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Summer is in full swing, and this Telltale shows it! Valuable tips are below, along with social events open for registration. We hope to see everyone at Belmont Yacht Club for the Friends and Family picnic. If you haven't been inside, it's a fun place to hang out in a fantastic setting. If you aren't sailing enough, get on the "share-a-sail" slack channel and don't be shy! Create a post and head out on the water! — Meighan Depke, Editor
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The New Skipper Journey
Last year, I attended our Skipper-to-Skipper happy hour and was asked to say a few words. I gave three bits of advice for our new skippers and I hope they are worth repeating this year.
First, make friends and go sailing! My first year as a skipper, I was fortunate to hit it off with another board member, Daniel Hazlett. We sailed together a dozen times that summer, and I learned so much from him. It helped that Daniel is one of our instructors and a great sailor, but most of what I learned was to trust my instincts, to continue to practice, to be prudent, to try things out and observe what happens, and to keep learning.
My second piece of advice is to not just sail, but to reserve boats as the skipper. I've talked with many new skippers on MCO's, and every one of them says the same thing—it feels very different to be the person in charge of a boat and its crew. You feel the weight of that responsibility, and that shapes your judgment. And careful judgment is what makes you a better sailor.
Which brings me to my third piece of advice: own your mistakes. Even the most experienced sailor can be humbled by wind and waves. This happened to me last week on an MCO I was hosting. The winds suddenly jumped from about 6 knots to 18 knots, and before we had a chance to heave-to and reef, I executed a series of tacks that nobody in my boat, including me, was comfortable with. So own your mistakes. Ask your fellow sailors and crew what they would have done differently. Report incidents when they happen. These are the best ways to learn. Sail Chicago is a learning community and as sailors, we're committed to spending our lives learning how to do this amazing thing even better.
— Gerry Stacy, Board Chair
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Single-Handed Sailing Pause
Upon recommendation of the Safety Standing Committee, the board of directors is pausing all single-handed sailing activities, effective immediately, to allow for the development of rules, better tracking, and formal skill/safety standards associated with this particularly risky sailing activity. We anticipate resuming single-handing classes and allowing single-handed sailing in 2026. If you have questions about this pause, please contact the On-the-Water Standing Committee leaders, Manny Conde (manoelconde@yahoo.com) or Matt Smith (matthew.reese.smith@gmail.com).
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New! Highly Experienced Sailors Accelerated Process
Sail Chicago welcomes everyone to our membership and a large part of our organizational focus is to introduce people to sailing and teach them how to be outstanding sailors. But Sail Chicago also welcomes experienced sailors! We insist that each new member go through our Skipper qualification process by taking our Skipper Prep class. This ensures that all members are well-acquainted with our boats, our procedures, and become properly oriented to Monroe Harbor.
However in rare cases, this requirement may be abbreviated for an individual upon the recommendation of the Instruction Team. You can review our Skippering Exception Process to learn more.
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Becoming a Skipper at Sail Chicago
At Sail Chicago, becoming a Skipper isn’t taken lightly—and for good reason. As a volunteer-run organization, safety and leadership are top priorities. To earn your Skipper status, you must complete the course sequence: Crew, First Mate, Skipper Prep and then pass the On-the-Water (OTW) Skill Standards Assessment (during your last Skipper Prep course or during a mid-season make-up skipper check out). After your OTW assessment, you’ll get an automated email with next steps.
You’ll need to complete the following items:
— Pass the US Sailing Basic Keelboat Exam (80 questions/80% correct to pass)
— Pass the Sail Chicago Rules & Policies Exam (33 questions)
— Sign the New Skipper Attestation
— Book 3 Private Sails as the skipper of record with at least one other Sail Chicago Skipper aboard as crew.
That’s it! Once these steps are complete, you can rent any of the Colgate 26 boats on your own. Also, if you are curious about other boats in our fleet, contact the boat managers for the Ideal 18s or the Rhodes 19s. These are smaller and more agile boats that are fast and a lot of fun to sail! Or, sign up for the First-mate Cruising class to learn more about our larger 34’ Cruisers!
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What a great day on the water!
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Julie Nguyen, Yi Du, Carlos Litovich, Dana McGarr
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I'm a New Skipper...Now What?
