Why We Love Sailing in Chicago – A Personal Note from the Captains

There’s something special about sailing in Chicago. It’s not just the skyline, or the breeze off the lake, or even the way the sun sets over the water; it’s all of that, and more.

As captains who have spent countless hours on Lake Michigan, we’ve come to understand what makes this place so unique. Whether you're a lifelong Chicagoan or visiting for the first time, there's something deeply moving about seeing the city from the deck of a sailboat.

Here’s what sailing in Chicago means to us, and why we’re proud to call it home.

The iconic waterfront provides a stunning contrast to the dense urban environment, with a prominent pier jutting out into the shimmering water.

🧭 From Different Paths, One Passion

We may have arrived at Windy City Sailing through different journeys, but we share the same love: the magic of sailing on Lake Michigan.

Captain Josef:

I grew up on the North Side of Chicago, Roscoe Village was my backyard, and Wrigley Field was just down the street. But I didn’t truly fall in love with the water until I moved to San Francisco in the late 90s.

That first time I stepped onto a sailboat on the Bay, I felt something shift inside me. The wind, the waves, the silence broken only by the creak of the rigging — it gave me peace, clarity, and a sense of freedom I’d never known.

When I came back to Chicago, I wanted to bring that feeling home. And that’s how Windy City Sailing began, with a dream to help others experience the beauty of sailing, right here in our own city.

Captain Mike:

For me, sailing has always been part of life. Growing up near the lake, I had the privilege of learning early on how to read the wind and feel the rhythm of the water. Even during my years as a firefighter, the lake remained my escape, my sanctuary.

Sailing isn’t just a hobby for me. It’s a way to slow down, breathe deep, and appreciate the moment. That’s what we try to give every guest aboard the Nebula — a chance to unplug, unwind, and connect with the lake in a meaningful way.

🏙️ What Makes Chicago Sailing Unique

There are plenty of places to go sailing around the world, but nothing compares to gliding past the iconic Chicago skyline on a summer afternoon.

Here’s why we love sailing in Chicago:

🌆 The Skyline

Chicago is one of the most architecturally rich cities in the world. Seeing those towering buildings from the water, especially at sunset, is unforgettable. The lights reflecting off the lake, the contrast between the urban landscape and the open water… It’s breathtaking.

🌬️ The Wind

Let’s be honest, we earned our nickname for a reason. There’s a certain thrill that comes with harnessing the wind on Lake Michigan. On a breezy day, when the sails catch the gust and the boat leans into the current, it feels like flying.

It keeps things exciting, and it reminds us why we fell in love with sailing in the first place.

🐿️ The Nature

You might not expect it in a major city, but Lake Michigan is full of life. You’ll see gulls riding the thermals, dolphins (yes, really!), and on quiet mornings, even a curious seal or two. The lake is alive, and every charter offers a new opportunity to witness its natural beauty.

📅 The Seasons

One of the best parts of sailing in Chicago is experiencing it in every season. Spring brings fresh air and the promise of adventure. Summer is full of laughter, long days, and golden-hour sails. Fall paints the sky in warm hues and crisp winds. And winter? Winter gives us stillness, moments of quiet reflection as the boat cuts through calm waters under gray skies.

Each season tells its own story, and we’re lucky to live them all.

💡 Our Favorite Part? Sharing It With You

At the end of the day, sailing isn’t just about the boat, the route, or the weather; it’s about the people.

Whether it’s a couple celebrating an anniversary, friends raising a glass to friendship, or a family reconnecting on the water, we love being part of your story.

There’s nothing quite like watching someone step onboard the Nebula for the first time — a little unsure, maybe a little nervous — and then, by the end of the trip, seeing them relaxed, smiling, and already asking when they can come back.

Those are the moments that remind us why we do what we do.

🛥️ A Message from Us to You

If you've never experienced Chicago from the water, we hope you’ll give it a try. You don’t need to be an expert to enjoy sailing, just a heart open to discovery.

From the moment you step aboard the Nebula, our goal is simple: to make you feel welcome, inspired, and connected to the lake, to each other, and to the joy of being out on the water.

Thank you for letting us share our passion with you.

We look forward to welcoming you aboard soon.

Warmly,

Captain Josef Erlemann & Captain Mike

Founders, Windy City Sailing

📸 Ready to See Chicago from the Water?

Book your private charter aboard the Nebula today and experience the beauty of Lake Michigan for yourself.

📍 Location: Chicago Lakefront

⛵ Vessel: Nebula – A beautiful 42-foot Beneteau Oceanis

📅 Season: May through October

👥 Perfect For: Weddings, anniversaries, corporate events, bachelor's/bachelorette parties, or simply enjoying the ride.

👉 Book Your Charter Today!