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Sailboat Racing For Beginners – 10 Top Tips

My 10 tips on sailboat racing for beginners follow some stories I have about our limited racing experiences. By default, we are sailboat cruisers – the exact opposite of racers. But even with our limited experiences, we have had major experiences. Discover how we, as absolute novices, managed to gain some wins and then read my tips at the end. Allow me to start with a story…

Sailboat Racing For Beginners

The race committee leader looked at my husband, Simon, and said,

‘In all my five years of organizing sailboat racing for beginners I’ve never witnessed your crazy tactic. It was rather brilliant but now I have to change the rules.’

Previous to owning our own sailboat we went for an annual sailing vacation with a company called SunSail. My husband and I would choose between options in the British Virgin Islands, Greece, and Turkey.

Rather than selecting a bareboat option where you simply sail around by yourself, we always chose to do a flotilla. In a flotilla, there are around ten to fifteen other boats doing the same as you all ending up in the same harbor every night. We enjoyed the social element of meeting others and it was always fun to swap stories at the end of the day.

During our week of sailing bliss, the SunSail representative would put on a friendly race between all the boats.

The informal sailboat racing for beginners was usually the day before our vacation ended.

Throughout the week Simon would weigh up his competition, play with the boat to see how fast he could get her to go and visualize winning the race. It’s sad to admit but I think one year I found him cleaning the hull of the boat to make the boat go faster!

For the particular race I mentioned at the beginning, however, Simon made a move that shocked everyone. Did we win? Yes. Was it a clean win? I’m not sure? I’ll let you decide.

Staged in the British Virgin Islands, the race was to start in a narrow area with quite a few expensive mega yachts. The SunSail representatives didn’t want novice charter boat operators losing control and hitting anything. So, the rule was that you must keep your engine on and only turn it off once you cross the start line. By doing so, the sailors could have more control over the boat.

But let me back up.

The day before the sailboat race for beginners, Simon looked at me and said, ‘I want you to time one minute.’ I looked at my phone and said, ‘Ok, I’m timing.’ Simon then put the boat into full speed and when the minute was up, I said, ‘Time’s up.’ I had no idea what Simon was doing. After a full day of sailing, I was ready for my wine, so I urged Simon to head in for the day.

Race day arrived. I don’t think any of the other boaters thought much about it, but Simon was oozing with excitement. We were instructed on timings. There would be a five-minute warning, a two-minute warning and then a one-minute warning. Then you had to cross the start line and turn your engine off just before doing so.

At the five-minute warning, we were all at the line with our sails up and flapping doing little circles. There were eight monohulled boats all varied in length.

Everyone looked like they were up for a good race.

And then to my surprise, Simon started heading away from the start line. I asked him what he was doing and he said, ‘Don’t worry. I have a plan.’ We ironically stopped at the location where he had me time him the day before. It then dawned on me why he had me time a minute the day before.

To my sheer horror, at the one-minute warning, he put the boat in full speed barreling towards the start line. All of our sails and lines were flapping all over the place. The boat was bouncing up and down with a loud revving engine. Any onlooker would wonder what the heck we were doing. We looked like the Tasmanian devil on a mission!

Ahead of me, I could see all the other SunSail boats slowly circling around the start line.

As the clock counted down, and above the roar of the engine, Simon yelled at me, ‘Kim – turn the engine off when I say ‘now’. Simon yelled ‘now’ and I turned off the engine. The wind filled up our sails and off we went.

We crossed the start line with our engine off doing seven knots. It’s as if we were a bullet-boat that shot through a line of stationary boats. I’m not sure if we looked like we were sailboat racing for beginners – we looked more like sailboat racing for morons.

The look on the other boaters’ faces was priceless. They couldn’t believe what they saw. The look on my face was sheer embarrassment. And of course, Simon had a look of absolute determination.

We won the race. We even got line honors and beat the larger boats.

Some participants said we cheated. Others exclaimed that our maneuver was priceless. The SunSail representative shook his head in disbelief. In the end, we took home the trophy.

Some races are won in the beginning. Other wins are attained at the last minute. Especially when doing sailboat racing for beginners – anything can happen!

When we raced in Greece with my parents, we won in the last 10 seconds. The race started out perfectly. We crossed the start line second and were flying along. During a tack, however, our headsail sheet got knotted up on our winch and we fell back to sixth place. We worked hard to get back to third position and then the wind died.

We had two boats close to us in the front and the rest of the fleet was behind in the far distance.

Both Simon and my stepfather started talking of defeat. My mom and I, however, said ‘it’s not over yet!’

To this day mom and I think we willed a puff of wind.

It’s as if a miracle occurred. The race finish line was down a narrow strip that leads into a larger bay. There were rocks on either side and only enough space for a few boats to sail side by side. There were three of us boats with our eyes on the end and we were behind both of them. As if by magic a gust of wind came from behind and hit our sails first. The gust propelled us forward and we passed the two boats within seconds of the race finishing. My mom said, ‘this sailboat racing for beginners is amazing!’

It was awesome. It was a magical memory. Again, we took home the trophy.

