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Staff Expectations

Group of staff smiling together for a photo.
Group of staff smiling together for a photo.
Staff member giving underwater scuba instruction.


Although much has changed since our beginning in 1979, the same values on which Sail Caribbean was founded continue to drive all of our programs today: respect for one another and the sea; belief in the great things young people can achieve; and simply doing things right. Our staff’s commitment to these ideals is reflected in our mission statement: to inspire self-confidence, foster personal growth, and instill leadership skills through the highest quality Caribbean adventures.

Sail boat in the ocean.
Staff members driving a boat.

We are committed

Our staff members are committed to our philosophy and our students through both the fun times and the challenging times. Yes, you are in the beautiful Caribbean, but you are not on vacation—it is a ’round-the-clock’ job and we hold our staff to a very high standard. There is time off, but it might only be two days the entire summer. The students always come first.

Our Expectations

It is a great source of pride that our staff members are consistently evaluated by students and parents as being responsible, knowledgeable, considerate, and fun. We seek individuals to join our team who can maintain this balance and approach their job with both professionalism and enthusiasm.

As staff members, it is our responsibility to create and maintain a safe and comfortable environment for our students. Our staff is expected to set a positive example and never turn a blind eye to actions that might spoil the experience for others, or put anyone at risk. As safety is our #1 priority, it should go without saying that we have a strict, absolute zero tolerance policy for staff using drugs while employed by us, and alcohol is not permitted while on program. The Sail Caribbean ‘rules’ are clearly laid out to the students and staff. At Sail Caribbean, students are automatically sent home for smoking, drinking, or using drugs. Students, parents, and staff appreciate that our rules are fair, well understood, and enforced without exception. Please know that part of the application process is an official background check done by an independent agency.

We rely on every staff member to be accountable for the responsibilities associated with their job description. Each individual is essential to the overall success of our programs. Time management, attention to detail, and clear communication are expected from every staff member.

The average age of our summer staff members is 23. All staff must have completed two years of college. Staff members are chosen for their extensive and varied backgrounds in experiential education and work with teens. Many of our sailing staff are distinguished dinghy sailors, big boat racers, or grew up cruising in all parts of the globe. Others have vast experience leading educational, service-related or adventure travel trips for teens. Many others are marine or environmental science majors, teachers, or researchers. On the land or on the water, our staff have worked with teens as teachers in the classroom, coaches on the field, guides in the backcountry, instructors at yacht clubs, and counselors at camps.

Sail Caribbean staff members are energetic, highly motivated, have a team-oriented mindset, and serve as great role models for our students. We are excited about igniting a passion for learning in our students. In addition to these qualities, we are always looking for IYT, RYA, US Sailing, or ASA Instructors, Scuba Diving Professionals, and persons with Marine Biology backgrounds.

We accept applications from November through April