Wanted: Deckhand/educators for 2021 sailing season
Seasonal, starting January 1970
Posted by: Windy of Chicago, LTD on February 2, 2021
Category: Deck: Unlicensed

Position dates:   May 16- late September.  Shorter contracts may be available.  Windy conducts day sails, charters, educational field trips, corporate and private events on Chicago’s coastline.  Some day sails and educational tours will require crew to do historical and nautically-themed storytelling, and conduct Tall Ship Sail Training for youth and adults, covering Tall Ship lore, history and skills.  Applicants need to have interest in oral presentation, teaching, and must be highly motivated to engage guests and students in these experiences.  Skills in oral communication, and customer service, theatre arts, and/or performance, are desirable but not required.  Individuals who wish to be “cross trained” in customer service roles and/or bartending (if over 21), are also welcome and compensated accordingly.  Motivated novices to sailing who are interested in traditional maritime life are welcome to apply.  Liveaboard privileges may be available. This position is a USCG safety-sensitive deckhand position and crew will be trained in the relevant required sailing skills and crew responsibilities.

Send a letter of interest and resume to Captain Bruce Randall at


Required certifications:
License: None, Inland
Medical: CPR

Commensurate with experience



Flag: United States of America
Rig: Schooner
Homeport: Chicago, IL
Sparred Length: 148'
LOA: 109'
LWL: 95'
Draft: 8' 6
Beam: 25'
Rig height: 85'
Freeboard: 8'
Sail Area: 4839 square feet
Tons: 93
Hull: Steel
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