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Head Sailing Instructor Jobs in Illinois (NOW HIRING)

Lake Forest

Sailing Instructor

Lake Forest, IL

$16/hr

Summer Sailing Assistants will work from 8:30am-4:00pm Monday to Friday, June 8th - August 7th. ... Head Coach and Race Coaches Ensure camper safety and enforce safety protocols Rig, launch, and ...

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Head Sailing Instructor information

See Illinois salary details

$7

$16

$23

How much do head sailing instructor jobs pay per hour?

As of May 27, 2026, the average hourly pay for head sailing instructor in Illinois is $16.43, according to ZipRecruiter salary data. Most workers in this role earn between $15.38 and $18.17 per hour, depending on experience, location, and employer.

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

To thrive as a Head Sailing Instructor, you need advanced sailing proficiency, teaching experience, and relevant instructor certifications such as US Sailing or RYA qualifications. Familiarity with safety protocols, fleet management systems, and maintenance tools is crucial. Leadership, strong communication, and problem-solving skills help you effectively guide teams and foster a positive learning environment. These skills ensure safe, efficient operation of sailing programs and high-quality instruction for all participants.

What are some common challenges faced by a Head Sailing Instructor, and how can they be managed?

As a Head Sailing Instructor, you'll often need to balance administrative responsibilities with hands-on teaching, which can be challenging during peak sailing seasons. Managing diverse skill levels among students, ensuring safety standards, and coordinating with other instructors require strong organizational and communication skills. Proactive planning, clear delegation, and regular team briefings can help manage these demands while maintaining a positive learning environment. Building strong relationships with your team and keeping up with the latest safety protocols are also essential for success in this role.

What are Head Sailing Instructors?

Head Sailing Instructors are experienced professionals responsible for overseeing sailing programs, managing instructional staff, and ensuring the safety and skill development of participants. They design lesson plans, coordinate training sessions, and maintain sailing equipment. Additionally, Head Sailing Instructors often mentor junior instructors and serve as the primary point of contact for students and parents regarding sailing instruction. Their leadership ensures a high-quality and safe learning environment for all involved.

What is the difference between Head Sailing Instructor vs Sailing Instructor?

AspectHead Sailing InstructorSailing Instructor
CertificationsRequired sailing certifications, CPR, first aidSame certifications often required
Work EnvironmentLeads sailing programs, manages staffTeaches sailing skills, assists in lessons
ResponsibilitiesProgram planning, staff supervisionDirect instruction, student coaching

The main difference is that the Head Sailing Instructor oversees the entire sailing program and manages staff, while the Sailing Instructor focuses on teaching students sailing skills. Both roles require similar certifications and work in the same environment, but the Head Sailing Instructor has additional leadership responsibilities.

What are the most commonly searched types of Sailing Instructor jobs in Illinois? The most popular types of Sailing Instructor jobs in Illinois are:
What are popular job titles related to Head Sailing Instructor jobs in Illinois? For Head Sailing Instructor jobs in Illinois, the most frequently searched job titles are:
What job categories do people searching Head Sailing Instructor jobs in Illinois look for? The top searched job categories for Head Sailing Instructor jobs in Illinois are:
Head Sailing Instructor jobs near you

Sailing Instructor

City of Lake Forest, IL

Lake Forest, IL • On-site

$16/hr

Temporary

Posted 6 days ago

Job description

Salary: $16.00 Hourly
Location : Recreation Center; 400 Hastings Rd, Lake Forest, IL
Job Type: Temporary
Department: Recreation Department
Opening Date: 01/22/2026
Description
The City of Lake Forest is looking for staff to work within the sailing program for the Lake Forest Park Beach 2026 season. Summer Sailing Assistants will work from 8:30am-4:00pm Monday to Friday, June 8th - August 7th.
Examples of Duties
  • Enforces all facility policies, rules and regulations to ensure the safety of program participants both on and off the water
  • Maintain a fun and productive learning environment
  • Teach basic to intermediate sailing skills
  • Drive and operate coach boat during on-water instruction
  • Follow instruction and guidance from Head Coach and Race Coaches
  • Ensure camper safety and enforce safety protocols
  • Rig, launch, and maintain boats and equipment
  • Supervise and engage campers in a positive, supportive environment
  • Other duties as assigned

TRAINING INFORMATION:
On-Site: Times and Dates TBD - likely week commencing May 25th or June 1st
*All Training is MANDATORY. CPR Training will be offered.
Qualifications
USA Sailing Level 1 Coaching Certificate
CPR Qualified (CPR Training will be coordinated)
IL state NASBLA boater's license
Supplemental Information
Working at the Lake Forest Recreation Department this summer offers many benefits beyond just a paycheck. You're not just getting a job-you're joining a community and gaining access to unique perks that make your summer healthier, more enjoyable, and memorable!
Bonus Benefits:
Free Lake Forest Fitness Center Membership Stay active and healthy during the summer without extra financial commitment!
  • Enjoy unlimited access to our well-equipped fitness center, and save money while prioritizing your health and fitness.
  • Discounts on group exercise classes and personal training sessions.

Free Paddle Board and Kayak Rentals at the Boating Center Perfect for adventure seekers and nature lovers!
  • Explore Lake Michigan in a kayak or on a paddleboard at no cost.

Discounted Rates at Deerpath Golf Course Nothing beats golf at Deerpath in the summer!
  • Play a round of golf at Deerpath Golf Course at a rate of $32 for 18 holes or $27 for 9 holes.
  • Enjoy a 15% discount on purchases at the Pro Shop.

Don't miss this excellent opportunity to get paid and gain experience while spending your summer outdoors in Lake Forest.
The City of Lake Forest is an equal opportunity employer and does not discriminate based on race, religion, disability, age, ethnicity, national origin, sex, gender, LGBTQ identification, family status, or military status.
Women and minorities are strongly encouraged to apply.
Apply online at CityofLakeForest.com
No benefits are associated with this position.

Apply