Starting Your Journey in Delivery Skippering

Life as a Delivery Skipper
How To Get Started In Delivery Skippering?

Are you dreaming of sailing the open seas, delivering yachts to exotic locations, and getting paid for it? If so, becoming a delivery skipper might be the perfect career for you. In this detailed guide, we’ll explore everything you need to know about getting started in delivery skippering.

We’ll cover the basics, share insider tips, and provide a step-by-step guide to help you embark on this exciting journey.

Along the way, we’ll use simple, easy-to-understand language, share real-life anecdotes, and include helpful links for further reading.

What is Delivery Skippering?

Delivery Skipper Jobs
What is Delivery Skippering?

Before diving into the details, let’s clarify what delivery skippering involves. A delivery skipper is a professional who is hired to transport boats or yachts from one location to another. This could be for a variety of reasons, such as delivering a newly purchased yacht to its owner, moving a yacht to a different location for maintenance, or relocating a yacht for seasonal use.

The Role of a Delivery Skipper

How To Get Started In Delivery Skippering?

As a delivery skipper, your primary responsibility is to ensure the safe and timely delivery of the vessel. This includes:

  • Planning the route: Deciding the best and safest route to take.
  • Navigating: Using charts and GPS to steer the yacht.
  • Managing the crew: Leading a team if you have one.
  • Maintaining the boat: Ensuring the yacht is in good working order.
  • Monitoring the weather: Keeping an eye on weather conditions and making necessary adjustments.

How to Get Started in Delivery Skippering

How to Get Started in Delivery Skippering
How to Get Started in Delivery Skippering

Step 1: Gain Sailing Experience

The first step in becoming a delivery skipper is to gain extensive sailing experience. Start by spending as much time on the water as possible. This could involve:

  • Recreational Sailing: Join a local sailing club and participate in regular sailing activities.
  • Crew on Yachts: Volunteer to crew on yachts to gain hands-on experience.
  • Sailing Courses: Enroll in sailing courses to learn the fundamentals and advanced techniques.

Real-Life Anecdote: Captain Sarah’s Beginnings

Captain Sarah started her journey by joining a sailing club in her hometown. She spent weekends and holidays on the water, learning the ropes and building her confidence. After a few years, she began crewing on larger yachts, where she gained valuable experience that would later help her in her career as a delivery skipper.

Step 2: Get Certified

Next, you’ll need to obtain the necessary certifications. Most delivery skippers hold qualifications from recognized maritime organizations. The most common certification is the Yachtmaster Offshore or Yachtmaster Ocean qualification from the Royal Yachting Association (RYA). These certifications require both theoretical knowledge and practical experience.

How to Obtain Yachtmaster Certification

  1. Complete a Course: Enroll in an RYA Yachtmaster course. These courses cover navigation, seamanship, and boat handling.
  2. Log Sea Miles: To qualify for the exam, you’ll need to log a certain number of sea miles. This varies depending on the certification level.
  3. Pass the Exam: The Yachtmaster exam includes both a practical test and a written test.

For more information on Yachtmaster certification, visit the RYA website.

Step 3: Build a Network

Networking is crucial in the yachting industry. Attend boat shows, join yachting clubs, and connect with other professionals. Building a strong network can help you find job opportunities and gain valuable insights into the industry.

Real-Life Anecdote: Captain Mike’s Network

Captain Mike started attending local boat shows and yachting events. He made it a point to introduce himself to experienced captains and boat owners. Through these connections, he landed his first few delivery jobs, which helped him build a reputation in the industry.

Step 4: Gain Practical Experience

Once you have your certification, start gaining practical experience. This might involve taking on smaller delivery jobs or assisting more experienced skippers. Practical experience is invaluable and will help you build your skills and confidence.

Step 5: Create a Professional Profile

To market yourself effectively, create a professional profile. This includes:

  • Resume: Highlight your sailing experience, certifications, and any relevant skills.
  • Website: Create a professional website showcasing your services, experience, and testimonials from satisfied clients.
  • Social Media: Maintain an active presence on social media platforms like LinkedIn and Instagram to connect with potential clients and industry professionals.

Step 6: Market Yourself

To find clients, you’ll need to market yourself effectively. Here are some tips:

  • Join Online Platforms: Register on platforms that connect delivery skippers with boat owners, such as Crewseekers.
  • Advertise Locally: Place ads in local marinas and yachting clubs.
  • Leverage Your Network: Ask for referrals and recommendations from your network.

Step 7: Stay Updated

The maritime industry is always evolving, so it’s essential to stay updated with the latest regulations, technologies, and best practices. Consider taking advanced courses and attending industry seminars.

The Pros and Cons of Delivery Skippering

The Pros and Cons of Delivery Skippering
The Pros and Cons of Delivery Skippering

Like any job, delivery skippering has its pros and cons. Let’s take a look at some of them.


  1. Adventure: Travel to exotic locations and experience life on the open water.
  2. Good Pay: Competitive salaries, especially for experienced skippers.
  3. Independence: Enjoy the freedom of working independently and managing your own schedule.


  1. Long Hours: Extended periods away from home and family.
  2. Stressful Conditions: Navigating through challenging weather and dealing with mechanical issues.
  3. Physical Demands: The job can be physically demanding, requiring strength and stamina.

Real-Life Anecdote: Captain John’s Journey

Real-Life Anecdotes

Captain John started his career as a delivery skipper after retiring from a corporate job. He loved sailing and wanted to turn his passion into a profession. John began by taking on small delivery jobs, gradually building his experience and reputation. Today, he is a sought-after delivery skipper, enjoying the thrill of sailing to new destinations and meeting interesting people along the way.


Becoming a delivery skipper can be a rewarding and adventurous career for those who love the sea and have a passion for sailing.

While the journey requires dedication, experience, and certification, the potential for high earnings, travel opportunities, and the sense of accomplishment make it a highly desirable profession.

By following the steps outlined in this article, you can set sail on your journey to becoming a successful delivery skipper. Gain experience, get certified, build a network, market yourself, and stay updated with industry trends.

With hard work and perseverance, you can navigate your way to a fulfilling and lucrative career on the water.

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