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Frequently Asked Questions


How do I schedule my Sail?

If you want to schedule a private cruise or lesson, contact the office or go HERE




Can I Bring a Guest?

YES! For a limited time, we can offer your guest 70% off our Trial Weekend Membership. Normally $300, special- $90.

Study Guide for EVERYONE. 

Newbies: Beginners Study Guide, you will have much more fun on your sail if you know the basics! We also highly recommend reading SAILING FOR DUMMIES!



What should I wear?

NOTE: It may be up to 20 degrees colder on the lake, bring extra cloths especially in May and June, Sept. and Oct. (Knit hat and gloves all good!)

A waterproof jacket or windbreaker is a good idea in case the weather changes; try to avoid denim, cotton or leather, think cloths that dry quickly. If you booked a private cruise and plan on swimming, bring a suit and towel. Light-soled, closed-toed shoes are recommended. Sandals will also work but offer less protection. For your safety and comfort, no high heels please.


Do I need any previous sailing experience?

No. We welcome all experience levels and our sails. Interested in learning? We are structured so you can learn at your own pace.


Do I need to know how to swim?

No. Our boats are quite stable. As an added safety measure and in compliance with USCG standards, each boat is equipped with enough adult-sized life jackets for everyone aboard.


Is tipping appropriate?

For private cruises and catamaran cruises and Open Sails, it is customary to tip between 10%-15%. For other sails, please do not tip.


You may bring whatever you like, Captain's discretion on consumption during sail. (We do love to hang-out afterwards & enjoy a cold one!)

What is a typical class size?

Four to six students.


When are you open?

Our season runs mid-May through mid-October (Sometimes into Nov!)  We sail 7 days a week, weather permitting. SAILING SCHEDULE. Private cruise times can be customized to suit your schedule.


How do I find you?

Since the harbor has no real physical address, GPS and online directions are unreliable. We are located in Monroe Harbor, Cul-de-sac at Monroe and Lake Shore Drive in Chicago. Go here for Map & Directions


Where can I park?



What if I get sea sick?

If you are prone to motion sickness, any of the methods you may have tried before should do the trick (e.g., Dramamine, pressure point bracelets, or ginger candy). If it should happen anyway, let your Captain know immediately. We have additional ways of helping you get your sea legs under you!


What if the weather is bad?

Safety is our #1 priority. Cruising credits will be given for inclement weather, which will be determined by the Captain. Please refer to our Weather Cancellation Policy and Cancellation Policy for details. 


What if there is no wind? 

Unfortunately, we do not control the wind. However, we do have a motor and we will do everything we can to ensure you have fun. You can enjoy swimming, music, fabulous views, and good company.