PRIVATE | Experienced Skipper | Oyster 595

This is a remote position. Experienced Captain | Oyster 595 STARTING OCTOBER we are looking for an enthusiastic teaching Captain to help an active sailing family settle into life with their new Oyster yacht and make the most of the adventures ahead. The plans are still developing but the owners are ready to seize the moment!

The owners are an enthusiastic and adventurous family and al though they have 15 years of coastal sailing experience, they are relatively new to offshore passagemaking and have not yet undertaken serious bluewater cruising. They are keen to learn, develop their skills, and gain confidence under the guidance of an experienced skipper.

From September to October 2026, the programme will focus on vessel handover, familiarisation, owner training, and preparations for the Atlantic crossing. In November, the yacht will take part in the ARC Atlantic Rally. The winter and spring of 2027 will be spent cruising the Caribbean and exploring the Leeward Islands for two to three months, before plans turn to summer 2027, when the yacht may either return to Europe via Greenland and Iceland or continue westward for further adventures.

Requirements

Yachtmaster Offshore/Ocean (or equivalent) preferred. Practical engineering skills, including diesel engines and onboard systems. Offshore and ocean passage making experience. Strong sailing yacht maintenance knowledge. Ability to troubleshoot and manage technical issues. Experience preparing yachts for extended cruising.

Confident teaching and mentoring owners and crew. Organised, professional and safety-focused. Oyster or similar bluewater cruising yacht experience is advantageous. Most importantly, we're looking for someone who is personable, patient and enjoys helping owners develop their skills and confidence while sharing in an exciting cruising programme.