Registration · Scheduling · Directions
Everything for your first sail.
Register once, request your sails, and watch your inbox. Most sails leave from Monroe Harbor. Your confirmation email always has the exact boat and gate.
Scheduling
Three steps to a spot on a boat.
The club uses a short registration and waitlist process so boats go out full and everyone gets a fair shot at the popular dates.
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Register with the school
Everyone sails with their own account and unique email. Create or manage your account.
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Request to Sail (RTS)
RTS is a waitlist, not a guaranteed spot. If space opens, you are notified — typically within about five days. You can also book any open sail directly.
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Watch your inbox
You get a confirmation when assigned to a boat and a reminder the day before with final details. No email? Check your Mindbody profile and make sure you are opted in.
Important: when you register, check “Get a heads-up before bookings.” If it is unchecked, you will not receive confirmation emails with directions.
Bringing a guest
Two sailors, two accounts.
If your package is shareable, scheduling for two is simple: book yourself, log out, then book your guest using their own email as the username.
- Unique email per sailor
Each person registers separately. Have your guest mention your name on their registration.
- Guest option
A 3‑hour single sail is $75 with promo code SingleTrial. The Trial Membership gives a guest three free sails.
- Groupon sailors
Register on the non-member path, enter your redemption code, and put “NA” if you are not using Groupon.
Directions
Meet at Monroe Harbor.
Chicago's harbors do not have traditional street addresses, and GPS can be misleading. Use the address below for rideshare drop-off, then follow the harbor path — not your map pin.
- Approximate address
400 E Monroe St, Chicago, IL. We are not inside the Chicago Yacht Club.
- The gate is locked
Wait outside the Monroe Dock entrance and a crew member will come get you. Do not climb the gate.
- Check your email
90% of sails leave from Monroe, but occasionally we use Burnham, DuSable, or Montrose. Your confirmation has the exact location.
Sailing on the catamaran Latitude Adjustment? Use the charter directions instead.
Before you go
First-sail checklist.
Arrive early
Plan to be at the gate 15 minutes before your sail. The boat leaves on time.
Pack light
Soft-soled shoes, layers, sunscreen, water, and a windbreaker. Bring a towel if you plan to swim.
Check your email
Your confirmation and day-before reminder contain the boat, gate, and any weather updates.
Sign the waiver
Everyone completes a liability waiver before sailing. Parents may sign for children.
Schedule
When we sail.
Sails run May through October, seven days a week. Weekday evenings are the easiest to book; weekends fill first.
- Monday–Friday
- 6:30–9:30 PM
- Saturday–Sunday
- 10 AM, 1:30 PM, 5 PM
- Season
- May–October
- Typical duration
- 3 hours
Weather
The lake decides.
Weather on Lake Michigan is different from inland. If the captain cancels, you will be contacted at least two hours before your sail and can reschedule at no charge.
If you do not hear from us, the sail is on as scheduled. Check your schedule online or call the office if you are unsure.
Questions
First-visit questions.
What if I can't find the boat?
Wait at the Monroe Dock entrance and call the office. Your confirmation email also includes your skipper or crew contact for private cruises.
Is there parking at Monroe Harbor?
Parking is controlled by the City of Chicago and fills quickly on summer weekends. Try SpotHero for nearby garage deals, or take a rideshare to 400 E Monroe St.
Can I change my sail date?
Yes, with at least 48 hours' notice there is no penalty. Less than 48 hours or a no-show can result in loss of sail time or a $50 rescheduling fee. Private cruises forfeit the sail. See policies.
What should I do before my first lesson?
Complete the 2-minute student survey and take the beginner quiz. It helps us customize your lesson.
Do I need to print anything?
No. Your confirmation email is enough. Bring a phone with the email handy in case you need the gate or boat details.
See you at the gate
Ready for your first sail?
Book online, check your email, and meet us at Monroe Harbor. We will take it from there.