Employment Opportunities

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.

Florida & The British Virgin Islands


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.

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. Please download the application, scan and send it with your sailing resume to Randon@OffshoreSailing.com. Please also include a short paragraph in your email, outlining why you would like to work at Offshore.

Ft. Myers, FL

Sales Associates

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. Compensation package includes base pay and commission. Please download the application for employment, scan and send it to HR & Finance Specialist, Cheryl Jones, SHRM-CP (Cheryl@OffshoreSailing.com) with your resume and a short paragraph stating why you would like to work for Offshore Sailing School.

Compensation for full time employees at Offshore Sailing School includes paid time off, medical benefits, and free sailing courses.