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With Captain
There are very few Catamarans in Chicago and only one that is available for you to learn to sail. Our program is the only one in Chicago that offers Catamaran Certification that is accepted internationally. Rates: - 2 hours: $900 - 3 hour: $1200 - 4 hour: $1400 Your private lesson for up to 6 people will include: - Sailing out of Monroe Harbor on a 38' Luxury Sailing Catamaran (equivalent to a 70' monohull- more than enough room for your group) - Private instruction for up to 6 ppl. (4 is ideal for private lessons) - Captain & Instructor - Lesson Plan and Study Materials - Large Yeti Cooler and Refrigerator - Full Kitchen (Galley) with working stove/oven - Bluetooth Radio - Barbecue Grill - Floatie Toys for water fun - Lessons, Tour, Chill Out, Party Cruise/ BYOB or combo - It's all about customization.
Captain Jim
131 total bookings
Best of 2025
- Capacity
- 6 guests
- Tours, Lessons, and Diving
- Sailing Lessons
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
- Lagoon
- 380
- Capacity: 6 people max
Safety Equipment
Life Jackets (1)
Operating Equipment
GPS ChartPlotter
Guest Amenities
Oven
Sun Protection
Toilets (1)
Leisure & Entertainment Equipment
Bluetooth
Sound System
Departure Location
You’ll get helpful information for your departure after your booking is confirmed.
Street Address For Arrival
400 East Monroe Street
Chicago, Illinois, 60601
United States
Departure Location
41.881969034755,-87.615236439148
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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