contribute a minimum of 25 service hours — up from 20 — to remain in good standing. Starting this year, members can also earn boat rental credits based on the hours they contribute and the role they fulfill.

Read the full details 

Member Dashboard

Sail Chicago now has member service dashboards to track your contribution roles, find new ways to get involved, review your signups, and log hours throughout the year — no more scrambling at year-end to remember what you did! You can report hours on your assignments anytime. Watch for an email from the Member Service team with a link to your personal dashboard.

2026 Season Kickoff Event Recap

Thank you to everyone who attended the Sail Chicago 2026 Season Kickoff Event on Saturday, May 16, at Columbia Yacht Club! We had an incredible turnout with 120 attendees — our largest event to date!

A special thank-you to everyone who helped make the event possible, including our social directors, program speakers, the Calypso crew, and the Columbia Yacht Club staff and volunteers.

What makes Sail Chicago special is our service teams — they make the organization and its outstanding instructional programs possible. Service is also one of the best ways to meet fellow members, develop new skills, and become more involved in the Sail Chicago community. Our Service Coordinators highlighted some of the opportunities discussed at the event:

Maintenance: Ben Carls shared information about maintenance and the opportunities to join the maintenance crew or a boat team. It’s a great way to learn more about the fleet, gain hands-on experience, and enjoy maintenance sails throughout the season.

IT & Administration: Suhail Ansari shared the many ways the IT Committee supports Sail Chicago and its programs. The team is always looking for engaged volunteers —members with an interest in technology or experience in IT are encouraged to get involved and help support Sail Chicago's technology infrastructure and operations.

Racing: Tom Hafner introduced members to Sail Chicago's Wednesday evening racing program. Racing is a fantastic opportunity to get on the water, develop new skills, and meet fellow sailors. No racing experience is required — everyone from beginners to experienced racers is welcome.

Instruction & Tiller Times: Dan Hazlett shared details about instruction — the heart of Sail Chicago. The instructors who lead classes and host Tiller Times create the learning opportunities that help our members grow. He noted how serving as an instructor or skipper is both rewarding and an great way to improve your sailing skills while giving back to the community.

Social Committee: Kahla Graham and Salman Ali shared an exciting lineup of events planned for the 2026 season. Interested in helping organize events, meeting fellow members, or sharing ideas for future activities? Join the Social Committee! 

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
Contact Us
Shop for cool Sail Chicago Gear 
Follow us on Facebook for updates, reminders, event info and activities!
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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