Flotilla Skipper



Reports to

Yacht Manager


April - October

Job Summary

You will have a passion for sailing and have the ability to live and work in a small team. You will be self-motivated and able to work without supervision. You will be required to be creative, supportive, hardworking and confident in your own work methods. Working under the Yacht Manager in this hands-on role, you will be responsible for the day to day running of a fleet of yachts, ensuring all standards are maintained to the highest level. Your main day to day tasks will include: guest briefings, passage planning, obtaining weather forecasts, housekeeping duties, guest relations, safety checks, sailing and mooring support, preventative maintenance, reactionary maintenance and also evening social activities. Each flotilla can host up to 50 guests. 

With the support and guidance of your Manager you will take full ownership for ensuring all sailing activities are delivered in accordance with both Trek and IYT guidelines. During your first week of work you will have the opportunity to work closely with more experienced staff until you are confident working on your own. Excellent customer service skills and a friendly approachable style are essential in ensuring we provide a safe and enjoyable experience for all our guests. You’ll always be ready to deal with any problems that arise, albeit at sea or on the quay.

In addition to the Yacht Manager you will also be supported by the shorebased Engineer. You and the Flotilla Mate are the only 2 crew living and working onboard the lead boat. All other in-resort staff and management support are shorebased and ready to assist as and when required. The Flotilla Mate will be a confident sailor with excellent customer service skills and a passion to learn. They will hold their RYA Coastal Skipper, as a minimum. A key part of your role will be to support and develop your Mates sailing skills.  You will create a weekly H&S task list for you and the mate to fulfil. You will gradually train them to fulfil your Skipper duties, in the event of your absence. You will continually pay attention to their general welfare and job satisfaction. Ensuring that all issues that may be raised by them are met with a kind and fair response. All issues will also be passed on to the Manager. 

Flotilla working hours vary from day to day, based on weather forecasts, guest needs, boat issues and journey plans. A typical day will include a Mate and Skipper planning chat at 09:00, followed by a Guest Briefing at 10:00. Finish times will vary. Typically on days with no evening activities you may finish around 19:30, but please note you do not finish work until the last guest boat has moored for the evening. Approximately 3 evenings a week you will be expected to socialise with guests for a meal or drinks.  Work is carried out 6 days a week. Working hours are flexible to the needs of the company. It is really important that all our staff recognise the need to be flexible in their approach to work. The very nature of our jobs means that no two days are the same. Your daily plans will need to be flexible to the needs of your guests and the weather conditions. At times, you may be required to take on extra duties. The role of Flotilla Skipper is a very enjoyable and rewarding role, but it does carry a large level of responsibility with it. You are looking after the safety and wellbeing of guests and boats, away from the immediate support of the manager. It is therefore only suitable for  a mature, level headed and conscientious individual who is committed to delivering the product to the highest standard. A commitment to supporting their own crew.

We pride ourselves on offering our staff a different experience. We do all we can to ensure that your time with us is rewarding and enjoyable. We aim for all of our staff to finish their time with us having gained new qualifications and/or experiences to help further their career. We value all of our hard working staff and love seeing teams building new friendships and enjoying their work year after year. If you want to learn new skills, make lifelong friends, experience a different way of life and immerse yourself in a small Greek community, this is the job for you.

You’ll be able to confidently interact well, and easily build rapport with guests, and other team members alike. If you are an experienced flotilla skipper, that’s great! If you are newly qualified, no problem. We will provide any additional training required to run the flotilla. As long as you are confident, outgoing and have a passion for making people’s holidays.

Key Responsibilities and Tasks

(this list is not exhaustive)

  • Work closely with the Yacht Manager to plan routes and establish daily routines.  
  • Be responsible for daily weather checks and daily passage planning, including back up plans and last minute changes, if required. 
  • Communicate regularly with the Yacht Manager and ensure you are keeping them informed of all your plans.
  • Weekly maintenance checks.
  • Understand the Operating Procedures and ensure they are adhered to at all times.
  • Understand Emergency Action plans and know how to contact key support resources i.e. Port Police, Fire, Ambulance, Management.
  • Along with the Mate, you will give daily briefings regarding the route and daily itinerary.
  • Assist clients with departing and berthing in ports and lunch time anchorages (if required). To ensure optimum welfare for guests and boats.
  • Deal with guest enquiries promptly and conscientiously.
  • Provide informal tuition to guests who lack experience and confidence. Often as part of a 2 day “brush up” course at the start of their holiday.
  • Organise, oversee and assist with changeover days: yacht cleaning, laundry, welcome packs and preparation for arrival of clients.  
  • Ensure client transfers to/from airports/bases run smoothly. 
  • Welcome guests on to their yachts and provide boat and safety briefings upon arrival.
  • Help with any ongoing maintenance of all flotilla yachts whilst away from base, including: marine systems, engines, electrics, plumbing, sails and rigging.
  • Working closely with local suppliers for the provision of services.
  • Responsible for day to day petty cash accounting. 
  • Be available 24/7 for emergency support and assistance for guests and boats. 
  • Deal with first aid needs.
  • Skipper the lead boat.
  • Skipper guests boats if circumstances require it.
  • Ensure you are aware of passage plans and guest locations.
  • Upsell local revenue sources, as and when applicable.
  • Provide ongoing training for the Mate and other staff interested in Yacht skills.
  • Lead boat housekeeping duties (shared with the Mate).
  • Socialising with guests, particularly in the evenings.

