The TellTale July 2026

Sail Chicago Tell Tale
Issue 7: July 2026

New Skipper Journey 

Two years ago, 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 year 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

Social News

Friends and Family Picnic
Join us for Sail Chicago's annual Friends & Family Picnic at Belmont Yacht Club! This is one of our favorite events of the season and a great opportunity to introduce your family and friends to the Sail Chicago community.

This year's picnic will once again be hosted at Belmont Yacht Club, where we'll have access to the indoor clubhouse, rooftop deck, and outdoor picnic area. Spend the afternoon enjoying delicious catered tacos from Happy Taco Chicago (including vegetarian options), beverages, beautiful harbor views, and great company.

Whether you're a longtime member, a current student, or new to Sail Chicago, everyone is encouraged to attend! Guests will have the opportunity to meet members, learn more about Sail Chicago's programs, and tour Priorities, Sail Chicago's 34-foot cruising sailboat.

We hope you'll join us for one of our favorite events of the season! This event will be held rain or shine.

When: Saturday, July 25th, 11 AM - 2 PM
Where: Belmont Yacht Club, 3600 N Recreation Dr.
Cost: $15 per ticket

Register here

July Photo Contest!

Got Great Photos? Share 'Em! Send your favorite pictures for a chance to win the July Best Photo award! Great photos will also be featured on Instagram, in The Telltale, and at the End of Season Dinner!

Upload photos
Thanks to everyone who came to our June Happy Hour. It was a very hot day in Chicago but the showing was great.

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 all our members to chip in and help us succeed, and skippering MCO's or Tiller Times is a great way to contribute. 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.

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.

Racing News

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.) 

The Rainbow Regatta is July 26 at Monroe Harbor. Although this event is designed to accommodate new racers, lots of experienced sailors also participate. Stay tuned the the racing slack channel for more information.

The Verve inshore is set for August 21-23, 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.

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.

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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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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The TellTale June 2026