About SailingChi

At SailingChi, we redefine what luxury sailing means on Lake Michigan. You’ll enjoy Chicago’s stunning skyline, dramatic sunsets, and the vast open water from the comfort of an elegant sailboat — all curated with meticulous attention to detail and a bespoke service ethos. Guests consistently praise our ability to tailor every voyage to the moment, whether for an intimate anniversary, exciting group celebration, or a truly unforgettable private charter experience.

Our Founder — Captain Charles

Captain Charles brings both passion and precision to every journey. With deep experience on the water and a love for showing Chicago from its most breathtaking vantage point, he has built SailingChi around personal connection and high-touch service. Under his leadership, every charter is more than a trip — it’s a crafted experience designed around your desires.

Whether you seek a romantic sunset sail, a lively celebration with close friends, or a signature corporate experience, Captain Charles ensures your time aboard is seamless, comfortable, and thoroughly memorable. Client reviews highlight the warmth, professionalism, and personalization that define every SailingChi adventure.

What We Offer

• Private Luxury Sailing Charters — Tailored experiences on our premium yacht Guppy, complete with elegant interiors, spacious comfort, and high-end amenities.
  
  

• Custom Celebrations & Events — From proposals and anniversaries to sunset soirées and milestone gatherings, each sailing is crafted to reflect your vision.
  
  

• Personalized Service — Guests consistently highlight attentive communication, flexibility, and outstanding hospitality from start to finish.
  
  

We believe the best experiences are shaped by the people who share them — and nothing rivals the magic of Chicago’s skyline seen from the water.

Come aboard—let’s set sail.