Senior Instructor

Job Posted 11/25/2025
Falmouth Harbor Sailing School
290 Clinton Avenue PO Box 182
Falmouth, MA 02541
United States
Summer Only
Summer Only
Experience Required
Housing Provided
No
Industry
Instructor
Job Start Date
6/15/2026
Job End Date
8/15/2026
Application Closing Date
3/14/2026
Pay
$18.00 to $28.00 Per Hour
Job Description

Falmouth Harbor Sailing School is seeking Senior Instructors to join our summer team on beautiful Vineyard Sound. FHSS is a small, community-focused nonprofit that introduces over 300 young sailors each summer to seamanship, ocean stewardship, and the joy of being on the water. We serve students ages 7–18, from complete beginners to advanced racers, and our goal is to provide engaging, fun, and safe instruction that keeps sailors coming back year after year.

Senior Instructors are responsible for leading at least one class throughout the eight-week season, including developing lesson plans, running daily meetings, and creating a positive learning environment on and off the water. Classes include Learn to Sail, Opti 1 and 2, 420 1 and 2, and Adventure Boating, offering instructors the chance to work across a wide range of boats and experience levels. When not teaching your primary class, you will support other classes as needed.

Senior Instructors work closely with a tight-knit staff team and should be comfortable collaborating with peers, mentoring younger instructors, and communicating with parents. Responsibilities also include maintaining FHSS boats and equipment, practicing safe and effective powerboat operation, and helping prepare the sailing school before and after the eight-week program. With our boats launching at the mouth of Falmouth Harbor and quick access to the open waters of Vineyard Sound, FHSS offers some of the best teaching conditions on Cape Cod.

Job Requirements
  • Valid US Sailing Level 1 Instructor certification
  • CPR and First Aid certification valid through at least September 1, 2026
  • Experience working with children ages 7–18, ideally in a sailing or outdoor education setting
  • Strong sailing skills in dinghies and small keelboats
  • Confidence operating a motorboat while coaching beginner and intermediate sailors
  • Ability to develop lesson plans and run daily class sessions independently
  • Professionalism in communicating with students, parents, and fellow staff
  • Willingness to collaborate with a small, supportive team and contribute to the FHSS community
  • Availability for the full program dates: June 15 to August 15, 2026
  • Time commitment of approximately 40 hours per week, Monday through Friday (8:00 AM to 5:00 PM, with flexibility in afternoons).
  • Approval of the FHSS Board of Directors
Employer

290 Clinton Avenue PO Box 182
Falmouth MA 02541
United States
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