6 Ways to Go Sailing and Lessons Learned
6 Ways to Go Sailing and Lessons Learned

If you’re reading this, chances are you’re already a sailor. Or maybe you’re an aspiring sailor, looking for your way into the sport.

Whether you’re new to sailing or have decades of experience, there are many different forms of sailing on offer. I’ve participated in a number of these myself, and in this article I’ll cover some of my experience with each, what to expect and how to get involved.

Dinghy Sailing

Dingy sailing is the best way to learn the basic principles of sailing. When you’re out there on your own or with just one other sailor, you need to understand the basic principles of sailing in order to get anywhere, and keep yourself out of the water.

If you’re racing, in-depth knowledge of sailing physics, tactics and racing rules is crucial in order to reach the podium. With control over every aspect of the boat, dinghy sailors get used to making quick decisions based on sailing intuition built over many hours, days and years of experience.

I started my dinghy sailing life as a 14-year-old in a summer learn to sail program in Canada. It was a great way to learn how to sail – partly because the water temperature never gets above 12 or 13 degrees Celsius, providing a lot of motivation to stay in the boat! After advancing from the learn-to-sail levels I moved on to a race training program which provided a way to practice and hone my basic sailing skills in a laser, as well as learn more advanced racing skills.

Many yacht clubs and sailing schools offer learn-to-sail programs in dinghies for children through to adults. These are a great way to learn sailing and racing skills.

If you just want to get out on the water, you can generally pick up a small sailboat at a reasonable price tag, or some places offer these for rent by the hour. If you want to race, dinghy and skiff sailing clubs are a great place to meet and compete against other sailors of all levels.

Yacht Deliveries

In my early twenties, I spent about a year living in New Zealand. Towards the end of the year, looking for something new, I decided to help with a yacht delivery from Northland, New Zealand over to Australia.

It was very exciting, but I have to admit, I didn’t quite know what I was getting myself into!

I had done lots of dinghy sailing, racing and cruising on a small keelboat, but always in sheltered or near coastal waters. I had never done a long overnight passage or ocean crossing.

Almost as soon as we sailed into the open waters off the cost of Whangarei, New Zealand, I started to feel sick. After a short time, I was extremely ill and could not bear to go down below deck for more than 30 seconds before I had to lie down, or would be sick. For the next three days, this got worse and worse. About three days in I was at the point that I felt certain I would never make it to the shores of Australia. It was the worst feeling I’ve ever had in my life.

Then, almost as quickly as the sickness had come on, it was gone! Setting off around Cape Reinga, the seas had been very rough. A few days into the trip, the seas had settled down and my body had become used to the motion of the yacht.

It was fantastic. The next few days were some of the most memorable of my life. It was my first time in the open ocean – days away from the sight of land – and there was something truly magical about that. Not to mention, the millions of stars, glimmering phosphorescence, hundreds of dolphins and multitude of other wildlife we encountered along the way.

I would definitely (and have many times), help with yacht deliveries again. It’s a great way to get away from it all for a few days and to build up your sea miles. Many people moving their yacht from point A to B welcome a few extra hands onboard to help with the voyage and are more than happy to have extra help onboard.

However, my story is a cautionary tale. For anyone looking to do some offshore sailing for the first time, I suggest getting started with some shorter day or overnight trips. The middle of the Tasman sea is not the best place to find out that yes, you do get seasick, and not have any clue how to manage it! You are also not much help to the skipper and other crew if you’re violently ill, and can in fact turn into a liability

On the plus side, if you do head out on a shorter coastal sail and find yourself feeling ill, all is not lost. I have now done thousands of offshore miles and have worked out how to manage my seasickness. At times I still suffer from seasickness, but know how to prevent it (for the most part), how to reduce its severity and how to recover; even if sick I am still very much a functioning part of the crew and certainly not a liability.

Arriving in Sydney after sailing across the Tasman Sea
Arriving in Sydney after sailing across the Tasman Sea


For those looking for a slower paced sailing experience, there is a dynamic and supportive community of cruisers all around the world.

Although most of my sailing has been racing, in 2015 I was lucky to be invited along for a small glimpse of this cruising community with a family from my home province of Nova Scotia, Canada.

The crew on SV Fluenta, consisting of Max, Elizabeth and their three kids, Victoria, Jonathan and Benjamin, already had thousands of sea miles under their belt. By the time I came onboard, they had already sailed across the Pacific and done several crossings from New Zealand to various Pacific Islands.

I joined the family in Fiji to help them sail Fluenta back to New Zealand.

While waiting for an appropriate weather window for the crossing, we sailed her out to Musket Cove at Malolo Island for a little bit of R&R.

There, we spent a fantastic few days around the island, experiencing a bit of the cruising life and hearing the family’s stories of far-flung adventures in more remote locations of Fiji and beyond.

We also met a number of other cruisers the family knew from their previous time in Fiji. One of the things that was evident is, just like the racing community, the cruising community has their own culture and network of people who are always happy to lend a hand to their fellow sailor or join in social events.

