Meet Our Boats

  • Wind Whisper

    Uses: Basic Keelboat Classes and BK Certified Veteran Fun Sails

    Wind Whisper is an O'Day 240, which is 24 feet long. Wind Whisper is used to teach our Basic Keelboat Class and is sailed by our Veteran sailing students once they pass the class to continue to build camaraderie and improve their sailing skills. 

  • Rocking Horse

    Uses: Rental/Water BNB, Basic Cruising, and Bareboat Cruising Classes

    Rocking Horse is an Erickson 32 fixed keel sailboat formerly used as a racing boat before being acquired by WMSAIL for use in basic cruising, to teach our bareboat cruising classes, and use as a rental/water BNB.

  • Challenge 20

    Uses: Adaptive Sailing Classes focusing on disabled veterans

    Challenge 20 is a fixed keel sloop equipped with accessible sip/puff joystick equipment designed for people with varying mobility needs.

  • Da Doo Run Run (DDRR)

    Uses: Adaptive Sailing classes focusing on disabled veterans, Basic Keelboat classes, and cruises

    Da Doo Run Run (DDRR) is a Catalina 22 sloop used for adaptive sailing and to teach the US Sailing accredited entry level sailing class (Basic Keelboat Class). DDRR is one of the sailboats available to veterans to sail once they pass the Basic Keelboat Class.

  • Jabberwocky

    Uses: Basic Keelboat Class and Basic Keelboat Certified Veteran Fun sails

    JabberWocky is a Catalina 25 sloop used for veteran sailing after completion of the Basic Keelboat Class as well as for public cruising and Basic Keelboat Classes.

  • Wave Dancer

    Uses: Basic Cruising and Bareboat Cruising Classes

    Wave Dancer is a Sabre 36, sloop rig with a rich history being  involved sixteen Chicago to Mackinac Races, taking Second Place two times.  Wave Dancer is utilized for our many veteran focused cruises such as with the Motown Womens VA.