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Seasonal Sailing Instructor Jobs in Chicago, IL (NOW HIRING)

This is a part-time seasonal position that typically requires working up to 30 hours per week. The instructor is expected to be available during the entire sailing class season, working mid-June ...

This is a part-time seasonal position that typically requires working up to 30 hours per week. The instructor is expected to be available during the entire sailing class season, working mid-June ...

Beach Director-Seasonal

Crystal Lake, IL · On-site

$39.80K - $51.90K/yr

... sailing lessons, and special events. Serving as the primary point of contact for beach-related ... You'll also step in as needed to support Beach Managers, Swim Lesson Instructors, or Lifeguards ...

Seasonal Sailing Instructor information

See Chicago, IL salary details

$7

$17

$24

How much do seasonal sailing instructor jobs pay per hour?

As of May 28, 2026, the average hourly pay for seasonal sailing instructor in Chicago, IL is $17.47, according to ZipRecruiter salary data. Most workers in this role earn between $16.35 and $19.33 per hour, depending on experience, location, and employer.

What are the key skills and qualifications needed to thrive as a Seasonal Sailing Instructor, and why are they important?

To thrive as a Seasonal Sailing Instructor, you need solid sailing knowledge, safety awareness, and typically certifications such as US Sailing or ASA Instructor credentials. Familiarity with sailboats, rescue boats, VHF radios, and first aid equipment is essential. Strong communication, patience, and the ability to motivate and instruct diverse age groups are standout soft skills. These qualifications and skills are crucial for ensuring student safety, effective teaching, and a positive learning environment on the water.

What are some common challenges faced by seasonal sailing instructors, and how can they be managed effectively?

Seasonal sailing instructors often encounter challenges such as adapting lesson plans to varying weather conditions, addressing the diverse skill levels of students, and maintaining safety on the water. Effective communication, flexibility, and strong situational awareness are key to overcoming these challenges. Successful instructors often collaborate closely with other staff to ensure smooth operations and may participate in ongoing training to stay current with best practices in safety and instruction.

What are seasonal sailing instructors?

Seasonal sailing instructors are professionals hired for a specific period, typically during the warmer months, to teach individuals or groups how to sail. They work at sailing schools, camps, or clubs, instructing students on sailing techniques, safety procedures, and boat handling. Their responsibilities include planning lessons, demonstrating maneuvers, supervising on-water activities, and ensuring a safe learning environment. This role requires strong sailing skills, teaching ability, and certifications such as those from the American Sailing Association or U.S. Sailing. Seasonal sailing instructors play a crucial role in helping people develop confidence and competence on the water.

What is the difference between Seasonal Sailing Instructor vs Sailing Coach?

AspectSeasonal Sailing InstructorSailing Coach
CertificationsCPR, First Aid, Sailing Certifications (e.g., US Sailing Certification)Similar certifications, often including advanced coaching credentials
Work EnvironmentSummer camps, sailing schools, recreational programsPrivate lessons, competitive teams, sailing clubs
Employer & IndustryRecreational and educational sailing programsCompetitive sailing teams, sailing academies

The main difference is that a Seasonal Sailing Instructor typically teaches sailing basics to groups or individuals during specific seasons, focusing on safety and foundational skills. A Sailing Coach often works with competitive sailors, providing advanced training and strategy. Both roles require similar certifications and work in sailing environments, but their focus and target audiences differ.

What are the most commonly searched types of Sailing Instructor jobs in Chicago, IL? The most popular types of Sailing Instructor jobs in Chicago, IL are:
What job categories do people searching Seasonal Sailing Instructor jobs in Chicago, IL look for? The top searched job categories for Seasonal Sailing Instructor jobs in Chicago, IL are:
What cities near Chicago, IL are hiring for Seasonal Sailing Instructor jobs? Cities near Chicago, IL with the most Seasonal Sailing Instructor job openings:
Sailing Instructor

Other

Posted 19 days ago


Job description

Spend your summer making memories and making an impact! The Glencoe Park District is a nationally accredited, Gold Medal Award-winning agency that offers fun and rewarding seasonal jobs opportunities. Join our team this summer and gain hands-on experience, build transferable skills, make new friends, and create lasting memories for Glencoe families!


Job Summary:

Under the immediate supervision of the Facility Manager, the Sailing Instructor is responsible for performing various duties to prepare the beach for the customers' demands. The Instructor also assists with the daily sailing lesson operations and rental hut.


The Sailing Instructor is responsible for performing the duties outlined below. This is a part-time seasonal position that typically requires working up to 30 hours per week. The instructor is expected to be available during the entire sailing class season, working mid-June through mid-August.


