The TellTale May 2026

May 7

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

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.

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