PROFESSIONAL & Volunteer CREW OPPORTUNITIES
Sailing Ships Maine operates seasonal sail training programs on the coast of Maine. Crew are hired to work aboard our vessels Schooner Sara Jane and Sloop Brightside teaching our 5-day overnight accredited programs (Monday morning through Friday afternoon) and preparing our boats for the season.
Sailing Ships Maine is committed to providing teens an experiential learning opportunity onboard a sailing ship to expand leadership skills, discover the ocean environment, and learn all aspects of sail training that may lead them to consider further maritime training.
We seek volunteers and professional crew who are excited to teach and engage the minds of middle and high school aged students during their intense weeks together.
In addition to the positions listed below, we offer internships and apprenticeships to support our educational mission.
Contact Sailing Ships Maine at info@sailingshipsmaine.org.
Captain – Educator
Seasonal Position April 2026 - October 2026
Category: Deck: Licensed
Seasonality: Seasonal
Location: Freeport, Maine, United States View on Google Maps
Start Date: April 1, 2026
End Date: October 31, 2026
Application Deadline: December 31, 2025
Job Description:
Want to sail in coastal Maine, lead intentional experiential education opportunities, and mentor youth?
Sailing Ships Maine is seeking a second captain/educator for the 2026 season.
Our mission is to give youth meaningful experiences on the water, offering them opportunities for self-discovery, leadership development, community building, and skill building — all rooted in a maritime sail training foundation. Our fleet is made up of small passenger sailing vessels, ranging from 36-60 feet, each crewed by a captain and mate with up to six students. Our trips — which primarily run in Casco Bay, Maine — generally run between five and seven days in length.
The second captain operates under the direction and leadership of the lead captain.
Program & Itinerary:
At Sailing Ships Maine, we are passionate about youth education and providing hands-on outdoor opportunities for students of all backgrounds. Not only will youth learn about sailing, teamwork, and living on the water, they will learn something about themselves. The programs we provide offer youth the chance to be present in nature and take ownership over their own experience. Our programs are phone/technology free, non-judgmental, safe and fun spaces for youth to grow. We are seeking a captain who is passionate about offering thoughtful experiential education.
Responsibilities:
Vessel Command: Ensure safe navigation and operation while adhering to all U.S. Coast Guard regulations.
Educational Leadership: Instruct participants in maritime skills, including sailing techniques, weather observations, navigation, safety protocols, and marlinspike seamanship. There are also opportunities to teach environmental education lessons.
Mentorship: Guide students and crew while modeling strong leadership skills, excellent listening ability, compassion, open-mindedness, and community building.
Maintenance: Supervise and perform routine maintenance and necessary repairs to ensure the vessel’s optimal condition. Documentation of all maintenance accomplished.
Safety Management: Follow safety procedures to protect crew and students while underway.
Qualifications/Experience:
* Valid USCG captain’s license
* Strong instructional and interpersonal skills, with a passion for teaching and mentoring
* Experience teaching middle/high school aged youth
* Excellent risk assessment, planning, and communication skills
* Adaptable, self-motivated, strong teamwork ethic
* Commercial sailing experience preferred
* Traditional sail training experience preferred
* Experience on traditionally rigged vessels preferred
* Proficiency in vessel maintenance, ideally including mechanical and electrical systems
* Ability to pass a pre-employment drug test & background check
Compensation: $4,000 to $4,999 Monthly
Benefits:
* Pay based on experience, licensure and position
* Need-based travel and/or housing stipend
* Assistance advancing USCG licensure/certifications
* Opportunity to build program-development skills
Required Certifications
Medical: CPR
Apply
Have the following ready to upload in pdf, png, or jpg format:
Resume
References
Cover Letter
Send your application to captain@sailingshipsmaine.org.
Category: Deck: Unlicensed
Seasonality: Seasonal
Location: Freeport, Maine, United States View on Google Maps
Start Date: April 1, 2026
End Date: October 31, 2026
Application Deadline: December 31, 2025
Job Description:
Want to sail in coastal Maine, lead intentional experiential education opportunities, and mentor youth?
Sailing Ships Maine is seeking deckhand educators and/or mates for the 2026 season.
Our mission is to give youth meaningful experiences on the water, offering them opportunities for self-discovery, leadership development, community building, and skill building — all rooted in a maritime sail training foundation. Our fleet is made up of small passenger sailing vessels, ranging from 36-60 feet, each crewed by a captain and mate with up to six students. Our trips — which primarily run in Casco Bay, Maine — generally run between five and seven days in length.
