Offshore Sailing School Is Hiring!

Offshore Sailing School job opportunities are all about being out on the water.  Whether teaching or selling for Offshore, you are providing a quality lifestyle that makes our customers happy! 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 are currently available in Southwest Florida and the British Virgin Islands. If you have excellent “people” skills, teaching experience on keelboats and cruising sail and power yachts, we want to talk to you.

HOUSING AVAILABLE: Minimum 3-month housing may be available at rent below current market levels in Southwest Florida for a US Sailing Certified Instructor at Basic Keelboat or higher level. Act fast, just one apartment is available.

Instructors assigned to 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 have legal authorization to work in the U.S. Those who wish to work in the British Virgin Islands must have a valid BVI issued work permit. If you do not currently have one, we will help you with this process.

Full-time Offshore Sailing School instructors are salaried. Your employment package also includes bonuses, 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.

View more instructor details here. 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 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? We are seeking a full or part time person for our popular sailing school branch 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. 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 email your Application for Employment to Offshore’s CEO/President Doris Colgate with a short paragraph explaining why you would like this job.


From time to time we have full- and part-time sales opportunities, working at Company Headquarters in Fort Myers, FL. This position requires excellent phone and in-person communication skills, attention to detail, and proven ability to close sales. Sailing or boating experience, 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 achieve individual and company sales goals, ability to quickly adapt to reservations software, and ability to 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. No cold-calling involved.

Compensation for full time employees includes base pay and commission; plus paid time off, medical benefits, and free sailing courses. 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, attention: Beth Oliver, VP, Director of Sales & Marketing (pictured above).