From Student to Instructor: Dexter’s Sailing Journey with Keep Sailing

Introduction from Freddie

At Keep Sailing, one of the most rewarding parts of what we do is watching young sailors grow in confidence and develop their skills over the years.

It has been fantastic to see Dexter progress from a student on our youth sailing courses to becoming one of our instructors. Seeing that journey from first lesson to teaching others is incredibly rewarding for our whole team.

Dexter has kindly shared his journey – from his first time in a sailing boat to becoming a sailing instructor.

Starting Sailing: My First Experience on the Water

The first time I sat in a sailing boat was when my dad introduced it to me about five years ago. I loved being on the water and I was keen to give sailing a try, however I was hesitant – it seemed like a big challenge and I didn’t know how to go about starting out.

My dad did some research and found out about Keep Sailing. We thought it would be a great idea to start there because it seemed like it would give me a smooth introduction to sailing – but would also be a fun and enjoyable experience. So he booked me onto a Stage 1 course in the summer for me and my sister, which I loved.

My biggest challenge was the heavier winds, but as I learned more about sailing, I enjoyed the varied conditions because I knew how to deal with them as I became more comfortable in the boat. That’s when sailing clicked for me.

I worked my way through each stage of the progression pathway over the next few years, and then started racing toppers before going to Topper Worlds in the summer.

Progressing Through the Sailing Pathway

Over time, sailing became more than just a summer activity.

Working through the different stages of sailing helped me develop the skills and confidence needed to sail independently. Each stage built on the last, and gradually I became more comfortable handling different boats and wind conditions.

Eventually I moved on to sailing ILCAs and 420s, which introduced new challenges and helped develop my racing and boat handling skills even further.

Taking the RYA Instructor Course

After progressing in sailing, I thought it would be great to become an instructor – so that I could be on the water in the summer, but also earn some money.

Before taking the instructor course, I needed to complete a few qualifications:

• RYA Powerboat Level 2
• RYA First Aid

Once those were done, I was ready for the instructor course.

I found the course a fun challenge. Balancing fun, safety and teaching is more difficult than I thought, but I found the different methods of balancing them really interesting to learn about. We were also able to put them into practice over the course of the week.

The most challenging part was presenting and speaking through a session plan to the rest of the people on the course. It was difficult at first, but we all improved considerably by the end of the week.

One thing that helped me was writing down some key points in a notepad. This made it much easier to remember what I wanted to talk about, rather than trying to come up with something quickly on the spot.

Although the course was tough at times, it was not overwhelming or too intense. It was well paced and gave us plenty of time to improve our skills over the five days.

Becoming a Sailing Instructor

Teaching is great fun – it’s so rewarding to see people improve and grow in their confidence when sailing because of your coaching.

It’s also a great experience to be teaching instead of learning for once.

Even though it can be scary giving a sailing lesson for the first time, there is plenty of support from the other staff who can share their knowledge and experience.

Being an instructor has helped me grow in confidence and share my knowledge with others around me. It has also given me a different perspective on sailing as a whole.

A Great Example of the Keep Sailing Pathway

Dexter’s story shows how sailing can grow from a first introduction on a beginner course into a long-term passion.

Through the RYA youth sailing pathway and instructor training, many young sailors develop not just their sailing skills, but also confidence, teamwork and leadership.

Seeing students progress into instructors is something we are incredibly proud of at Keep Sailing.

If you’re thinking about starting sailing – or progressing your skills – our courses provide a supportive and enjoyable way to get on the water.

‍


Frequently Asked Questions

How do you start learning to sail?

Most people start with a beginner course such as RYA Stage 1 (youth) or RYA Level 1 (adults). These courses introduce the basics of sailing, including steering, sail control and safety on the water. They are designed for complete beginners with no previous experience.

How long does it take to become a sailing instructor?

The timeline varies depending on how often you sail, but many sailors progress through the pathway over several years. Before taking the RYA Dinghy Instructor course, you normally need:

• Sailing experience and competence
• RYA Powerboat Level 2
• A valid First Aid certificate
• Pre-assessment sailing skills

Once ready, the instructor course itself typically runs over five days.

Can teenagers become sailing instructors?

Yes. Many young sailors progress through youth sailing courses and later become instructors. Instructor training helps develop:

• Leadership skills
• Confidence
• Teaching and communication skills
• Responsibility on the water

It’s a great way to stay involved in sailing and gain valuable work experience.

What makes sailing such a rewarding activity?

Sailing builds a wide range of skills beyond just being on the water. Many sailors enjoy:

• The challenge of learning new techniques
• Spending time outdoors
• Building confidence and independence
• Being part of a sailing community

For some, like Dexter, it even leads to teaching and working in the sport.

Can you start sailing with no experience?

Absolutely. Most sailing schools welcome complete beginners. Courses are designed to introduce sailing in a safe, supportive and enjoyable way, helping new sailors gain confidence step by step.

‍