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Frequently Asked Questions

⛵ Scheduling a Sail

How do I schedule my sail?

📱 Students: Try our Scheduling App for the easiest booking experience!

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📍 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.

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👥 Bringing Guests

Can existing students bring a guest?

 

📆 Cancellations, Rescheduling & Weather

What’s your cancellation policy?

  • We require at least 48 hours notice for cancellations or rescheduling. Please refer to our Cancellation Policy and Weather Policy for full details.

  • Safety is our #1 priority. We make weather calls 2 hours before your sail.

  • If weather prevents sailing, Cruising Credits will be issued that may be used for any service we offer and they never expire.

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🍹 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!)

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💵 Tipping Etiquette

  • For Private Charters, Catamaran Cruises, or Open Sails, a tip of 10%–15% is customary.

  • Students & Club Members: You may tip a USCG Licensed Captain ONLY, Coast Guard regulations.

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🎁 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.

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⛵ Learn to Sail Program

Tell me more about your sailing lessons.

  • 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. 

  • 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.

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👚 What Should I Wear?

What’s the dress code for sailing?

  • 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.

  • A waterproof or windproof jacket is a good idea. Avoid cotton, denim, or leather—opt for quick-drying fabrics.

  • If you’re planning to swim, bring a swimsuit and towel.

  • Light-soled, closed-toed shoes are ideal. Sandals work too, but no high heels, please!

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📅 When Are You Open?

  • We sail 7 days a week, mid-May through mid-October (sometimes into November).

  • Private cruises are flexible—pick your time!

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🌬️ 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.

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