New Offshore Sailing School Jobs − We are Growing and Hiring!

New Offshore Sailing School job opportunities take you out on the water, in locations with water views, or in a fun office environment selling fun! See which job fits you best below, then download our Application for Employment; scan and send it to the contact person listed for each position.


Full- and part-time opportunities to teach short sailing lessons or comprehensive certification courses are currently available. Join our faculty team at our six locations in SW Florida and the British Virgin Islands. If you have excellent “people” skills, plus teaching experience on keelboats and cruising sail and power yachts we want to talk to you.

Instructor/sailors who take customers out for rides or sailing lessons must have great people skills and proven sailing experience on boats similar to the Colgate 26 used for these activities. For 2-day to 8-day certification courses, instructors need US Sailing instructor certification at the Basic Keelboat level or higher (or at time of hiring have the skills to pass these levels), 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.

Full-time Offshore Sailing School instructors are salaried, with additional bonuses paid for each course taught. Your employment package also includes paid time off and medical benefits which kick in after a brief probationary period.  There is never a dull moment when working with Offshore, with the possibility of advancement for qualified individuals seeking a career in this rewarding world of sailing and boating education.

If you would like to join our dedicated team, 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,  Please also include a short paragraph in your email, outlining why you would like to work at Offshore.


Want to work with a water view, where boats come and go, and customers are looking for fun things to do? This new position just opened up at our popular sailing school branch located at South Seas Island Resort on Captiva Island, FL. Working in a casual, outdoor environment, you will greet customers, sell and schedule on-water lessons and shore-based activities – working side-by-side with the branch manager, instructors and technical team. Offshore’s on-site office at this location is open 7 days a week with weekend and weekday work schedules covered by full and part-time staff working 40-hour weeks or less. For more information, please download this complete Captiva Customer Service/Sales Rep job description, and email your Application for Employment to Offshore’s CEO/President Doris Colgate with a short paragraph explaining why you would like this job.


Here’s another great sales opportunity – a new opportunity for one full-time sales associate to join our Headquarters sales team in S. Fort Myers, FL. This position requires excellent phone and in-person communication skills, attention to detail, ability to close a sale. Sailing experience and a passion for sailing and boating or a strong desire to learn to sail is important. 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, 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 who like to learn. All leads come from direct response to Offshore Sailing School’s marketing efforts; there is no cold-calling involved.

Compensation for full time employees includes base pay and commission; plus paid time off and medical benefits.  In addition, you get to take sailing and boating courses at no charge, and enjoy sailing on company boats with staff from time to time (if you are so inclined) . 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 Beth Oliver, VP and Director of Sales & Marketing (pictured above).