The TellTale June 2026

Jun 11

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!

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

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