Sharpen your skills, learn about strategy, and meet new friends in a low key racing environment.

Wednesday night racing

Monroe Harbor

Sail Chicago is committed to sailing instruction, and our racing program is a natural extension of our class offerings. We offer weekly Wednesday night windward-leeward racing throughout the season, challenging skippers and crew to optimize speed and performance. Racers work with spinnakers, learning how to properly rig, hoist, trim, and douse them.

Sail Chicago Racing is a blend of camaraderie, learning, team-building, and friendly competition. After the races, teams gather at Columbia Yacht Club — our Wednesday night sponsor.

Required: Level 1: Crew Class

Cost: $100 per season

racing season ticket

racing tiller times

Racing Tiller Times offer an opportunity to fine-tune racing skills outside of a competitive setting. Experienced skippers, foredeck specialists, and seasoned racers are on hand to answer questions.

Cost: free for racers with a season ticket

weekend REGATTAS

Sail Chicago fields boats for several regattas in the Chicago area, offering opportunities for longer racing distances and practice with starting sequences. In recent years, we have participated with multiple boats in the Verve Cup Inshore Regatta (late August) and the Rainbow Regatta (July). Plans are underway to add Columbia Yacht Club's Colors Regatta in 2026.

Cost: not included

FREQUENTLY ASKED QUESTIONS

  • Yes, anyone who has completed Sail Chicago's Level 1: Crew class is welcome. Many students develop time at the helm and more confidence by racing.

  • That's totally fine. Most aren't able to during the summer. You will be allowed to sign-up weekly. An email is sent typically on Sunday morning for the upcoming Wednesday race.

    For more information use the Racing channel on the Slack Page.

  • Sail Chicago uses its Colgate 26 fleet for racing.

  • No problem! Every boat includes at least one experienced foredeck crew member and a racing skipper. We'll be happy to introduce you to the thrill of correctly rigging, safely hoisting, trimming, and dousing the spinnaker.

  • In order to make for a safe and enjoyable experience for everyone, we do require that racers have completed Sail Chicago’s Level 1: Crew class and/or have the equivalent experience. Please see the the Instruction page for a list of skills that students in each class are expected to have acquired.

  • The cost is $100 to purchase a season ticket/pass which allows you to sign-up for weekly races.

  • Unfortunately, we are unable to accommodate visitors. As much as we like to meet people who share our passion for racing, our insurance coverage does not allow us to do this. Sorry!

  • Yes, we have Racing Tiller Times. These sessions cover topics such as the US Sailing Rules of Racing, roles/positions, spinnaker usage, starts, and general tactics.

  • Weekend races will offer longer racing distances and additional practice with racing starting sequences. These would be offered as private sails (not included in the $100 Wednesday night racing "season ticket").

  • In addition to Wednesday night racing, Sail Chicago fields boats in weekend regattas. For the past several years, we have participated with multiple boats in the Verve Inshore Regatta, held in late August, and we intend to add the COLORS regatta as well. Regatta participation is funded by participants and is not included in the $100 Wednesday night racing "season ticket."

  • You can purchase a "racing ticket" on the Racing page or on my.sailchicago.org under the "Courses and Classes" section of the Instruction tab. Look for the "Racing Season Membership" course.

  • It depends. We require the skills taught in Sail Chicago's Level 1: Crew class, though we understand those skills may have been acquired elsewhere. See our Instruction page for details on the skills needed. If you're still unsure, reach out to the Racing channel on the Sail Chicago Slack.

  • Yes, you need to be a current member in good standing to participate in our racing program.