Program & Itinerary:
At Sailing Ships Maine, we are passionate about youth education and providing hands-on outdoor opportunities for students of all backgrounds. Not only will youth learn about sailing, teamwork, and living on the water, they will learn something about themselves. The programs we provide offer youth the chance to be present in nature and take ownership over their own experience. Our programs are phone/technology free, non-judgmental, safe and fun spaces for youth to grow. We are seeking crew who are passionate about offering thoughtful experiential education.
Responsibilities:
* Co-leading multi-day overnight youth programs, teaching both nautical skills and environmental education lessons
* Work closely with captain to develop and execute lesson plans for middle school and high school students
* Opportunity to develop individual lessons based on personal skillset/interests
* Participate in pre- and post-season maintenance periods, as well as ongoing shipboard maintenance during the season
Qualifications/Experience:
* A strong passion for working with youth in dynamic outdoor environments
* Experience teaching middle/high school aged youth
* Strong interest in sailing overnight with middle/high school students
* Excellent communication skills
* Adaptable, self-motivated, strong teamwork ethic
* At least 60 USCG documented sea days
* Ability to pass a pre-employment drug test & background check
Compensation: $1,600 to $2,500 Monthly
Benefits:
* Pay based on experience, licensure and position
* Need-based travel and/or housing stipend
* Assistance advancing USCG licensure/certifications
Required Certifications
Medical: CPR
Apply
Have the following ready to upload in pdf, png, or jpg format:
Resume
References
Cover Letter
Send your application to captain@sailingshipsmaine.org.
Head of School
One Year Americorps Stipended Position starting spring 2026
Sailing Ships Maine, a 10 year old non-profit, creates life-enhancing opportunities for teens of all abilities and income levels to experience life on the ocean. We operate several sail training vessels on the Maine coast and we send our students to sea on vessels operated by others who share our commitment to youth education at sea.
We seek an experienced educator, possibly retired, to create a brand new community college level program to recruit and train the next generation of sail training captains and mates. This is a full-time, one-year position to lead the effort to launch the new workforce development program.
The new program will recruit and train 12 passionate educators to become licensed captains. This will be a two year tuition-free program with the goal of helping students earn their entry level USCG Captain’s licenses and getting subsequent job placements in the sail training industry.
The ‘Head of School’ will be the person who develops the plan, manages the funding, recruits the first two classes of students and starts the program. The successful Head will then either continue for a second year or recruit their successor.
Benefits:
This is a federally stipended Americorps VISTA program position.
Pay: $27,000 for 1700 hours in 12 months
Housing and Travel stipend
Based in Portland, Maine; remote work by agreement
The goal of the program is to recruit and train captains and deckhands who can provide sail training opportunities for the future.
Graduates of this new school would have opportunities with many educational and sailing organizations.
If you are interested or know the right candidate, please reach out to info@sailingshipsmaine.org or click here to schedule a phone call.
About Sailing Ships Maine:
We take middle and high school students to sea for 5 day (4 night) accredited programs taught by two crew, a USCG licensed captain and a deckhand-educator. Our accredited program in Nautical Science includes navigation, safety, engineering, seamanship and is an immersive learning experience for students. Students are required to learn to operate the vessel, keep it clean, follow crew’s guidance, cook meals themselves (with supervision) and work hard all week. Crew work hard to make this happen and everyone goes home proud but tired. Crew have most weekends off though there are some weeks where the program starts on a Sunday afternoon and ends on a Saturday morning – but that is the exception. Crew sail the overnight program 3 out of 4 weeks. The 4th week is either maintenance or teaching in our middle school daysail programs on 23’ Pearson Ensign sailboats. Crew will sail an average of 20 days per month during the sailing season (June through September).
Our vessels:
Schooner Sara Jane, a 42 foot wooden Murray Peterson Coaster III
Brightside, a 36 foot Palmer Johnson sloop
Four Pearson Ensigns
One 32’ fixed-seat rowing gig
Misc. dinghies and support boats
Job Requirements for our Captains:
A current USCG license
Experience teaching high school students
Experience managing sailing vessels including both operation and maintenance
Ability to manage people, both deckhands and other captains
Interest in sailing overnight with students
Vessel maintenance experience
Teaching experience
Shoreside organizational development experience
Excellent communication skills