Unlike racing, cruisers tend to sail with their family and friends, which means there are fewer opportunities for crew to join in. However, many of these cruisers do want extra help for longer parts of their journey; this is a great way for crew to experience a bit of the cruising scene.

Discovering cruising - sailing on Fluenta in Fiji
Discovering cruising – sailing on Fluenta in Fiji

Yacht Racing

Although I did some yacht racing in Canada, this is something I mainly became involved in since moving to Sydney, Australia.

One of the great things about racing yachts is the accessibility for people of all ages and abilities to be involved.

Firstly, there is a very wide variety of yacht types and race types, each lending themselves to different levels of sailing ability, physical involvement and competitiveness.

Secondly, yacht owners are often in need of extra crew to join their team. For sailors, crewing provides a way to go sailing without the cost of owning or chartering a yacht. For those new to the sport, there are many skippers willing to train keen and willing crew.

Twilight and non-spinnaker club racing offers a social experience that’s easy to handle for people who are new to sailing. Sailors can then step-up to club inshore spinnaker racing, and next to short offshore or larger regattas. At the higher-end for amateur sailors, there are competitive one design fleets, state and national regattas and long offshore races – all with their own set of challenges for skipper and crew.

My early yacht racing days were in a Sonic 23 called Boreal in Canada. Sailing on Boreal was definitely on the slower, social end of the yacht racing spectrum! She is a small yacht with an LOA of only 23 feet, and comfortably sailed with two people (although can have more onboard). We only raced her under jib or genoa and main sail, and only in inshore club races.

After moving to Australia, the first regular yacht I sailed on was a Mumm 30, 2Xcess, out of Middle Harbour Yacht Club. She was a big step-up from racing on Boreal, in both speed and complexity. She raced with at least 7 but preferably 8 crew, and spinnakers. At 30 feet, the loads were a lot bigger than on Boreal, but still manageable.

Since starting out on a small, simple-to-sail yacht in low pressure conditions, I have now moved on to sail and race much more technical yachts up to 50+ feet, in competitive State, National and One Design races.

At each stage, it was a progressive step from one type and size yacht and level of racing, to the next, and there is always lots to learn at each step of the way.

Although I have moved on from my early days in Boreal, whenever I head back to Canada I still enjoy taking her out for a spin. Yacht racing isn’t necessarily about racing the biggest yachts or winning the most trophies; if you’re after something social or more laid-back, there is plenty of opportunity for that, too.

Sailing on Rush in the Balmain Regatta, photo credit Ben Williams
Sailing on Rush in the Balmain Regatta, photo credit Ben Williams

Long Offshore Yacht Racing

Although we covered yacht racing above, I think offshore racing warrants its own category here!

In my role as Founder & CEO of MySail, an app to help people go sailing, including a section for connecting potential crew with yacht owners, I am inundated with enquiries about joining a team for the Sydney to Hobart Yacht Race.

This iconic race holds a special place in the hearts and minds of sailors and non-sailors alike, as well as the prestige and respect that comes with completing one of the world’s most significant offshore races.

Before looking to compete in a race like this, sailors should have a fair bit of offshore sailing (and particularly racing) experience under their belt. Like the story of my first ocean crossing, half way across the Bass Straight in a yacht race is not the time to find out you get violently seasick, or to experience your first offshore sailing conditions.

Offshore yacht racing has its own set of challenges. During the race, yachts may be away from safe haven or emergency services for extended periods of time. Wind and sea state conditions can be much worse than those experienced when sailing inshore or in short offshore races, and crew need to perform over an extended period of time with limited sleep.

It also has its own set of rewards.

Sailors are known to be social creatures, and that’s evident when you arrive at your destination after a long offshore race. Crews revel in telling their (often embellished) tales to other competitors, and the camaraderie of this tight knit community is evident.

My first significant offshore yacht race was the 400 nautical mile Gosford to Lord Howe Island Yacht Race.

I was hooked.

It’s not that I loved every second of the journey. There were many times I felt unwell, cold and tired. It was overcoming these challenges, the camaraderie of being part of the crew and the satisfaction of completing the race that made this a memorable experience.

To me, there is something addictive about offshore yacht racing. Something that, despite the challenges, keeps me coming back for more.

Sailing on Khaleesi at the start of the CYCA Bird Island Yacht Race
Sailing on Khaleesi at the start of the CYCA Bird Island Yacht Race

Yacht Ownership

I’ve mainly focused on crewing, because this has been my primary involvement in the sport.

However, without the yacht owners, there would be no place for crew! If your budget allows, owning a yacht offers greater freedom to get involved in the aspects of sailing that interest you, and control over your program.

Many yacht owners are experienced yachtsmen and women, but many aren’t. If you’re new to the sport and want to buy a boat, there are online and in-person training courses as well as heaps of books and online materials to help you learn. You can also hire a professional sailor for some on-board training, or find some experienced crew to join your team.


Sailing offers something for everyone, so if you’re looking to get involved, don’t shy away, just get out there and sail! If you’d like to find a crewing position on a yacht, or need crew to join your team, you can check out MySail’s free crew connection service here.