For new skippers/soon to be new skippers, congratulations! You've reached the end of our learn-to-sail classes and passed all your exams. Now what?
First, complete your three sails as “skipper of record”! All new skippers must complete three private sails as the “skipper of record” with another Sail Chicago skipper in attendance. Reach out to your fellow new skippers or other skippers you've met at events and ask them to join you. When your fellow new skippers ask for a skipper to be their first mate, volunteer to go along. Slack is also a great place to find skippers happy to share a sail. Meet people, continue to practice, and get out on the water.
Next, think about becoming a program skipper. Remember when you were new to Sail Chicago, waiting for your first class, and you were able to get out on the water for a sail by signing up for a Member Cruise Outing? Or when you were a student looking to practice, and you signed up for Tiller Times? Pay it forward! We rely on volunteers. Plus, there's no charge for you to reserve a boat for an MCO or Tiller Time—you sail for free. Look over the requirements for MCO and Tiller Time Skippers, and get in touch with our coordinators.
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Racing News
Racers, the Rainbow Regatta is July 12 at Monroe Harbor, 1pm start. Although this event is designed to accommodate new racers, lots of experienced sailors also participate. We have three or four Colgates set to race. If we get five they will have a dedicated start for our class. Anyone wanting to race may reserve a Colgate and register at rainbowraces.org. Or, contact tom.hafner@sailchicago.org. I will attempt to link up crew with skippers.
The Verve inshore is set for August 23 and 24, at Belmont Harbor. It's two days of racing, and a big party Saturday night at CYC Belmont. All boats should have experienced racing skippers. Feel free to register at vervecup.com/inshore or email tom.hafner@sailchicago.org to be added to my list of people looking for boats and boats looking for people.
Finally, join Wednesday night racing. The best value on the lake gets you unlimited Wednesday night races, unlimited Racing Tiller Times, and access to special events for $100. Ever wonder what it's like to be at the helm, run the foredeck, or set strategy for the starting line? You get to try out every position while expanding your skill set. Newbies welcome so come out and have fun with us. (You must have completed an SC crew class.)
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Become a Tiller Time Skipper!
We’re seeking skippers for Sail Chicago’s 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 and advance to skipper status. As a Tiller Time skipper, you become a vital link in this process. There are several advantages to being a Tiller Time skipper. They include:
— Sharing your love of sailing with committed and enthusiastic students
— Spending more time on the water without having to schedule a private sail
— Making new friends and sailing buddies
— Helping you decide if you’d like to become an instructor
— Completing five Tiller Times as a skipper fulfills your annual service requirement
To learn more and to find out if you’re eligible to become a Tiller Time skipper, contact Steve VanderVoort at tillertime@sailchicago.org.
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 Social News
Racing Happy Hour Recap: Thanks to everyone who came to Jackson Park Yacht Club for our June happy hour! It was a treat to hear from George Chlipala, longtime JPYC member. His insight into the rules and the thrill of racing gave us all a deeper appreciation for the sport. The gorgeous views from the venue made the evening even more memorable.
Lighted Boat Parade,
Saturday, July 12th, 9pm
Monroe Harbor
Sail Chicago will be decorating and entering Priorities in the parade at Monroe Harbor so come show your support! If you’re interested in joining the viewing party, want to help decorate, or hang out before the parade, please RSVP at: Lighted Boat Parade.
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Sail Chicago Annual Picnic + Short Sails
Saturday, July 26th, 11am-2pm
Belmont Yacht Club
For this year's annual picnic we'll have use of BYC's indoor space, roof deck, and outdoor picnic tables. Enjoy a fresh taco dinner prepared on-site by a live chef (vegetarian options available), drinks, and great company—all with stunning lake views. This event will be hosted rain or shine! Tickets are $20 plus fees.
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Short Sails: Signup for a short sail before or after the picnic to show your friends and family what sailing is all about. We'll have 3 Colgates and 2 cruisers taking passengers out for a quick Lake Michigan trip. This free event is weather dependent. All guests must be associated with a current Sail Chicago member. Signups are limited to one time slot on one boat per member.
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End of Year Dinner, October 23rd
Celebrate the end of sailing season at Columbia Yacht Club! This event will directly follow the Annual Membership Meeting. Details and signup to come.
