Flotilla Skipper

As a Flotilla Skipper, you will be responsible for leading a team and providing exceptional support to our clients. Your strong leadership skills, calm demeanour in challenging situations, and ability to communicate effectively will be essential in ensuring our guests feel confident and secure during their sailing adventures.

• RYA Day Skipper Qualification
• Strong leadership and communication skills
• Ability to remain calm and assertive in challenging situations
• Experience in sailing and knowledge of boat maintenance
• Tidy appearance and professionalism, as you represent the company to clients
• A friendly and approachable demeanour, especially when working with beginners

1. Build Up (Pre-Season - Sailing Holidays is the only flotilla company to offer this vital learning experience!):

Build up is arguably the most important part of the flotilla season! It is an excellent opportunity to learn about our flotilla yachts, ask questions, and gain important skills (especially if there are any gaps in your knowledge) before guests arrive. It's also a great chance to meet the rest of our flotilla team and get to know your crew, who you'll be sharing the lead yacht with throughout the season.

On arrival, skippers move straight onto the lead boat and are quickly assigned their own fleet of 10–11 boats. As a skipper, you will be responsible for the upkeep of the sails and running rigging, the maintenance of on-deck equipment, and assisting our engineering team with underwater work, steering, and rudder systems.

You will have 5/6 weeks to get your fleet ready for the charter season. It can be a steep learning curve but you will be paired and trained by senior shore-based staff.

2. Sailing Season:

The charter season starts at the end of April and continues through until the end of October. During this time you will be living and working as one of a team of three on your Lead Boat.

During the flotilla season tasks will include, but not be limited to:

• Conduct client briefings on the first day of the flotilla, outlining safety protocols and yacht operation
• Each day, you will hold a briefing to walk guests through the plan for the day, including the intended passage, any safety considerations, the expected weather, and clear guidance on mooring procedures and instructions
• Monitor and manage mooring, ensuring safety during storms or high winds
• Provide assistance with client issues related to sails or rigging, both in port and at sea
• Complete scheduled services every fortnight and maintain the condition of client dinghies

There is no hierarchy on the Lead Boat, regardless of position, and the best lead crews work seamlessly together as a team respecting each other’s skills and opinions.

3. Lay-Up (Post-Season):
Lay-up, at the end of the season, normally lasts for one week. During this period all the yachts are prepared for the winter. Skippers are required to:

• Winterise the lead yachts
• Check and record all damage to hull/gel coat/deck
• Note any damage to rigging
• Wash and dry, fold and label all sails, biminis, and sun awnings
• Wash and powder all ropes and store
• Cover all hatches and make the boats watertight

Why choose Sailing Holidays Ltd for my Summer Season?

• A comprehensive training programme
  Benefit from an extensive pre-season build-up that allows you to strengthen existing skills and develop valuable new ones. Sailing Holidays is the only flotilla company to offer a comprehensive programme with excellent training prior to the flotilla season
• Friendly and supportive management
  Our approachable management team is always on hand to offer guidance, encouragement, and practical support throughout the season
• Work as part of a close-knit crew
  You’ll operate within a dedicated team of three – a skipper, engineer, and host – giving you the opportunity to thrive in a collaborative, team-focused environment
• Consistent crew pairing for the season
  From arrival, you are paired with the same lead crew for the entire season. This continuity helps forge strong working relationships, excellent communication, and often lifelong friendships
• Ownership of your own fleet
  Each lead crew is allocated a dedicated fleet of yachts for the duration of the season, with no swapping between flotillas. This provides an in-depth understanding of each vessel and ensures smooth, seamless transitions for guests