Navigating Chicago Off-Season: Urban Skills for Better Sailors

Every winter in Chicago, there’s a moment, usually when the lake freezes over and the wind cuts a little too hard, where I start to miss sailing in a way that feels almost physical. The lines, the rhythm, the feeling of reading the wind… it all just disappears for a few months. And if you’re anything like me, you start to wonder: am I going to be rusty when the season comes back?

The good news is, you don’t have to be. Even in the middle of a Chicago winter, there are small, everyday ways to keep your sailing brain switched on, yes, even during something as routine as your commute. Here are a few ways to keep your skills as sharp as your sails while we wait for the water to thaw.

1. Knot-Tying Practice

   Knowing how to tie knots is one of the most critical skills in sailing. Having the muscle memory to do so is even better. Keep a 2-3 foot length of line in your bag. Practice essential knots like the bowline, clove hitch, and figure-eight while on the L or the bus to build muscle memory. It will be much easier when you’re on the water to have already practiced those skills off-season! 

   

2. Use the Wind Between Buildings to Imagine Sailing Conditions

   Did you know that Chicago’s architecture creates unique wind patterns that mimic complex sailing conditions? Skyscrapers create "wind tunnels" where air is compressed and accelerated. Observe flags on different buildings; they often point in different directions due to these eddies. This mimics the "dirty air" or "wind shadows" you encounter when racing near other boats or large shorelines. 

   
   

   During your afternoon commute, observe if the wind is shifting. In Chicago, thermal breezes often pull cooler air from the lake toward the warmer land in the afternoon, significantly impacting the gradient wind. How would this affect your boat? 

   
   

   

3. Read the Clouds Over Lake Michigan!

   There are three big cloud types; cumulus, cirrus, and stratus. Cumulus clouds are fluffy, white cotton balls that indicate fair weather, but if they grow vertically into "anvil" shapes, they can signal brewing thunderstorms. Cirrus clouds are thin, wispy, high-altitude clouds. A few mean fair weather, but an increase in coverage suggests a change in weather, often a warm front within 24 hours. Stratus clouds are low, gray, featureless clouds that cover the sky like a blanket, often bringing drizzle or light rain. Watching the sky for these clouds can help you predict the weather–and your commute as well. When it’s time to set sail, you’ll already be a master at predicting weather changes. 

   

   
   

4. Read and Listen During Your Commute

   Listening to a podcast or reading a book is a much better term to use than “studying.” While on your commute, it’s important to keep up-to-date on all the sailing terminology so that you don’t forget it. Listening to sailing podcasts can help you keep up with terminology, racing tactics, and cruising stories. Reading books on sailing can do the same–and give you visuals to help reinforce fundamentals. One of the best podcasts to help refresh your memory is Bar Karate Sailing Podcast.

   

5. Watch YouTube on Your Phone!

   Most teachers would tell you to put your phone away, but if you’re on the bus or on the L, your phone can serve as an essential tool to help keep skills sharp. While you’re waiting to get to your stop, watch YouTube videos! The School of Sailing is a YouTube channel "packed with lessons from beginner basics to next-level mastery." From aesthetic videos to short lessons on common vocabulary--their videos will have all of us ready to get back on the water!

Off season can be a slow time for us all. Shorter, colder days have us aching to get back onto the waters of Lake Michigan to set sail yet again. Though we can’t control the weather, we can control what we decide to do during the off-season. Our commute may seem like a boring, everyday necessity, but we can turn it into a valuable time to practice our sailing skills so that we are fully equipped and ready to get back in the water to practice the real deal.

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Have a question? Email us at info@greatlakessailing.us