Skipper Connection



Skipper Connection is the fun way for sailors to experience the social side of sailing. Choose from a wide variety of opportunities that include economical sailing times and discounted services.  Skipper Connection is the perfect recipe for sailing and friendships.

It is fast and easy! Simply join the Skipper Connection private Facebook portal and post/respond to the ‘Skippers Looking for Crew’ forum postings. After you and the skipper have reached agreement, you are off for fun on the water!  While there are no hidden costs, you, as an appreciative crew, are expected to provides some appropriate refreshments.

Additional Skipper Connection Benefits:

  • Exclusive forum access for qualified skippers and crew.
  • No limits on sailing opportunities via ‘Skippers Looking for Crew’
  • Two discounted vessel sharing opportunities per month(<$10/hr).
  • Discounts on sailing lessons.
  • Free annual J22 check-out and discounts on larger vessel check-outs.
  • Free participation for each of your first-time guests.

Join Skipper Connection today and enjoy a memorable season of fun with new friends. Users must have a Facebook account in order to fully participate.

SKIPPER CONNECTION    $150/season (a savings of >$600.)

Pre-Season Special–  $115 (before April 15)

Skipper Connection is a forum to support the personal sailing activities of registered adult participants only.  Chicago Sailing, Incorporated (CS) acts solely as a facilitator, making no representations or guarantees. CS makes no decisions on participation, beyond basic qualifications of participants. CS makes no warranties of skills and takes no responsibility for activities between parties.  Inappropriate, illegal and commercial activities are strictly prohibited and grounds for immediate dismissal without refund.

Contact Us

Interested in expanding your sailing horizons? Let's make it happen! Drop us a line or give us a call so we can get your Skipper Connection membership started today!

Dock B, Belmont Harbor, Chicago IL 60657
(773) 871-7245

Say Hello!