Sailboat Racing For Beginners

And then there was our biggest win ever. We entered the Antigua Oyster Regatta, an event hosting races over five days. Our boat is an Oyster. They are manufactured in the UK and the manufacturer puts on races every year in addition to organizing around the world regattas. It’s an opportunity for Oyster Yacht owners to get to know each other and see whose boat is fastest. As you can imagine it’s one big ego-fest.

The Oyster reps wanted to get family boats involved in the racing so they asked us to join. The President, at the time, even offered to bring his daughter to the race so that Sienna would have a friend. When we booked in, we were the only liveaboard family boat racing. All the other contestants had professional crew, light boats and all but one boat was much larger than us.

We were the underdogs.

Actually…I don’t even think people thought we were underdogs. I’m not sure if anyone even noticed we were there. We thought of the event as sailboat racing for beginners but everyone around us was definitely not a beginner. No one even considered that we’d place first during a race let alone win the whole regatta. Another trophy. Another miracle? Perhaps.

The interesting thing about racing is that it’s totally different from the ‘normal’ boat life we live.

On a normal day, we cruise around not particularly paying attention to our speed. We set the sails, put the automatic pilot on and read a book. There is very little adjustment. We never use our big pretty sails (spinnaker) or pay that much attention to where the wind is.

Cruising is slow, relaxing, easy-going and flowing.

Racing is fast-paced, stressing and at times extremely nerve-racking. Racing also gets your blood pumping and your enthusiasm to a near breaking point. Knowing that you can win, or beat your opponent, and having to rely on constant sail trimming, reading the wind and using a bit of tactic is simply electrifying. Even when there is light wind it’s massively intense.

And it’s not just the actual races that define the whole experience.

It’s the before and after events and ultimately the other people you’re surrounded with that solidify the overall fulfillment of a regatta or race week.

A long time ago when I was working in Cyprus, a country in the Mediterranean, and I would enjoy several amazing sunsets over the sea. Every time I watched them it was bittersweet. I could enjoy the beauty of the oranges, reds, and pinks but without having someone with me to experience the view the experience felt rather lacking. It’s not just the act of racing that’s incredible. It’s the people you’re with.

When you race you’re a team – even if it is sailboat racing for beginners. Not only do you work together to sail around the marks, but you also get to know your teammates. You eat together, you commiserate together, and you celebrate together.

Partaking in a race or a race week provides the opportunity to truly feel ALIVE.

It’s scary, it’s fun and it’s memorable. And you don’t necessarily need a trophy to enjoy the experience. If Simon has anything to do with it, however, he will go above and beyond to get a win.

Simon and ????? will be racing Britican in this year’s Antigua Sailing Week – April 26th to May 1st, 2020. We are offering a few berths to those that know how to sail (but not necessarily know how to race) and want to experience the thrill of racing in one of the most well-known race weeks in the Americas. Practice days are included in addition to a race professional to ensure the event is safe and fun.

What are you waiting for? Be spontaneous. Don’t grow to the age of 80 and look back thinking, ‘If only I said ‘yes’ more often….’

To get more information on us, our live-aboard cruising experiences, the boat, and pricing visit: The Britican Experience. Fill out the form at the end of the website and Simon will give you a call to offer more details.

Past Crew For The Britican Oyster Antigua Race Week



10 Tips On Sailboat Racing For Beginners

  1. Know the rules. There are loads of books that break down the rules of racing. It’s important to know who has the right of way, what you can and cannot do. And most importantly, how to be safe.
  2. Start on small boats (dinghies) or races for beginners. If you join a race and don’t have any help it can be very confusing and intimidating.
  3. When you’re doing your first few races, hang back and watch others. Crashes and false starts happen when you’re on the start line with all the other boats.
  4. Find a friend that knows what they’re doing. We’ve raced before where we had no clue but one person just told us what to do. He was like a conductor of an orchestra. When first starting out it helps to have someone that knows what to do.
  5. Practice, practice, and practice. Go out and fly your different sails. Race other boats around you – they don’t need to know that you’re racing them. If you see Britican anywhere near you I can guarantee that Simon is racing you 😉
  6. Be conservative with your sails. All races are different so you’ll have to see what your options are. We’ve always been able to declare if we’re going to use our big spinnaker sails or not. If we do not use our big sails it gives us a better handicap. When it’s really windy it can be advantageous not to use the big boys. We have, at times, even reefed our sails.
  7. Review the race details over and over again until you have them down pat in your head. You want to visualize the course in your head, know which way to pass the marks and clearly define any obstacles in the sailing area.
  8. When in doubt, follow another boat that knows what they’re doing. At times it’s hard to find the mark or hard to determine if you should do a long tack or do many short tacks. Find out who is the most experienced boat and do what they do.
  9. Contrary to number nine, if you’re doing really bad, consider doing something that no one else is doing. It might just work in your favor. If you’re last and everyone is doing short tacks, do one long tack.
  10. Have fun. Don’t get too serious about racing especially when it’s sailboat racing for beginners. You need to laugh at yourself and be at peace with your learning curve. Otherwise, what’s the point?

Any Other Suggestions Or Tips For Sailboat Racing For Beginners?

If yes, please leave them in the space below.

Are You Interested in Learning How To Race With Us?

Send an email to Kim@SailingBritican.com with your phone number and we’ll call you to discuss our Race Week Experiences.

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