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Sailing season is upon us, and with the boats heading to the harbor, now is the time to dust off your sailing gear. Six of eight Colgates are now on their mooring cans in Monroe Harbor, waiting to be rigged. Weather continues to slow progress but we are getting there!
— Meighan Depke, Editor
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Pre-Sail Orientation
With sailing classes about to begin, a reminder — before attending the first class, new students are required to attend a Pre-Sail Orientation (PSO). This is an opportunity to learn about Sail Chicago as an organization, find out what is expected for class, meet some seasoned members of the club, and ask questions. Sign up for a PSO on the my.sailchicago.org portal under Instruction > Course Availability. The 90-minute course is available in-person or virtual, so find a date and time that works for you. For questions, please email our PSO Coordinator, Nina Wheeler, at pso@sailchicago.org.
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Waitlist for Classes
Registration for the 2025 season is complete and all classes are full. If you signed up for the lottery but weren’t able to register, your name has been added to the appropriate waitlist. Students who were able to register for their chosen class have also been added to the waitlist for the next class in sequence. Waitlist order was determined by the number assigned in the registration lottery and are now posted on the Sail Chicago Data Hub.
Crew Waitlist
First Mate Waitlist
Skipper Prep Class Waitlist
If you missed sign up for the lottery, add your name to a waitlist here.
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From the Safety Committee
After a long winter, the sailing season is finally here! Soon we'll all be heading to the harbor to board our boats. Skippers, as you gear up and get ready to set sail, here are a few important reminders:
Always Check your Boat's Status Before you head to the harbor, log on to my.sailchicago.org and review the status of your boat on the Fleet Status page. Are there any issues or warnings that you should be aware of? More importantly, has your boat been taken out of service? Remember, you are responsible for knowing the maintenance status of your boat. Sailing a boat that is out of service is the same as sailing a boat without a reservation. This is a serious rule infraction.
And while you're on my.sailchicago.org, take a moment to review the current wind/wave conditions and the weather forecast for your sail.
Carefully Complete the Pre- and Post-Sail Checklists The checklists are an essential and required part of every sail you do. They ensure that you have put eyes on and assessed your boat’s critical systems and safety equipment before setting sail, and that you consistently close up the boat after sailing completes. These checklists are also the primary way skippers communicate maintenance issues — even small ones — to our boat maintenance team. Remember, failing to complete the checklists is an infraction of Sail Chicago rules.
Proceed with Caution We're all eager to get out on the water, but for most of us, it's been at least six months since our last sail. Our skills are rusty! Keep that in mind as you head out on your first sails of the season. Bring along another skipper or experienced crew. Use careful judgement about the wind and wave forecast, and be conservative in estimating your own skills. Let's make sure our sailing this summer is safe and fun — see you out on the water!
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Race with Sail Chicago!
Racing officially starts on Wednesday June 11. Can't wait? You don't have to. Racing Tiller Times are back and will start Wednesday May 14. You need to register to race or do racing tiller times. Registration is $100 and covers all twelve races.
There's a "racing" Slack channel where more detailed updates will pop up from time to time. Or if you don't Slack, you can email us at race@sailchicago.org, although that email isn't checked as often as the slack channels are. We are also hosting a racing happy hour on June 12 for additional racing information or check out our racing page at Sail Chicago racing. You can also sign up on Sail Chicago > course availability.
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Reminder: Time Policies
Tiller Times are one of the most important ways that students can practice their skills, and all students are strongly encouraged to take advantage of them. Unfortunately, demand is high, and available Tiller Times are limited. Here's a reminder about our Tiller Time policy:
1. Every student is limited to four (4) Tiller Times per season. You will not be able to sign up in advance for more than four.
2. If you cancel your seat on a Tiller Time with less than 24 hours notice, it will count toward one of your four Tiller Times.
3. However, if you sign up for a Tiller Time less than 24 hours in advance, it will NOT count towards one of your four Tiller Times.
Students should practice as much as they can, and we want to make sure that everyone has a chance!
Remember to join the #tillertime channel on Slack. As Tiller Times become available for signup, notice will be posted there.
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 Social News
Season Kickoff, May 17, 3-6pm: Join us for 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. This is a complimentary event for Sail Chicago members and students and all may bring a guest. Snacks and drinks will be provided.
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Racing Happy Hour, June 12: Learn about Sail Chicago’s racing program and meet other racing members. This event is complimentary for Sail Chicago members and students and your first drink is included so signup below today!
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Mark your calendars for the following summer events!
Racing Happy Hour, June 12: Learn about Sail Chicago’s racing program and meet other racing members. This event is complimentary for Sail Chicago members and students and your first drink is included. Signup to come .
Friends & Family Picnic, July 26: Share in the joy of sailing! This will be a paid event for Sail Chicago members and students, with lunch included. Details to come!
End of Year Dinner, October 23rd: Come celebrate the end of the sailing season at Columbia Yacht Club! This event will directly follow the Annual Membership Meeting. Details and signup to come!
Keep up to date with additional social news on the Slack General channel. Our schedule is also available on the calendar located in your my.sailchicago portal.
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Cruising 2025!
Sail Chicago has big updates to its 2025 Cruising Program! Building on a strong cruising foundation, we’re bringing the Basic Keelboat program structure to our cruising program to make it easier to get started, easier to practice, and easier to grow. The previous six-session cruising class is being replaced with the following:
Cruising First Mate is an introduction for sailors new to cruising. You’ll get familiar with the boat and build confidence as part of a crew (4 sessions).
Cruising Skipper Prep is for those ready to be evaluated as a skipper. This class focuses on the full range of skills needed to safely take out a boat on your own. Confident students can then be checked-out as new cruising skippers (4 sessions).
Practice: One of the best ways to get time on the water is through Cruising Tiller Times. We also plan to designate a first mate for each cruising class and other program/private sails. This is great way to get time at the helm and learn what it takes to lead a class. If you’re thinking about teaching tiller times or becoming an instructor, this is a great place to start.
Greater Alignment with US Sailing: This year Sail Chicago will be taking steps to align its program with US Sailing’s Basic Cruising Curriculum. Our past cruising class has primarily focused on Sail Chicago boats, but in 2025 we are expanding to prepare skippers to command other cruising boats in various waters and conditions.
These changes mark an exciting moment in the evolution of Sail Chicago’s cruising program and will make cruising available to more of our members, expand practice, and create a rich pipeline of competent and confident cruising skippers. See you on the water!
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Annual Dues
It’s time 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.
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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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