The first time you take part in a sailing race can feel like an overwhelming challenge. Even if you’ve already mastered the basics of sailing, the presence of other boats on the race course can feel intimidating. It doesn’t have to be that way, as sailing journalist Andy Rice explains…


One of the best ways into competitive sailing is to crew for somebody else more experienced. This way you can focus on one thing at a time, particularly if you’re on a bigger boat. The bigger the boat, the more the tasks are spread around everyone on board. You’re a cog in a bigger system.

If you get into a double handed dinghy or catamaran, then you’re dividing up the tasks between the two of you. You’ll have more responsibilities, but this is still a good way to get to grips with sailboat racing alongside someone with more experience.

Or if you really want to throw yourself in at the deep end, then go racing singlehanded! Then it’s all down to you. This is how I got into sailing and ultimately racing, making mistakes and learning from trial and error.

SAILING RULESBefore you enter your first sailing race, you need to have a basic understanding of the Racing Rules of Sailing. You can find them here. Whilst the sailing rules can look a bit daunting, don’t be too put off. These three basic rules will see you through the majority of situations on the race course:


Another simple way of looking at this is when two boats are on a collision course, remember this: “If you ON the right, you’re IN the right!” Even though it’s not required under the Racing Rules of Sailing, when you’re on starboard it’s good practice to shout ‘Starboard!’ at the boat on port tack, to make sure they know you’re there.


If your boat is closer to the wind then you have to keep clear of a boat downwind of you (although the Port/Starboard rule takes precedence when you’re on opposite tacks).


This is sort of common sense. If more than two or more boats are side by side as they approach a turning mark, the boats on the outside have to give room to the boats on the inside of the turn.
In many situations, this rule can become way more complicated, so do look at this rule in more detail. But when you’re starting out and don’t want to get in other people’s way. Remember to give room to other boats around a busy turning mark.


There are many different types of sailing boat out there. There are literally hundreds to choose from. So which sailing class do you choose, and how do you know it’s right for you?

Well, hopefully you’ve already been sailing and got a sense of what kind of sailboat you think is right for you. The broad categories of sailing classes can be broken down into the following:

  • Dinghies: small sailboats between 3 and 6 metres long, which cost a few hundred to a few thousand dollars, typically sailed by one or two people.
  • Catamarans/ multihulls: Twin-hulled sailboats that provide more stability and also capable of high speeds. Small catamarans are typically sailed by one or two people.
  • Keelboats: because they have a heavy keel underneath the boat, keelboats are inherently more stable than dinghies or catamarans. This makes them a very safe and secure platform, ideal for beginners. But there are also higher-performance keelboats, so-called ‘sportsboats’, that are capable of planing downwind and giving you a very exhilarating ride. Small keelboats typically measure between 6 to 8 metres long and are sailed by crews of three upwards.


Course configurations for a sailing race can come in all shapes and sizes. But one of the simplest and most popular is a straight ‘up and down’ sailing course, otherwise described as a ‘windward-leeward course’ or sometimes just as a ‘sausage’! A lot of the Olympic sailing classes, as well as the America’s Cup, use this simple windward-leeward configuration, which places an emphasis on upwind tactics and strategy, and the same going downwind. Other popular sailing course configurations are the triangle or the square courses, both of which test your ability to sail on a reach, when the wind is blowing across the boat. Although there’s less opportunity for overtaking and the reaching legs are less tactical, a reach is often the best angle for peak speed and it can be fun just seeing how fast you can push the boat. Once you get on to a race course, you’ll start to understand all the different elements of sailboat racing that make it so addictive. It’s not just about pure speed, it’s about choosing the best path through the ever-varying wind pattern – the gusts and the lulls, and the wind shifts. Even when you’re racing on the same course, no two sailing races are ever the same. That’s why this sport never gets boring.


The start is often the most hectic part of the race. Make sure you’ve got a waterproof watch with a good countdown function, or at the very least, a stopwatch. Take a note of the starting sequence and what flags and sound signals are going to sound at what time. A 5:4:1 sequence is typical, meaning the Warning Signal goes up on the Committee Boat at 5 minutes before the start, then the Preparatory Signal at 4 minutes, the 1 Minute Signal at 1 minute, and then the Start itself.