Qualifications:

  • Must be at least 18 years old or older.
  • Must possess a valid Driver's Licenses and have a good driving record.
  • 1-2 years of sailing experience from an accredited sailing program.
  • Knowledge of advanced sailing maneuvers and ability to teach 5-10 participants at a time during a class.
  • Must possess CPR/AED/First Aid certification or willing to obtain within one month of hire.
  • Must possess a valid L. Boating Licenses.
  • U.S. Sailing Instructor Certification.
  • Must pass the Glencoe Park District Boat Training.
  • All employees must pass a criminal background check, which the Glencoe Park District will cover.


Required Knowledge:

  • Knowledge of public recreation philosophy with strong communication skills
  • Proven technical understanding related to the role


Required Skills:

  • Dependable and flexible, with strong safety awareness and sound judgment
  • Ability to understand and follow rules and instructions
  • Ability to read, write, and organize materials


Essential Duties and Responsibilities:

Instruct Sailing Programs

  • Work in a team with a particular lesson group (Beginner, Intermediate, Intro to Racing).
  • Coordinate and be the primary contact for all sail lesson programs such as Beginner/Intermediate/ Intro to Racing while coordinating all park district sailing classes.
  • Help develop a season lesson plan.
  • Keep attendance at all sailing programs and communicate with parents for any cancellations or issues regarding any sailing-related activities.
  • Help write daily lesson logs.
  • Must communicate with the Facility Manager regarding safety issues involving the park district sailing fleet.
  • Will coordinate and schedule all sailing lessons staff schedules throughout the season.
  • Create certificates or awards for participants in sailing classes.
  • Programs should include:
    • Basic Sailing
    • Rowing and boat retrieval
    • Knot tying
    • Basic boat maintenance
    • Emphasis on sportsmanship and respectful behavior
    • Protocol for the rigging and de-rigging of boats
    • Introduction to racing tactics
    • Introduction to racing rules
    • Teaching following S. Sailing Instructor Guidelines.

Instruct Adult Sailing Classes

  • Help develop a season lesson plan.
  • Attend and coordinate all regattas; report results to Facility Manager.
  • Communicate effectively with sailing staff and other GPD staff.
  • Listen to and incorporate, if appropriate and beneficial, the ideas and suggestions of the other sailing staff members.
  • Communicate appropriately to beach/boat staff.
  • Will communicate with participants via email or phone call before, during, and after class.
  • Provide direction and feedback to the sailing program participants.
  • Communicate effectively regularly with the Facility Manager.
  • Accept direction and get approval from the Facility Manager while taking the initiative to offer ideas for developing and implementing a successful sailing program.
  • Engage and encourage junior sailors.
  • Maintain boats and areas used by sailing staff and program sailors.
  • Coordinate and assist in pre-season and post-season maintenance of sailing equipment.
  • Coordinate and assist in the maintenance of park district-owned sailing craft.
  • Ensure that boats are put away correctly.
  • Complete routine maintenance on all sailing fleets and weekly and pre-class inspections (missing clips, pins, etc.)
  • Promptly report all damages to boats to the Facility Manager.
  • Assist with boat cleaning when required.
  • The program area must be clear of related trash and gear by the end of the program day.
  • Cleaning up after themselves in any areas of the beach that are used.
  • Follow water safety procedures.
  • Practice safe use of boats according to Glencoe Park District policies.
  • Enforce Glencoe Park District boating rules following the policy.
  • Will coordinate all private lessons and communicate with sailing staff regarding all staff schedules during private lesson time.
  • Follow all safety policies and procedures of the Glencoe Park District.
  • Assisted in setting up and organizing sailing classes.
  • Field and answer patron questions to the best of their abilities.
  • Participate in "community activities" such as the 4th of July or any sailing-related special event activities.

Hours:

Due to the nature of Park District programming, evening, weekend, and some holiday hours are to be expected


The Facility Manager might also direct the Sailing Instructor to perform other assignments not included in this job description, which is subject to periodic review and revision.


The above statements are intended to describe the general nature and level of work the Sailing Instructor performs. They are not intended to list all responsibilities, duties, and requirements.


Pay Scale:

This is a seasonal part-time, non-exempt (hourly) position. The intended starting pay for this position is $25 per hour, with a full pay scale ranging from $25 per hour to $50 per hour.


Final compensation will be determined in good faith based on an evaluation of the candidate's qualifications, experience, and the recommendation of the (Hiring Manager), or the (Dept. Head).


Benefits Include:

  • Park District Membership
  • Program and Rental Discounts


*To review the full job description, please contact the hiring manager.


Glencoe Park District is an equal opportunity employer, and all qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity or expression, pregnancy, age, national origin, disability status, genetic information, protected veteran status, or any other characteristic protected by law. Those applicants requiring reasonable accommodation to the application/interview process should notify the human resource manager.