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Interested in Instruction?
The Instructor Prep class gets you ready to teach at Sail Chicago! Candidates should have a minimum of two years skipper experience with Sail Chicago, and be confident and competent sailors. Prep begins with the Sail Chicago Skills and Standards for the Colgate 26 Instructor Exam. Candidates will then shadow a minimum of one Sail Chicago instructor and complete a shadow form. This is followed by two OTW classes with a Sail Chicago Instructor Trainer (certified Basic Keelboat Instructor). Instructor trainers will share learning practices that make Sail Chicago's classes safe and fun. Candidates will then demonstrate those practices. Finally, candidates will conduct a Tiller Time sail while being observed by Instructor Mentors. The Mentor then completes an observation form, gives solid feedback, and makes recommendations on improving teaching style.
Classes open soon, and beginning this year, we're offering this class free of charge! There is limited space, so start planning now! Contact leadinstructor@sailchicago.org.
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Need to Cancel a Reservation?
Plans change—we get it! If you've booked a Private Sail, Tiller Time, or Cruise, you can easily cancel your reservation through your my.sailchicago.org dashboard:
Go to the My Upcoming Reservations section. Find the reservation you'd like to cancel. Click Change in the top right corner. Select Cancel from the menu.
Note: Tiller Time reservations must be canceled at least 24 hours before the start time to receive a credit refund.
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Mid-season Skipper Check-outs
Have you completed your Skipper Prep course and received a Plan of Improvement (POI) instead of passing? Don’t worry—it's simply part of the learning process. Sail Chicago’s goal is to help you build the skills and confidence needed to skipper safely and successfully. So what’s next?
Practice with purpose: Sign up for Tiller Times and let your instructor know exactly what you want to work on—refine your approach, read the wind, or sharpen your boat handling skills. If your Tiller Time credits are all used, you can still join sessions with space available within 48 hours of the sail date. Or, join others on cruise outings or maintenance sails: Jump on a private sail with others to get more practice.
Ready for another try? Once you’ve had time to practice and feel confident, sign up for a Mid-Season Make-Up Skipper Check-out. We’ve scheduled these for July 10, July 19 and October 1 with more dates to follow. You'll enroll through your mysailchicago.org portal with a special passcode. Contact your instructor for the code to register.
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Leaving the Can Tip!
While skippering a recent Tiller Time, Max Maizels noticed this common mistake. The photo shows the foredeck person has placed the eye of the la zy line over the port bow cleat, and the eye of the active line in the water. Since there is no mooring line eye over the boat's wand, this setup will make return to can difficult. Rather than simply lifting the wand to retrieve the mooring line, the foredeck person will need to raise the wand and then struggle to grasp the line.
For more information, a companion video is posted on in slack channel #video.
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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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the
sailing is almost here, and it begins with the rollout of our schedule of classes! New and returning students can find information about the 
the 
Guy Whitney, a Sail Chicago member from the early days of the organization’s formation, passed away peacefully on January 23. Sail Chicago old-timers will remember him as a tough old salt who wouldn’t tolerate any nonsense. He was on the Sail Chicago Board for several years, and was in charge of maintenance when we had only Rhodes 19s and a couple of cruising boats in our fleet. Younger members might remember him as one of the tender drivers who helped us get to our boats in Monroe Harbor throughout the summer months.
Season 2025 will have new instruction team leaders: Tom Hertel, Lead Instructor, and Brian Huang, Deputy Lead Instructor. Much thanks to the outgoing lead instructor, Monte Lewis who received an award recognizing his contribution at the annual dinner meeting on October. Season 2024 closed with 10% more learn to sail classes than 2023 and the student surveys show the sailing instruction program overall receives high scores.
Sail Chicago’s new boat is a 15.5-foot used Novurania Fiberglass with Hypalon inflatable pontoons and a 90hp Yamaha outboard motor. This boat is to be used primarily as a Maintenance Utility Rigid Inflatable Boat (RIB). It will be docked in a 30’ slip at Belmont Harbor during the summer, close to a hydraulic lift (for stepping and un-stepping masts) and a marine-grade fuel pump for re-fueling our fleet of Colgate and Rhodes.
