Skipper Partner
Project-based, Offline
We are looking for a person who:
  • Certified Sailor
    You have a skipper's license (RYA, ISSA, or equivalent) and practical sailing experience. You're comfortable navigating, handling yachts, and managing all sailing operations safely.
  • Calm Under Pressure
    Weather changes. Equipment fails. Guests get nervous. You stay calm, make smart decisions, and handle challenges without drama. Your crew feels safe because you are steady.
  • People Person
    You love hosting as much as sailing. You connect with guests, create warm atmospheres, and understand that your job is as much about the experience as it is about navigation.
  • Natural Teacher
    Some guests want to learn to sail. You're patient, clear, and enjoy showing people the ropes (literally). But you also know when someone just wants to relax and you adapt.
  • Problem Solver
    Things break. Plans change. You troubleshoot quickly, think on your feet, and don't panic when something unexpected happens. You fix problems before guests even know there was one.
  • High Standards
    You take pride in your work. The yacht is clean. The sailing is smooth. Guests feel cared for. You don't cut corners because you genuinely care about quality and safety.

About the Role

We're looking for certified skippers to captain our sailing trips across the Mediterranean.


This is a project-based role. You'll work specific weeks throughout the season, captaining groups of 6-9 guests on week-long sailing adventures.


This isn't a typical charter captain job. You're not just sailing the yacht, you're creating an experience. You're hosting, guiding, teaching, and holding space for people to disconnect and reconnect with what matters

What You'll Do

Captain the yacht

Navigate safely, manage weather decisions, handle all sailing operations. Safety and guest comfort are your top priorities.


Host the experience

You're not just a captain, you're part of the group. You eat meals with guests, share stories, create a welcoming atmosphere, and make people feel at home on the water.


Teach sailing basics (if guests are interested)

Some guests want to learn. Others just want to relax. You read the group and adapt to what they need.


Manage logistics

Coordinate with marinas, handle yacht preparation, ensure everything is in perfect condition, and troubleshoot any issues that arise.


Collaborate with Sergy and the team

Report trip updates, share feedback, and help us continuously improve the experience for guests.

What We're Looking For

Required

  • Recognized skipper's license (RYA, ISSA Inshore, IYT, or equivalent)
  • Practical sailing experience and confidence handling yachts 40-50+ feet
  • Strong navigation and yacht handling skills
  • Valid maritime medical certificate
  • Strong English (other languages a plus)

Preferred:

  • Mediterranean sailing experience (Croatia, Greece, Sicily, or Italy)
  • Hospitality or group facilitation experience
  • Comfortable working with diverse international groups
  • Passion for wellness, adventure, or transformational travel
  • Easygoing personality with strong leadership skills
  • First aid certification

What You Get

  • Competitive daily rate (based on experience and location)
  • Flexible schedule, choose which weeks you're available
  • Supportive team, you work directly with the founder
  • Growth opportunities, develop your skills across different locations and trip types

Recently completed our sailing school?


If you've earned your license through our program and feel ready for the responsibility, we'd love to talk.

How to apply

Pop Captain Sergy a message to get started

Message me
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