Volunteer as Captain or Crew

A Sailing Reprieve For Those Affected by Cancer and All Who Love
Them

We are always looking for compassionate, experienced people who embody the skill and the personality to have the great honor of serving and hosting our guests aboard S/V Gypsy Wind. Below, find the descriptions, requirements, and form for signing up. There are three levels of crew: Captain, Crew 1, and Crew 2.

Please note, Healing Winds Vermont does not teach sailing classes. We are in need of volunteers that are knowledgeable about sailing.

CAPTAIN – The Captain of the sloop Gypsy Wind, is responsible for the safety and well-being of both the crew and passengers, and the safe and efficient operation and management of the vessel.

The Captains’s responsibilities on S/V Gypsy Wind include but are not limited to:
– SAFE OPERATION OF THE VESSEL.
– Decision-making in all aspects of operation from cancellation and postponement of programed sails.
– Training crew in all aspects of vessel operations including the safety, program, public relations and community.
– Managing the crew in such a way as to create a strong, cohesive team.
– Working to maintain positive relationships among S/V Gypsy Wind dock master and other vessels.
– Prompt written and verbal incident reports to the Executive Director.
– Vessel maintenance.
– Maintaining clear communication with the Education Director, to ensure the best quality respite program.

Qualifications: (*Not required- please contact us)
– Ideally, a current USCG license (aux. sail)
– An understanding of the Healing Winds Vermont organization, mission, and structure.
– Experience as the Captain of Gypsy Wind or a sailing vessel of similar size.


CREW 1 – The Crew 1 (First Mate) of the sloop Gypsy Wind, is responsible for the safety and well-being of both the other crew and passengers, and the safe and efficient operation and management of the vessel.

The Crew 1 (First Mate’s) responsibilities  on S/V Gypsy Wind include but are not limited to:
– Ensuring compliance with all federal, state and local safety regulations with special regard to the US Coast Guard
– Managing the vessel and passengers while sailing
– Maintaining a close relationship with the Lead Captain and Captain of the sail.
– Maintaining a close relationship with Execute Director of Healing Winds Vermont
– Work to maintain a positive relationship between the boat, passengers, Captain and City of Burlington waterfront
– SAFE OPERATION OF THE VESSEL
– Preparing to get under way & docking
– Understanding various wind conditions
– Start engine
– Conduct man overboard procedures
– Raise and take down sails
– Read charts, compass, nautical equipment
– Know the ‘rules of the road’ – who has right of way
– Know what various navigation aids mean
– Attend to the skipper
– Respecting and following out the decision-making of the Captain in all aspects of operations
– Complete training in all aspects of vessel operations including the safety, program, public relations and community
– Work together to create a strong, cohesive team
– Help with vessel maintenance

The Crew 1’s skill level requirements on S/V Gypsy Wind include but are not limited to:
– COMPETENT, Confident Sailor with prior sailing experience on board vessels of 25’ or longer in length.

Qualifications: (*Not required- please contact us)
– Ideally, a current USCG license (aux. sail)
– An understanding of the Healing Winds Vermont organization, mission, and structure
– Experience as the Captain of Gypsy Wind or a sailing vessel of similar size


CREW 2 – (Ambassador) of the sloop Gypsy Wind, is responsible for the safety and well-being of both the other crew and passengers, and the safe and efficient operation and management of the vessel. 

The Crew 2 (Ambassador’s) responsibilities on S/V Gypsy Wind include but are not limited to:
– Ensuring compliance with all federal, state and local safety regulations with special regard to the US Coast Guard
– Maintaining a close relationship with the Crew #1 (First Mate), Lead Captain and Captain of the sail
– Work to maintain a positive relationship between the boat, passengers, Captain and City of Burlington waterfront
– SAFE OPERATION OF THE VESSEL
– Basic knowledge of line-handling, safety
– Liaison between passengers, assisting guests with water, food, and general aide
– Taking photos of the group
– Talking and making sure that their experience is stellar and comfortable
– Preparing to get under way & docking
– Conduct man overboard procedures
– Help raise and take down sails
– Attend to the skipper
– Respecting and following the decision-making of the Captain in all aspects of operation
– Complete training in all aspects of vessel operations including the safety, program, public relations and community
– Work together to create a strong, cohesive team
– Help with vessel maintenance
– Maintaining clear communication with the Captain, Lead Captain and Executive Director, to ensure the best quality
respite program

The Crew 2’s skill level requirements on S/V Gypsy Wind include but are not limited to:
– Ability to take direction
– Ability to learn on the job
– Positive Attitude
– Good work ethic and teamwork
– Professional appearance
– Ideally sailing experience on board vessels of 25’ or longer in length

Qualifications: (*Not required- please contact us)
– Ability to be compassionate
– An understanding of the Healing Winds Vermont organization, mission, and structure
– Experience working with people in customer service
– Boat / yachting experience – not a beginner sailor