3rd Coast Cruising – Legend 31
Sail Chicago with one of the city’s most established sailing schools.
3rd Coast Cruising has been introducing people to sailing on Lake Michigan for more than 25 years. Whether you want a relaxing private cruise, a hands-on sailing lesson, or a little of both, our experienced team will customize the experience around your group.
You’ll sail aboard a Hunter Legend 31, a comfortable and responsive sailboat that accommodates up to six guests. Enjoy Chicago skyline views, learn the basics of sailing, take the helm, or simply relax with friends and family.
Guests are welcome to bring food and drinks. Swimming may be available when conditions allow, and all required safety equipment is provided onboard.
From first-time sailors to experienced guests looking to sharpen their skills, 3rd Coast offers much more than a typical boat ride; it’s a genuine Chicago sailing experience.
Sail Chicago with one of the city’s most established sailing schools.
3rd Coast Cruising has been introducing people to sailing on Lake Michigan for more than 25 years. Whether you want a relaxing private cruise, a hands-on sailing lesson, or a little of both, our experienced team will customize the experience around your group.
You’ll sail aboard a Hunter Legend 31, a comfortable and responsive sailboat that accommodates up to six guests. Enjoy Chicago skyline views, learn the basics of sailing, take the helm, or simply relax with friends and family.
Guests are welcome to bring food and drinks. Swimming may be available when conditions allow, and all required safety equipment is provided onboard.
From first-time sailors to experienced guests looking to sharpen their skills, 3rd Coast offers much more than a typical boat ride; it’s a genuine Chicago sailing experience.

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Chicago, Illinois, United States
Captain Jim has more than 30 years of sailing experience and has taught thousands of students on Lake Michigan. As the founder of 3rd Coast Cruising, he's helped complete beginners become confident sailors, boat owners sharpen their skills, and experienced crews prepare for bigger adventures. His style is hands-on, relaxed, and tailored to each group, whether you want to learn, take the helm, or simply enjoy an unforgettable sail.
Captain Jim has more than 30 years of sailing experience and has taught thousands of students on Lake Michigan. As the founder of 3rd Coast Cruising, he's helped complete beginners become confident sailors, boat owners sharpen their skills, and experienced crews prepare for bigger adventures. His style is hands-on, relaxed, and tailored to each group, whether you want to learn, take the helm, or simply enjoy an unforgettable sail.
Security deposit is not required
A refundable deposit is not required by the charter operator.
Free cancellation up to 14 days prior to trip
You can cancel or modify your booking up to 14 days before the trip date, free of charge. If you cancel or modify your booking later, or fail to show up, you'll forfeit 100% of what you've paid.
Reserve with a 10% booking deposit, pay the captain the rest
When the captain confirms your trip, BoatBooker charges your credit card a 10% booking deposit to guarantee your reservation.
The remaining balance is to be paid directly to the charter operator on or prior to your trip date in one of the following payment methods:
Visa
Mastercard
American Express
PayPal
When paying the remaining balance with a credit card, an additional 4% charge will apply.