When you’re sailing up to your first ever start line, sit a little way back from the rest of the fleet. Don’t try to fight for a position in the front row, not unless you’re sailing with someone who has the confidence and experience to get in there and fight for the spot. Get a sense of how the start works, and gradually move closer to the start line as your own confidence and experience grows.

Eventually you want to be crossing the start line less than a metre behind the line, travelling at full speed, ideally with good space either side of you from any other boats. But putting all these skills together takes time and patience.


Once the start is underway and the fleet is on the open race course, you can bring tactics into play. This is the art of positioning yourself for maximum advantage compared with your opponents. Sailing races are often compared to a game of chess, and the tactics you employ can be a big part of the reason why you’ll make gains during a race, or make losses if you get your tactical decisions wrong. There’s a lot more to this subject which we’ll come back to another blog where we’ll dig further into the detail of sailing tactics.


Make sure you know what the finish line of your sailing race looks like before you get on the water. Just like the start line, the Sailing Instructions will include a definition of the finish line, which is often marked with a blue flag at either end of the line. If you’re further back in the fleet, you’ll be able to use the boats in front of you to help show you the way across the finish.

If you find yourself in the lead, then congratulations! But leaders of a sailing race often come unstuck when they can’t find the finish. This is when you need to be absolutely sure of how many laps you’re racing, watching out if the Race Committee has hoisted the ‘Shortened Course’ flag if it’s an early finish, and then being able to identify the finish line from a distance.


As you can see, there’s a lot to learn every time you compete in a sailing race. If you’re hungry to develop your skills and knowledge quickly and accelerate your learning curve, then a sailing app can help enormously. Many of the best sailors in the world race with products to help log all kinds of useful information – your speed, heel angle, pointing angle to the wind, distance sailed, and so on. Want to learn more about our popular sailing app? Learn more about the Sailmon App.

One of the great aspects of using an app like Sailmon is being able to make direct performance comparisons with your friends and rivals on the race course or in a training session. When you did 6.9 knots on that windward leg, how did that compare with others on the same leg? Did anyone record 7.0 knots or more? If so, what did they do differently? Maybe their heel angle was different to yours, for example? Once you start to measure your performance, analysing the data can offer great insights into the reasons why you’re fast or slow compared with others. Things that could take years to learn, you now have the potential to learn within days or even just a few hours.

The things is, we human beings are very good at telling ourselves stories about how we showed great skill to win a sailing race, but how we were struck by terrible bad luck when we did badly. Maybe the story is true, or maybe it wasn’t? With an advanced sailing app like Sailmon, the data doesn’t lie. It gives you the truth of what happened in your sailing race, and helps point to what you did well, and the areas where there is room for improvement.


Once you’ve equipped yourself with the right boat, the right sailing partners (unless you’re sailing solo), and you understand the basic right-of-way rules as described in the Racing Rules of Sailing, you can start tackling your first sailing races.

Remember, this is a learning process that never stops. Just like when you learn any new skill – whether it’s learning to swim, to ride a bike or a drive a car – at the beginning it can always feel like there’s too much to learn all at once. Learning to sail, and then learning to race, is an overwhelming experience.

Enjoy the process, no matter how overwhelming it feels. The things that you have to think about today will soon become skills that your mind and muscle memory will do for you on autopilot. Bit by bit, sailing race by sailing race, you will get better. It’s inevitable. Commit to the process and enjoy the journey!

Look out for a lot more ‘go faster’ content coming your way from Sailmon. We’re keen to share more content on various topics that all add up to helping you sail better. Follow us onFacebook,Instagramor subscribe to ournewsletter. Whatever you do, don’t miss out on this valuable content! We’re here to make you even better than you are today!


Check out this webinar!
Dylan Fletcher will emphasize the importance of focusing on the right things long before the gun. The British Olympic Gold Medal winner at Tokyo 2020 will share his thoughts about boat preparation, weather conditions, strategy, tactics and more. A good performance during the race is essential, but a decent plan of action is more than important as well. 

Check out the preview below or subscribe here for the full recordings