A Brief Overview

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. We offer 8 different programs that are either 14, 18, or 21 days from the first week of June until the last week of August.  Fleet sizes range between 2-6 boats (about 30-80 students and staff) that sail amongst the British Virgin and Leeward Islands in the eastern Caribbean. The majority of our students are aged between 11 and 19. We also have a program for college students.

The sailing staff live aboard the monohulls and catamarans 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 they 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 group setting on their home boat as well as a large group setting when we have fleet wide events. Students become a family with their crew but have the opportunity to branch out and meet other teens from all over the US and the world.

Our staff teach sailing lessons onboard the boats, lead boat meetings and group discussions, teach water skiing and wake boarding, lead hikes and snorkels, oversee the cooking, lead dance contests—all aspects of the program. We are always on the go. Captains and Mates are led by the Program Director and the Fleet Captain to ensure that standards are being met, everything is running smoothly, and we are accomplishing our goals.

Operations Staff and the Office Manager live on land at our base at Hodges Creek Marina in Tortola and work closely with each of our program fleets and with our dive company, Sail Caribbean Divers. The Office Manager (OM) is the liaison between the NY Office and the Caribbean. The OM coordinates the communication between the fleets, arrival and departure days, as well as setting up fleet events. Operations staff handle equipment maintenance and repair, program inventory and delivery to fleets, transportation for student arrival/departure days, and operation of ski boats for watersport activities.


Typical Staff

The average age of our summer staff members is 26. All staff must have completed two years of college. Staff are chosen for their extensive and varied backgrounds in experiential education and work with teens.

"My daughter thought the staff was excellent and well-trained. They provided strong leadership, were calm, confident, organized and experienced. She said her boat captain was perfect for the job. He listened and cared."
-Ruth Robinson

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 adventure trips for service related experiences or for marine biology research projects. 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 US Sailing or ASA Basic Keelboat Instructors, Scuba Diving Professionals, and persons with Marine Biology backgrounds.

Meet some of our summer sailing instructors:

Hannah Korus Kyle Pierson Sarah Morgan Lee Daniel Klein Kieran Sullivan
Hannah Korus Kyle Pierson Sarah Morgan Lee Daniel Klein Kieran Sullivan


Short bios about our leadership team are also available here.


Benefits of Joining the Sail Caribbean Team

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

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

Support and Feedback - 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 are 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.

Professional Growth - 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.

A Well-Rounded Experience - 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.

Make A Positive Impact! - 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.


Use the menu on the left to learn more about employment Opportunities and How to Apply.

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