A group of Sail Caribbean staff members posing for a photo on a sailboat.
A group of Sail Caribbean staff members posing for a photo on a sailboat.
Working driving a small dingy boat.


At Sail Caribbean, our mission is to inspire self-confidence, foster personal growth, and instill leadership skills through the highest quality Caribbean adventures. Our programs and staff empower students to work as a team to take on the responsibilities of life on board a large sailboat. Our 10 different program categories are tailored to suit different areas of interest and age groups.

Three workers posing together on the beach.
Group photo of some workers in the water.

Life Aboard Your Yacht

We pride ourselves on taking great care to hire the best and most dynamic team of staff members possible. The sailing staff members live aboard the monohull and catamaran yachts with the students—much like cabins in a traditional sleep-away camp. Captains always sail on the same boat with the same crew. Mates have a home boat but regularly rotate within the fleet so that students can connect with more staff members and vice versa. This allows us to have an extremely tight-knit group of instructors and students, providing a remarkable support system for everyone involved. Our students and staff benefit from both a small “family”-style setting on their home boat as well as a larger group setting when we have fleet-wide events. Students become a team and community with their fellow crew, Captain, and mate, but still have the opportunity to branch out and meet other teens and staff from all over the US and the world.


Our staff is composed of an incredible network of professional men and women from all over the world. Many of our alumni staff is still involved in aspects of our operation even though they aren’t in the Caribbean with the students anymore.

Just like our students, our staff responds to new challenges, experience personal growth, learn from another, and become deeply connected through their commitment to the students, the program, and each other.

During each program, there are frequent “check-ins” and daily staff meetings to help staff members perform at their highest level. In order to ensure that staff is receiving the support they need; we place a strong emphasis on feedback and daily collaboration. Our cooperative efforts encourage an environment that is open and focused on our achievements.

Each summer that a staff member returns the potential for moving up the ranks greatly increases. Pay also increases each summer you return and with each new leadership role that you take on.

Our staff get to travel within the beautiful Eastern Caribbean, become friends with a remarkable group of people, refine their big boat sailing skills and gain tangible experience in marine science, conservation, and outdoor adventure education.

It is incredibly rewarding to see your crew dock their boat, conquer their fear of scuba diving, discover a passion for service learning or break out of their shy exterior. It’s an amazing feeling to know that you have positively impacted a teenager’s life.

We accept applications from November through April