SOLD OUT. All sailing sessions are now fully booked.
LEARN TO SAIL - RIGHT ON THE WATER
Hands-on sailing lessons at Burnham Harbor during the Windy City Boat & Yacht Show
Start Sailing Now, presented by Sail America and SailTime, quickly became one of the most anticipated experiences at the Windy City Boat & Yacht Show. Due to high demand, all sessions are now fully booked.
Led by a certified captain, this on-water sailing experience introduces participants to essential sailing skills through immersive, small-group instruction right on the show grounds.
Your experience begins with a 60-minute classroom session covering the basics of sailing before heading out onto Lake Michigan for a 90-minute sail led by a certified captain - all set against the backdrop of downtown Chicago.
With no more than six participants per boat, each session offers a personal, interactive experience where you’ll learn the ropes, build confidence, and take the helm yourself.
Whether you’re trying sailing for the first time or finally checking it off your bucket list, this is the perfect opportunity to experience Chicago from a whole new perspective.
EVENT DETAILS
- Dates: Friday, June 12-Sunday, June 14
- Session Times: 10:00AM, 12:00PM, 2:00PM, & 4:00PM (4:00PM session not available Sunday)
- Status: SOLD OUT
- All sailing sessions for the 2026 Windy City Boat & Yacht Show are fully booked.
This program is presented by Sail America in partnership with SailTime, is supported by Yanmar and American Sailing, and it’s part of a broader effort to welcome new people into sailing in an approachable, enjoyable way.
All workshop participants will receive a complimentary sailing book courtesy of American Sailing. Attendees can easily redeem their free book through a digital postcard provided at the event.
We also extend our thanks to Spinlock for outfitting participants with premium deck vests for use throughout the weekend and for providing attendee goodie bags.
Hope to see you there!
QUICK DETAILS
What to Expect:
- 1-hour introduction + 1.5-hour on-the-water sailing experience
- Led by a certified captain
- Small groups (max. 6 participants per boat)
- Hands-on and beginner-friendly
Session Times:
- 10:00AM – 12:30PM
- 12:00PM – 2:30PM
- 2:00PM – 4:30PM
- 4:00PM – 6:30PM (not available on Sunday)
Dates & Location:
- All three days of the show (June 12-14, 2026)
- Onsite at Burnham Harbor
Pricing:
- $89 per person
- Includes same-day show admission
Registration:
- Advance registration is required.
- Select your session at time of purchase
- All sessions sold out.
Requirements:
- Participants must be 13+
- A signed waiver is required prior to boarding.
*All sailing sessions are now sold out.
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Produced by Informa - the leader in event management and organizer of seven U.S. International Boat Shows - this is your official gateway to the ultimate boating experience.
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