Cruising Sail Fleet

The Cruising Sail Fleet is an active fleet of sailors interested in cruising, whether it be to ports on Lake Michigan and all of the Great Lakes, to distant ports of call (some have been to the Caribbean and around the world) or just local cruising with family and friends.  The Fleet manages an active schedule of events throughout the year, both on and off the water, such as:  weekend cruises to other Lake Michigan Harbors, rendezvous at more distant destinations, educational seminars of interests to beginner and more experienced cruisers, dock parties and navigational events on the water, and off-season social events.  The Fleet welcomes all members to share the knowledge and fun of cruising under sail -- in Chicago and at other interesting destinations.

The Cruising Sail Fleet hosts a variety of events throughout the year that typically include:
  • Dancing with the CSF Stars
  • Night at the Lanes
  • Meet The Fleet Dinner
  • Winter Caribbean Cruise
  • Spring Ball
  • Dock Party With Bilge Auction
  • Spring Cruise
  • Cruise to Racine
  • Summer Cruise to Holland
  • Labor Day Cruise to New Buffalon, Michigan
  • Awards/Recognition Dinner


The Chicago Yacht Club has achieved international recognition by hosting important competitive events for our active Power Fleet. For example, the Fleet competes against various Chicago yacht clubs in twelve predicted log contests throughout the year that challenge our power boaters’ navigational skills. In addition, the Club has hosted the North American Cruiser Association’s North American Invitational Championships (NAI) in the past. Above and beyond the camaraderie the Fleet enjoys at cruises and dock parties, they also share a commitment to civic duty for the City of Chicago and host several charitable events each year, such as hosting summer cruises for the developmental disabled and the sight impaired.  In addition, the Fleet hosts a summer camp day for the Chicago Park District.

The Power Fleet schedule of events typically includes:

  • Belmont Opener 
  • Spring Cruise 
  • Fleet Review
  • Special Needs Cruise
  • Sight Impaired Cruise
  • Annual Cruise
  • Mackinac Race Press Boat Coverage
  • Annual Dock Party
  • Fall Cruise


The races for the Offshore and One-Design Fleets define competitive sailing in Chicago. The Club’s Offshore calendar highlights include the annual Race to Mackinac, the National Offshore One-Design Regatta (NOOD), the Verve Cup, and the North American Challenge Cup for sailors with disabilities. The Club holds popular Wednesday night races at both stations every week from May through September. Every year we are honored to host a variety of North American Championships and on occasion, World Championships.


Over the years, the Chicago Yacht Club has been the home of World & Olympic Champions, Collegiate All-Americans & Americas Cup veterans.

CYC has the most extensive offering for sailboat racing in the Midwest.  Whether you are a casual racer or hard-core, a beginner or seasoned professional, or if you are looking to race dinghies or keelboats around the buoys, or long distance, CYC can provide you the most opportunity to enjoy the sport.

On Lake Michigan you will find boats of many classes, from Volvo 70s, TP52s, and Farr 40s to the every popular J/105s, Sydney 38s, and Beneteau 40.7s.

Belmont Station is CYC’s center for small boat and one-design sailing and instruction.  Programs include: 

  • Spring and fall frostbiting in 420s, Sonars, V15s and J/70s. 
  • Summer One-Design racing includes Luders 16, Shields, Etchells, J/70, Tartan 10, Beneteau 36.7, and J/111 classes
  • Private and group lessons on racing, specialty clinics and US Sailing Keelboat Certification courses 

During the summer season, CYC hosts three of the largest offshore regattas in North America including:

  •  The Chicago Yacht Club Race to Mackinac
  •   Sailing World NOOD Regatta
  • Verve Cup Regatta
  • Cruising class racing is offered at CYC offshore events
  • Wednesday evening casual Skyline racing is offered at both stations throughout the summer