Skipper Connection

Meet New Friends & Expand You Sailing Network

Skipper Connection is the fun , economical  way for sailors to experience the social side of sailing.  And it is easy! Participating sailors join the Skipper Connection proprietary crew list, then simply 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!  There are no hidden costs, but a good crew/guest always provides some tasty refreshments or snacks.  Skipper Connection is the perfect recipe for sailing and friendships.

Additional Skipper Connection Benefits:

  • Exclusive forum access for qualified skippers and crew.
  • Unlimited sailing with a wide variety of vessels and skippers.
  • Discounted group sailboat rentals.
  • Discounts on sailing lessons.
  • Free annual J22 check-out.
  • Discounted check-outs on larger vessels.
  • Free participation for each of your first-time guests.

Join Skipper Connection today and enjoy a memorable season of fun with new friends. Skipper Connection uses a private Facebook group as a platform for conversation. Users must have a Facebook account in order to participate.


Introductory 2018–  $75.00

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!