Sailing Instructor

Paddle Boston; Stoneham (MA); On-site; USD 34,440 - 41,328; Part time

Benefits offered by this job

Flexible schedules

Free use of boats

Opportunity for additional hours

Job summary

Paddle Boston is seeking a dynamic Sailing Instructor for our Spot Pond location in Massachusetts. This role involves teaching sailing fundamentals to kids and adults while fostering a fun, safe environment. Candidates should have solid sailing experience and be available on weekends, with potential for year-round employment.

We offer competitive pay between $25 and $30/hour, flexible schedules, and the opportunity for additional hours as a dock hand or site supervisor. Enjoy free use of our boats and join a friendly team!

Qualifications

• Solid sailing experience and some weekend availability required.
• Must demonstrate reliability and good communication skills.
• Desirable to have experience in other paddle sports.

Responsibilities

• Teach sailing fundamentals to diverse groups.
• Lead instruction on sailboats, ensuring safety and engagement.
• Create a fun and enjoyable environment for all visitors.

Skills

Solid sailing experience

Friendly and outgoing personality

Experience working with kids

Instructor certifications

Education

CPR/First Aid Certification

MA Boating Safety Course or NASBLA Certificate

Job description

Now Hiring: Sailing Instructor – Paddle Boston (Spot Pond)

Come join our team if you love being outdoors and want to share your passion for the water with others!

Paddle Boston offers a relaxed outdoor work environment with competitive pay and benefits. We are currently looking for a dynamic and engaging Sailing Instructor to lead small classes and private lessons at our Spot Pond location. Beyond the summer season, this role offers the potential for year-round employment opportunities in concert with Weston Ski Track and Community Skating @ Kendall Square.

What You’ll Be Doing

• Teaching diverse groups of kids and adults the fundamentals of sailing.
• Leading instruction in our fleet of Cape Cod Mercury 14 sailboats, as well as one RS Cat.
• Creating a fun, safe, and engaging environment for all our visitors.

What We’re Looking For

• Required: Solid sailing experience and some weekend availability.
• Required: A friendly, outgoing, dynamic, and engaging personality.
• Reliability: Lessons are scheduled through the summer and fall so reliability and communication is a must!
• Desirable: Experience working with kids or a background in other paddle sports (kayaking, canoeing).
• Desirable: Instructor certifications, CPR/First Aid, and MA Boating Safety Course (or NASBLA Certificate). Note: Training is available for the right candidate!

Compensation & Perks

• Pay Rate: $25–$30/hour + tips (based on experience).
• Flexible Schedules: Opportunities for both full-time and part-time work are available.
• More Hours Available: Need a steadier schedule? We can offer additional hours working as a dock hand or site supervisor through the summer and into the fall.
• Free use of our boats: staff enjoy the perks of free paddling and use of the sailboats (subject to availability).
• Start Date: As soon as possible!