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The Island Trust – Fleet Skipper

Skipper across our fleet

A GREAT OPPORTUNITY to further your professional sailing career with one of the foremost youth sail training providers in the UK.  We are seeking a sailing professional to join our team of sea and land-based staff – a Skipper to work across all three vessels of our sail training fleet.

The Island Trust provides life-enhancing, residential and day-sailing activities for young people with special needs, disabilities, and those experiencing hardship and deprivation. We award disadvantaged young people the opportunity to not only widen their horizons but also develop their skills and capabilities through the joy and challenge of learning to sail.

Voyages range from youth residential sail training weeks for groups and individuals and day sailing for profoundly disabled young people, to a small number of commercial adult RYA courses and voyages.

Visit our website for more information and how to apply:

The position is full-time  – ending mid November 2022 with the possibility of extending.


During the sailing season, you will

  • Principally be required to Skipper and sail any vessel owned, managed or chartered by the Trust.
  • Skipper school and youth group charters as well as charters for teenagers and adults.
  • Undertake charters that will vary in duration and destination.
  • Assume authority at all times, and make decisions with regard to the safety of the vessel.
  • Ensure compliance with the MCA codes of practise.
  • Maintain and train staff in the use of all on board safety equipment.
  • Ensure the safe navigation of the vessel.
  • Maintain a watch consistent with the requirements of good seamanship.
  • Prepare for the arrival of the charterers.
  • Work with the charterers collectively or individually in pursuit of their objectives, including attending to the needs of customers whilst on board.
  • Work in accordance with our Safety Management System.
  • Be responsible for uploading any DofE Gold Residential and DofE Expedition assessments to the DofE portal at the end of each voyage.
  • Promote the work of the Trust through:
  • Taking participant promotional photographs and video during a voyage;
  • Shared responsibility for social media posts with co-workers.

During the non-sailing season, you will

  • Be engaged in whatever routine maintenance tasks the Operations Manager deems necessary for the continued safe use and long-term benefit of the vessels;
  • Be available to assist in clerical, administrative or marketing tasks as agreed with the Operations Manager.
  • Share responsibility for social media posts with co-workers.


£24,000 pa (minimum).


The vessels will generally be moored at Plymouth Yacht Haven for south coast and Channel voyages. You may need to join the vessel elsewhere in the UK throughout the season.


Moosk, 1906 gaff yawl, 58ft, 8 guest berths

Pegasus, 2008 gaff-rigged pilot cutter, 72ft, 10 guest berths

Johanna Lucretia, 1945 Topsail Schooner, 96ft, 12 guest berths

Skills and attributes:

  • Qualified to Yachtmaster Offshore level (commercially endorsed)
  • In-date medical qualification e.g. ENG1 or ML5 (essential if not included in above)
  • Cruising instructor (sail) preferred
  • Prepared to undertake DBS check and further training as required (essential)
  • Experience in refitting traditional vessels (preferred but not essential)
  • Experience of working with young people (preferred but not essential)
  • Able to understand the (sometimes complex) needs of others and moderate working practices and approaches accordingly
  • Empathic and compassionate
  • A good team player and excellent communicator

To apply:

Please email a covering letter and CV to [email protected]

If you would like to discuss the post in more detail, please contact Tom Walker, Operations Manager on 07785572680.

Closing date for applications: 11 April 2022

Employment is with The Island Trust’s trading subsidiary Island (Cutter) Ltd.
All voyages are operated by Island (Cutter) Ltd.

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