Skip to main content.


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 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. 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. Most of our staff will live and teach onboard one of our student boats.


Join a global network of professionals who remain connected and involved beyond their time in the Caribbean. Our staff, a blend of men and women from around the world, form a hard-working family that supports each other and our mission.

Embrace challenges and experience significant personal development. Like our students, our staff learns, grows, and connects deeply through dedication to our students, the program, and mutual support.

Benefit from regular check-ins and daily meetings designed to enhance performance. We emphasize feedback and collaboration, fostering an open, achievement-focused environment.

Return each summer to increase your chances of career advancement and higher pay. New leadership roles offer opportunities for professional growth in a dynamic setting.

Travel the stunning Caribbean, forge lasting friendships, hone your sailing skills, and gain valuable experience in outdoor education, marine science, and conservation.

Experience the profound satisfaction of influencing young lives. Whether it’s helping students dock a boat, overcome a fear of scuba diving, or discover new passions, your role is key in shaping their future.

We accept applications from November through April