Offshore Sailing School Employment Opportunities

View all current available openings at Offshore Sailing School, including sailing instructor jobs, sales positions and more below. You may download our Application for Employment here. When completed, please send to the contact person listed for each position.


This career position is based at our premier Florida location on Captiva Island. Key responsibilities include: Evaluate, train, schedule and supervise staff of full time and part time instructors; train, schedule, supervise and hold responsible cleaning and maintenance personnel; insure the entire Captiva Island fleet is maintained in A-1 cosmetic and mechanical condition (currently Jeanneau 439; , 10 Colgate 26 keelboats, chase boat and ribs); prepare and submit any required reports on daily, weekly and bi-weekly basis, including payroll detail; maintain cosmetic and physical appearance and functionality of classrooms, office, storage areas and docks.
We want to talk to you if you have the following: Strong management experience; expert sailing skills and knowledge relevant to the courses we teach and boats we teach on; boat maintenance aptitude; expertise in coaching or teaching sailing, with willingness to attain US Sailing instructor certification at the highest levels if not already in hand; proficiency in Microsoft Office operating systems, CRM and reservations systems.
This position reports to the Chief Operations Manager, and is expected to communicate with all other branch managers to share best practices and work closely with headquarters sales and marketing team to ensure branch revenue growth.Please fill out our employment application, send it with your work and sailing resume, and a cover letter highlighting why you are the right person for this position to Bryce Jackson, Bryce@OffshoreSailing.com.


We have openings for experienced full time sales associates, to join our sales team at Offshore’s busy Ft. Myers, Florida headquarters. This position requires excellent phone sales skills, sailing experience and a passion for sailing and boating or a strong desire to learn to sail. The right candidate will have a proven track record selling vacation packages and experiential learning products, 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. Please download and fill out the Offshore Sailing School Application for Employment, scan and send it with your resume and cover letter highlighting the three most important reasons why you are the right person for an Offshore Sailing School sales position. Send all correspondence to Wendy Bishop, Sales Manager, Wendy.Bishop@OffshoreSailing.com.



Our courses are in such high demand, we are actively interviewing for qualified instructors to fill open positions at our six locations – four in Florida and two in the British Virgin Islands. Considered the best sailing jobs in the industry, Offshore Sailing School instructors are known for their excellent sailing knowledge and experience, and the ability to communicate that knowledge to clients with humility and patience. If you have excellent “people” skills, plus teaching experience on keelboats and cruising sail and power yachts we would like to talk to you. 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. If you do not currently have one, we will help you with this process. It takes several months to apply for and get the permit. Please download and fill out the Offshore Sailing School Application for Employment, scan  and send it with your sailing resume to Bryce Jackson, Chief Operations Manager, Bryce@OffshoreSailing.com.