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Career Sailing School Instructor Opportunities

Are you thinking about a sailing career? Offshore Sailing School often has openings at its Florida and British Virgin Islands branches for qualified women and men who can teach sailing courses from Basic Keelboat to Offshore Passage Making. In addition, from time to time, branch management opportunities become available for sailors with expert sailing instruction, organizational and leadership skills, and sailboat and powerboat maintenance experience.

Evaluation of Your Ability to Become a Sailing School Instructor

If you love to sail and have the sailing instructor experience, or the talent, experience and knowledge to become a sailing instructor, we want to talk to you!

Sailing on a flotilla in vast blue waters


Learn the “Right” Way to Teach Sailing

America’s #1 Sailing School is owned and operated by National Sailing Hall of Fame Honorees, Steve Colgate (2015), and Doris Colgate (2022). The Offshore Sailing School team of US Sailing Certified Instructors are ready to help you become a sailing instructor or powerboat instructor. The first step is to submit your sailing resume to:

Josh Julow, Director of Operations

Experience and traits we look for include:

  • Sailing, cruising and (preferably) racing experience as skipper and crew on boats over 20′
  • Coaching or teaching sailing experience, but also any non-sailing teaching experience
  • A calm, caring personality that also includes patience and humility
  • US Coast Guard License level achieved or the sailing experience required to obtain one
  • US Sailing and/or ASA, RYA, Sail Canada instructor certifications achieved

US Sailing Instructor Evaluation Certification

Brothers on a yacht

When hired, if you do not already have US Sailing Instructor certifications, you will be placed in a 3-day comprehensive US Sailing Basic Keelboat Instructor Certification Evaluation first, as soon as possible. Passing this evaluation must be accomplished within a year of your initial employment date. This instructor certification and achieving the US Sailing Bareboat Cruising Instructor Certification are a pre-requisite to remain and advance in Offshore Sailing School’s faculty.

Offshore Sailing School’s Commitment to You and Your Commitment to Offshore Sailing School

If you are hired and commit to a 12-month period as a full-time instructor for Offshore Sailing School, the fee for each US Sailing Instructor Certification level you pass will be reimbursed by Offshore Sailing School. In addition, travel costs to relocate will be considered but are not guaranteed.