Types of Sailing Adventures on Lake Michigan.  Never been sailing, and not sure what type of experience you would like? Let us share some of our most popular requests.



Whether you’re visiting Chicago for the weekend, or have been living in the area all your life, setting sail along Lake Michigan and soaking in the sites is timeless. We can take you along downtown to see Navy Pier, the water cribs, and so much more.



“I love the fact that there’s no motor. It’s quiet, peaceful and romantic.” “It’s nature pushing us not a motor — it’s very romantic.” — Captain Jeff

We love helping our passengers plan the perfect date. We have helped coordinate everything from engagement proposals to anniversaries, and every time it has proved to be something special. You tell us what you want, and we’ll take care of the rest, so you can enjoy a candlelight dinner for two on the dock.



If you’re looking for something a little more turned up, we’ve got you covered. So invite all your friends and step aboard any one of our sailboats for the ride of your life. Besides, who said speed boats get to have all the fun?

At the end of the day, we’re a people that loves the art of sailing, and we hope to share that passion with you. Give us a call today and book your next Chicago sailing adventure. We look forward to providing you with the exact luxury charter you desire.




Nothing beats the look of Chicago’s skyline at sunset. That’s why it’s one of our most requested times to rent a sailing charter. It’s the perfect setting for a romantic getaway, or spending time with loved ones.


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