Sailing Instructor

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!