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Sailing Lessons with Chicago's #1 Rated Sailing SchoolSailing Lessons with Chicago's #1 Rated Sailing SchoolSailing Lessons with Chicago's #1 Rated Sailing SchoolSailing Lessons with Chicago's #1 Rated Sailing School

Chicago Sailing Lessons: Master Sailing on a 33ft Hunter Yacht with Expert Instructors

With Captain

4 bookings
·
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    This date is available.

With over 20 years in the business, we have successfully trained 1000's of sailors and skippers. Join our Learn to Sail Chicago program and master the art of sailing aboard the Marlow-Hunter 33 Sailing Yacht. This comprehensive course is designed to provide you with the skills and confidence needed to navigate the waters of Lake Michigan. Rates: • 2 hours: $500 • 3 hour: $600 • 4 hour: $700 You and your guests will sail out of Monroe Harbor, located in downtown Chicago, and experience the "Sailing Lifestyle" while also learning the basics of sailing. Our experienced team has trained many sailor and skippers over the years and we can tailor your private lesson to include swimming, cooking out, or enjoying the beautiful skyline of Chicago with your favorite drink in hand. Whether you want a challenging or more relaxed experience, simply communicate your expectations to the Captain and we will make sure to meet your needs.

Captain Jim

Captain Jim

131 total bookings
Best of 2025
Capacity
6 guests
Tours, Lessons, and Diving
Lessons
Captain Jim

Captain Jim

131 total bookings
Best of 2025

We've had so much fun on our annual Bluewater Magellan trips over the years that we decided to invest in our own catamaran. We offer private sailing charters on Lake Michigan in the summer and in the winter we take the boat somewhere warm to offer multi-day cruises. Throughout all the growth and change, one thing will always remain the same: our commitment to providing the best sailing experience possible. Whether it's local or tropical—we want you to love sailing as much as we do and will do our best to make sure you have a great time!

Features & Details

  • Marlow-Hunter
  • Marlow-Hunter 33
  • Capacity: 6 people max

Safety Equipment

Life Jackets (1)

Guest Amenities

Cabins (1)
Toilets (1)

Leisure & Entertainment Equipment

Bluetooth
Sound System

Departure Location

The boat's approximate location on a map

You’ll get helpful information for your departure after your booking is confirmed.

Street Address For Arrival

Street Address For Arrival

400 East Monroe Street
Chicago, Illinois, 60601
United States
Departure Location

Departure Location

41.881920397112,-87.615097812891
Chicago, Illinois, 60601
United States

Cancellation Policy

50% refund of offer amount up to 14 days prior.

Additional Terms & Information

- Cruising Credits will be issued if there is inclement weather and you can reschedule with us anytime. - Weather- We will make the call on weather 2-hrs before your sail, if you don't hear from us, your sail is a go!

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With Captain
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  • With Captain Only