Offshore Sailing School Job Opportunities

Want to work for a fun lifestyle company? Offshore Sailing School career opportunities are all about loving and living the sailing and boating lifestyle. See which job fits you best below, then download the Offshore Sailing School APPLICATION FOR EMPLOYMENT; scan and send it to the contact person listed for each position.


Full-time salaried and seasonal (minimum 4 months) opportunities are currently available in Florida and the British Virgin Islands. If you have excellent “people” skills, strong teaching, sailing and boating experience on keelboats and cruising sail and power yachts, we want to talk to you.Oportunidades de Empleo

Offshore instructors teach beginners and experienced sailors and boaters on Colgate 26 keelboats and 40′ to 50′ sailing yachts (monohulls, catamarans) and power-cats. All courses are taught to US Sailing certification standards. Instructors are expected to hold US Sailing instructor certification at the Basic Keelboat level or higher (or at time of hiring have the skills to pass these levels), plus a USCG license or have the experience to obtain one. Candidates who wish to work in the United States must be U.S. citizens or have legal authorization to work in the U.S. If applying for an instructor position in the British Virgin Islands you 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 with an employment package that includes bonuses, paid time off and medical benefits.


With a growing fleet of company-owned monohulls and catamarans, Offshore Sailing School is seeking a skilled technician who can move between Florida locations to keep the company’s fleet of 26′ to 45′ sailboats in A-1 condition. This position comes with responsibility and variety, reporting to the Director of Operations and US Regional Manager. If you would like to join our dedicated team as an instructor, base manager, or fleet technician, 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.


From time to time we have full- and part-time sales opportunities, working at Company HeadquartersOportunidades de Empleo 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.


Offshore Sailing School is seeking a specialist in web, social media marketing, video production, and IT applications with strong experience in all areas of digital marketing. This position includes working with the Operations Team on creating online classroom content, managing and editing the company’s websites, and collaborating on presentations and opportunities that create income for the company through digital applications.

Compensation for full time sales associates, marketing assistant and administrative employees includes base pay and commission; plus paid time off, medical benefits, and free sailing courses. Please download and fill out the 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 the job you are interested in to Beth Oliver, VP Director of Sales & Marketing at (pictured).