Job Requirements

  • RYA Yacht Master (commercially endorsed)
  • RYA Powerboat Level 2 
  • RYA Powerboat ICC (desirable) An ICC is available from the RYA if you have your level 2
  • VHF License (desirable)
  • Valid First Aid certificate
  • Flotilla experience either as staff or a guest
  • Yacht teaching experience 
  • Engine and rigging maintenance experience
  • Confident problem solver, capable of applying logic and initiative to decision making
  • Able to work under pressure and communicate effectively in challenging situations
  • Confident, with training and supporting other team members
  • Experience living and working on yachts (desirable)
  • Experience of living with non-family members and maintaining amicable relationships
  • Excellent customer service experience
  • Highly confident and skilled in safety and on the water rescue techniques
  • Competent Swimmer
  • Clean DBS check
  • Over 20 years of age 
  • Clean and tidy appearance

Basic Package

  • Competitive Salary: With 2nd year increase for returning staff.
  • Flights: To and from Greece at the start and end of your contract.
  • Transfers in Greece: Between the airport and your accommodation at the start and end of your contract.
  • Accommodation: Sharing the lead boat with Skipper –  each with your own cabin. 
  • Insurance: Whilst working you are covered under our Public Liability and Professional Indemnity policies. In addition, you will need to take out personal travel insurance for injury and belongings.
  • Uniform: T-shirts are provided for working hours. Please provide your own clean, presentable, suitable shorts.
  • Day Off: Flotilla working patterns are detailed at interview.
  • Holiday Allowance: You will receive a set number of holiday days, dependant on the length of your contract. Flotilla staff may not be able to take this during their season and so can take it postseason or opt to be paid accordingly. 
  • Travel to Work: Transport options are provided for all staff working outside of the local area.
  • Watersports Equipment: All staff have free access to all watersports equipment, in line with the Company safety policies and procedures.  
  • Yacht Use: All staff have free access to yachts when booking availability allows and in line with the Company safety policies and procedures.
  • Hotel facilities: All staff have free access to our beach club facilities such as swimming pools and table tennis.
  • Staff Discount: All staff receive a discount on food and drink at our Beach Clubs.
  • Activity Discounts: All staff receive discounts at our local partners for activities such as Scuba Diving, Waterski, Wakeboarding and Yoga.
  • Friends and Family Discount for Trek Holidays: F&F discounts are available for use outside of peak season.
  • Mystic Watersports Discount: All staff are entitled to 40% off RRP on Mystic Watersports apparel if purchasing through our Trek discount process.
  • Training: All staff receive a comprehensive induction on arrival to ensure you are confident and happy in your job role. Throughout the season you will be offered further training and development opportunities.
  • Training Bursary: All staff automatically qualify for a £50 training bursary towards job-related courses. In addition, all staff have the opportunity to apply for a 50% ‘grant’ for promotion related courses. This grant is only applicable to job related courses which help support the company aims.
  • Bikes: Bikes are available for the duration of your contract. They are very basic but good enough to get around the local town on.
  • Job Swap: As part of our commitment to staff development we offer hard working staff the opportunity to sample different job roles throughout the season when operations allow. 

Personal Qualities

Whilst enjoying your work and the lifestyle that comes from living in Greece, you must always be respectful of those around you. This includes your teammates, our guests, our hotel staff, our competitors, your local neighbours and the local community as a whole. We are very fortunate to live and work in such a beautiful part of the world. We are very lucky to be welcomed into the local community. As such we only employ staff that we feel are mature enough to embrace the instructor lifestyle without causing upset or offence to our local friends and neighbours. If you are a mature, hard-working, enthusiastic and fun instructor, with a passion for watersports then we’d love to hear from you. 

We pride ourselves in offering our staff a different experience.  If you want to experience living in Greece and immersing yourself in Greek culture in a small community, you will love this job.

Please bear in mind that this job is suitable for someone who is happy to work within a small team, sometimes unsupervised.  As well as working with our English team, you will be working alongside the local Greeks. Independence and maturity are therefore essential.


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