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Offshore Sailing School Employment Opportunities

Current available positions are listed below. You may download our Application for Employment here. When completed, please send to the contact person listed for each position. Send all instructor applications to: and


This Southwest Florida position is based in Ft. Myers with management responsibilities for three resort based Offshore Sailing School operations on Captiva Island, Ft. Myers Beach and in St. Petersburg. We are seeking an experienced marine industry professional with strong cruising and racing skills and proven managerial history, who enjoys a challenging, fast-paced environment. Working closely with the Director of Operations, the Florida Regional Manager must possess the skills and knowledge to teach at all Offshore’s course levels. This position is for an effective team player and self-starter, with excellent communication and organizational skills, as well as seamless facility with Internet, and Microsoft Office systems.

On-site management responsibilities include:

  • Insuring all faculty members and maintenance personnel support the Company’s brand image, service and safety standards
  • Instructor testing, training, scheduling, supervision and evaluations
  • Client interaction to insure they get the best experience from America’s #1 Sailing School®
  • Overseeing and maintaining, to the highest level, the conditions of our large fleet of boats
  • Communicating with Company management and sales team to facilitate growth and meet sales targets at each base
  • Scheduling resources and preparing payroll reports, working with the Director of Operations on monthly budget plans and hitting those goals

This rewarding position has just become available, with the impending departure of a long time manager who is changing his life pursuits. Send your sailing and general employment resumes to Director of Operations Rob Brooks, Please also include a cover letter highlighting why you are the right person for this position.


We welcome inquiries for teaching positions at our seven locations in Florida, the British Virgin Islands, and New York Harbor. Instructor candidates must have excellent sailing knowledge and experience, ability to communicate that knowledge to clients, humility, patience and be team players. This rewarding position requires excellent “people” skills, strong teaching experience on keelboats and cruising sail and power yachts. All Offshore Sailing School instructors must be US Sailing certified at the Basic Keelboat level or higher (or at time of hiring have the skills to pass these levels quickly), and hold a USCG license or have the experience to obtain one at the appropriate level.

Candidates who wish to work in the United States must be U.S. citizens or carry a valid green card. Those who wish to work in the British Virgin Islands must have a valid work permit for that region. It takes several months to apply for and get a work permit, preference is given to those who are already able to work in the islands. Send your sailing resume and cover letter highlighting all aspects of your work experience to Director of Operations Rob Brooks,


We have a full time sales associate position available at our Ft. Myers, Florida headquarters. This position requires sailing experience and a passion for sailing or a strong desire to learn to sail. The right candidate will have a proven track record in sales and a commitment to achieving individual and company sales goals, plus excellent oral and written communication skills, ability to quickly adapt to company’s reservations software and work with multiple customers at the same time. A college degree is preferred. You will be communicating with highly educated, successful clients. Our products are fun to sell. Leads are hot, emanating from direct response to marketing efforts. Compensation includes base pay and commission. Send resume and cover letter highlighting the three most important reasons why you are the right person for a sales position to Director of Sales and Marketing Beth Oliver,


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