
Frequently Asked Questions

⛵ Scheduling a Sail
How do I schedule my sail?
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Club Members: Club Members Scheduling
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Non-Members: Non-Club Member Scheduling
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Private Cruises or Lessons: Schedule a Private Experience
📱 Students: Try our Scheduling App for the easiest booking experience!
📍 Location & Parking
We're located in Monroe Harbor, at the cul-de-sac where Monroe meets Lake Shore Drive in Chicago.
Since GPS is unreliable, please use our Map & Directions to find us easily.
👥 Bringing Guests
Can existing students bring a guest?
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Non-Members: Non-Member & Guest Instructions
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Club Members: Scheduling Instructions
📆 Cancellations, Rescheduling & Weather
What’s your cancellation policy?
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We require at least 48 hours notice for cancellations or rescheduling. Please refer to our Cancellation Policy and Weather Policy for full details.
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Safety is our #1 priority. We make weather calls 2 hours before your sail.
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If weather prevents sailing, Cruising Credits will be issued that may be used for any service we offer and they never expire.
🍹 BYOB Policy
Yes, we’re BYOB-friendly!
You may bring your own food and drinks, subject to the Captain’s discretion during sails. (For lessons, we love hanging out after for a celebratory drink!)
💵 Tipping Etiquette
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For Private Charters, Catamaran Cruises, or Open Sails, a tip of 10%–15% is customary.
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Students & Club Members: You may tip a USCG Licensed Captain ONLY, Coast Guard regulations.
🎁 Deals for New Sailors
Any special offers?
Dip your toes in with our Trial Membership Package. Buy 1, get 3 free. It’s the perfect way to see if we’re the right fit for your summer on the water.
⛵ Learn to Sail Program
Tell me more about your sailing lessons.
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Our program allows new sailors to start at any time, with flexible progression. You’ll gain hands-on seatime, take on leadership roles, and work toward certifications like Mate or Master of Vessel.
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Check out our Trial Memberships to find the right path for you.
📘 Students, Before Your First Sail
Is there anything I need to do?
Yes—whether you’re a student, club member, or guest, please review the Beginner Study Guide and take the quiz before your 1st sail. Please review the New Sailor material and take the test.
👚 What Should I Wear?
What’s the dress code for sailing?
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Expect it to be up to 20° colder on the lake, especially in May, June, Sept, or Oct. Bring layers, including a knit hat and gloves if needed.
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A waterproof or windproof jacket is a good idea. Avoid cotton, denim, or leather—opt for quick-drying fabrics.
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If you’re planning to swim, bring a swimsuit and towel.
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Light-soled, closed-toed shoes are ideal. Sandals work too, but no high heels, please!
📅 When Are You Open?
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We sail 7 days a week, mid-May through mid-October (sometimes into November).
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Private cruises are flexible—pick your time!
🌬️ What if there is no wind?
No problem! We’ve got a motor—and we’ll make it fun regardless. Enjoy swimming, music, beautiful views, and great company.