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Chicago's #1 Learn to Sail Program

Discover the thrill of sailing with 3rd Coast Cruising - the premier Learn to Sail Program in Chicago! With almost two decades of experience and training thousands of Sailors & Skippers, we have completely transformed the way sailing is taught in the city.


Our program is unique compared to other sailing schools as we cater to sailors of all levels and backgrounds, offering flexible online scheduling that allows you to learn at your own pace, even with the busiest of schedules. Our program offers:

  • A wide variety of certifications including the highly sought-after International Cert. (SLC)

  • Unlimited seatime and hands-on practical experience with Memberships, giving you access to a diverse range of boats, including our impressive 380 Lagoon Catamaran

  • An emphasis on "Skipper Training" for those interested in bareboating or boat ownership.

  • Private and group lessons are offered out of Monroe Harbor, Chicago.

  • An unparalleled, fun learning experience that you'll never forget!

Our Trial Membership is the perfect way to sample what our program has to offer and is recommended for all new sailors.

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Trial Membership

Trial Membership 

Buy One 3-hr. Sail, $300, get up to 3 Free

In the current age of digital technology, sailing is a skill that is becoming more and more uncommon, and mastering it is even rarer. Whether you are passionate about water sports or committed to mastering this skill, our Trial Membership offers an ideal starting point. It enables you to experience our teaching methods first and and "test the waters" to determine whether our program is right for you before committing to one of our Memberships.

Our Trial Membership offers the following:

  • Flexible online scheduling from May to October, 7 days a week

  • 3-hour sails available at 6:30 pm M-F and 10 am, 1:30 pm, and 5 pm Sat & Sun

  • Lessons tailored to the experience level of both novice and experienced sailors

  • All Seatime will count towards your Certification

  • Options for singles or couples.

Get Started, Trial Membership Discount

By completing the following steps, you can qualify for a special discount on our membership:

  1. Complete Trial Membership Survey (2 mins)

  2. Take our Beginner Test 

Once you complete these steps, we will send you your offer!

Alternatively, you can purchase our New Sailor Package, which includes one 3-hour sail for $300 and two additional sails for free.

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