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: Steve@OffshoreSailing.com and Rob@OffshoreSailing.com.


This career position is based at our largest branch location on Captiva Island, Florida – reporting directly to the Director of Operations. It requires travel to nearby headquarters in Ft. Myers, FL and to our four other branch locations as needed, while overseeing the operations of our largest teaching facility.  Skills and background required for this position include: Strong management resume; expert sailing knowledge and hands-on involvement in both cruising and racing; boat maintenance aptitude, expertise in coaching or teaching sailing, with willingness to attain US Sailing certification at the highest levels if not already in hand; proficiency in training the trainers to corporate standards. Please send your resume and sailing history with a cover letter highlighting why you are the right person for this position to Director of Operations Rob Brooks, Rob@OffshoreSailing.com, and Steve Colgate, Steve@OffshoreSailing.com.


We welcome inquiries for teaching positions at our five locations in Florida and the British Virgin Islands. 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, Rob@OffshoreSailing.com, and Steve Colgate, Steve@OffshoreSailing.com.


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, 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 Vice President of Sales and Technology Deb Marlor, Deb@OffshoreSailing.com.