Chicago's #1 learn-to-sail program
Start with one sail. Stay for the season.
Three‑hour lessons, seven days a week, May through October. No experience required — our USCG-licensed captains meet you where you are and get you on the helm.
The first step
Test the waters.
Buy one three‑hour sail for $300 and get three more free. It is the lowest-pressure way to find out whether sailing fits — and every hour counts toward certification.
- Four sails for the price of one
One paid 3‑hour sail plus three free sails. Free sails expire at the end of the season.
- No long-term commitment
Sail first. Decide about a membership after you have met the crew and the boats.
- Share it with a partner
The Couple's Package includes two paid sails and six free sails, and can be shared.
- Certification credit
All seatime counts toward NauticEd and SLC certifications.
Trial membership
Choose your first package.
Both options include three‑hour sails on monohulls and our 38' catamaran, scheduled online around your calendar.
Single's Package
Buy one 3‑hour sail, get three free
- Four 3‑hour sails total
- Flexible online scheduling
- All seatime counts toward certification
- Weeknight and weekend sails
Couple's Package
Buy two 3‑hour sails, get six free
- Eight 3‑hour sails total
- Shareable with a partner or friend
- Each sailor registers separately
- All seatime counts toward certification
Single 3‑hour sail also available for $75 with promo code SingleTrial. Free sails expire at the end of the season.
On the water
What you'll learn.
Lessons are hands-on from the first minute. You will rotate through crew positions, take the helm, and leave with skills you can use on any boat.
Sailing basics
Points of sail, sail trim, tacking, gybing, and how to read the wind on Lake Michigan.
Boat systems & rigging
Rigging, knots, engine checks, and the systems that keep a boat moving and safe.
Safety & emergencies
Man-overboard drills, VHF basics, weather awareness, and emergency procedures.
Navigation
Charts, marks, GPS, and plotting — including river trips and lock navigation.
Docking & anchoring
Slip departures and returns, spring lines, anchoring, and boat handling under power.
Boat-owner prep
For future owners: what to look for, how to maintain a boat, and how to build seatime.
Lesson formats
Group, private, or catamaran.
Most sailors start in a group lesson and move into club sails. If you want focused instruction or a specific boat, we can build that too.
- Group lessons
Three hours, up to six sailors, mixed experience levels. The social way to learn.
- Private lessons
Up to six people, three‑hour minimum, tailored to your goals. Beginners welcome.
- Catamaran lessons
Train on our 38' Lagoon catamaran and add a catamaran endorsement to your sailing resume.
Schedule
Three hours on the lake.
Sails run seven days a week, May through October. Book online; your confirmation email includes the boat and gate assignment.
- Monday–Friday
- 6:30–9:30 PM
- Saturday–Sunday
- 10 AM, 1:30 PM, 5 PM
- Season
- May–October
- Meeting point
- Monroe Harbor (most sails)
After you purchase
Complete the 2-minute survey
Tell us about your goals so we can match you with the right boat and captain.
Take the beginner test
Start the beginner quiz — no pressure, it just helps you get oriented.
Schedule your sails
Pick your dates online, then watch for the confirmation and reminder emails.
Packages
More sails, better value.
If you already know you will sail more than four times, a sail package is the simplest next step. All packages are good for two years.
Port Package
One sail
- One 3‑hour sail
- Good for two years
- Weeknight and weekend availability
- Monohulls and catamaran
Lighthouse Package
Five sails
- Five 3‑hour sails
- Good for two years
- Weeknight and weekend availability
- Monohulls and catamaran
Explorer Package
Ten sails
- Ten 3‑hour sails
- Good for two years
- Weeknight and weekend availability
- Monohulls and catamaran
Good to know
Questions, answered.
Do I need any sailing experience?
No. Most people who sail with 3rd Coast are complete beginners. Captains teach to the level of the group and you can repeat lessons until you feel confident.
What should I bring?
Soft-soled shoes, layers, sunscreen, water, and a windbreaker. You can bring snacks and drinks on private cruises; check your confirmation email for specifics.
What happens if the weather turns?
The captain decides. If we cancel for weather, you will be notified at least two hours before your sail and can reschedule at no charge. See the cancellation and weather policy.
Can I bring a guest?
Yes. Guests need their own account and registration. If your package is shareable, schedule yourself, log out, then schedule your guest with their own email. The Trial Membership is a good option for a guest.
Where do lessons leave from?
Most sails leave from Monroe Harbor at 400 E Monroe St (approximately). Occasionally we use Burnham, DuSable, or Montrose. Your confirmation email always has the exact location — check it before you leave. See Plan Your Visit.
Is there an age limit?
There is no age minimum for private lessons. For group lessons and club sails, contact the office so we can match you with the right boat and crew.
Ready when you are
Get on the water this season.
Buy the Trial Membership, pick a date, and we will handle the rest. Questions? Call or email — a real person answers.