Tom Saunders managed to condense his one-week Silver Sail program into an hour and a half lecture on the secrets to winning races. There were a few themes he returned to throughout the talk, and these will be bolded throughout this post. The class then hit the water for some practice working on what Tom described.
Keep it simple, focus on the basics. Tom laid out an anecdote about how how he and a buddy were able to place well in a national regatta with a beat up boat that had been sitting under a cottage for 30 years, just by making sure the sheet and vang tensions were right. Don’t worry about the little stuff until you’ve got the basics nailed.
Tuning. Rig and boat tuning were covered in an earlier session of the Advanced Sailing Skills course. Make sure your sail controls work and that things are tensioned the way they are supposed to be, and you’ll have an advantage over all the jokers in the fleet who just rig up and go. You don’t have to be adjusting the cunningham by millimetres 6 times a leg, but making sure your shrouds, centreboard, vang and sheets are working together is a huge step forward. Also, proper rig tuning lets you point higher on the upwind legs, and we’ll soon see how important that is.
The start. You won’t win a race on the start line, but you sure as heck lose a race there. A good start means you have clean air, and can go where you want to go. A bad start means you have reduced options, and are trying to sail in the slow turbulent air that other boats are leaving behind.
Tactics – be able to justify your actions. When doing something, think about why you’re doing it. Instead of starting a race “somewhere on the start line”, think about “should I start in the middle of the line, at the starboard end, at the port end?” Have a plan. If you’re on a leg, think about “why would I tack now?” and what advantage it buys you. Think about “why would I delay tacking?” and what advantage that buys you. When you think about doing something, being able to justify it to yourself is much better than tacking “because I was told I should be tacking more”.
In similar boats, with sailors of similar skill, you will never be able to beat someone by following them on the same tack. If the person ahead of you is on starboard tack, you’ll never be able to pass them on starboard. Any gust will hit them first. Any wind shift will affect you both the same. Any attempt to pass them to leeward will put you in their wind shadow. Tacking onto port may or may not be the right move we’ll go into (the “whys” later) but you can’t expect to beat them on boat speed alone. This is especially true near the end of a race (if you weren’t able to pass them over the the last 6 legs, why do you think you can do it in the last few hundred feet?)
The act of tacking onto the same tack as the person behind you is called “covering”. Here’s an example (because I love this video). It’s from the 2015 Laser World Championship. The boat in second place (USA, Chris Bernard) knows that he can’t beat the boat in the lead (Australia, Tom Burton) while they’re on the same tack. Tom repeatedly tacks his boat to cover Chris, denying Chris the opportunity to pass. Chris immediately responds by tacking, forcing Tom to tack again. This is called a “tacking duel”. You generally won’t get into tacking duels at club races, but you’ll see them at higher level events. At 6:07 of the video, Chris (behind) fakes a tack. Tom tacks his boat (thinking that Chris is tacking) and Chris is able to gain ground. Tom realizes his mistake, and changes tactics from covering-Chris to just making a dash for the finish line.
One final general tip is to watch the race leaders. People like Steve, Carla, Ken, the other Ken (and too many others to name), will often be at the front of the fleet, with the rest of us wondering what we’re doing wrong. So, if you see the leaders all heading the to left side of the course, start thinking about why that is. You don’t have to follow them, but it helps to figure out what they know (and that’ll help you make better decisions).
Starting Notes
We’ll talk about some properties of the start line before talking about how to execute a good start.
The sag (aka scoop, or dip) of a start line
On the water, it is HARD to judge where the start line actually is. This leads to boats near either mark being close to the start line at the gun, but those closer to the middle of the start line tend to be a little farther back. How hard is it to judge where the start line is? Well, I’m going to go out on a limb, and say Olympic sailors are better than most of us. And here is what the start line at the 2012 Olympics looked like 3 seconds before a race:
You see the boats how in the middle of the start line are farther back? This is known as “sag” to the start line. So, assuming you want to start in the middle of the line, how can you get the best position?
One way is to assume that the sag is there, and just be out in front of everyone. This takes a lot of guts. If you overestimate the sag, you’re over the line early, and have to restart (or are disqualified).
Is the start line square – which end is favoured?
By “square” I mean square to the wind. Let’s say the start line (and course) was set, and then the wind shifted 30 degrees. If the wind is coming from the starboard side of the course (for example), the “distance upwind” from the starboard end of the start line (the “boat end”) is less than the distance from the port (“pin end”) of the start line.
Generally speaking, if you put your boat perfectly in irons, it will point towards the favoured end of the line.
The other reason one end of the line might be favoured over the other is that maybe the wind is different on one side of the course. In the image below, a racer sees a heavy air gust on the starboard side of the course. They might select the starboard side of the start line so they can tack immediately after starting, and sail to the gust. Once there, they may choose to tack back onto starboard (the edges of gusts tend to be faster than the middle of gusts, so in the diagram, the sailor is trying to ride the edge of fast air)
One thing that Tom stressed throughout his presentation was having a reason for everything you do. Here are some reasons you might select one end of the start line over the other:
- You want to tack onto port immediately to get to the right hand side of the course — start at the starboard end of the line
- One end is favoured — start there
- You can’t decide which end of the start line is favoured — start at the middle of the line
- There is a large clump of good sailors at the favoured end, and you don’t want to get caught in the scrum — start in the middle
- You have trouble judging sag — start at one end of the line
All this is to say is that there are lots of things to take into account when picking a spot on the line. It’s up to you to weight the different options and to pick a spot deliberately, and execute your plan. Don’t just start “somewhere” on the line, start from where you think you can have your best race.
Starting Techniques
Before I start writing about some of the potential techniques you can use to start, I’m going to write a bit about the end goals. The best case scenario for a start is to cross the start line, with the boat at full speed, into clean air, and with right-of-way over nearby boats, just as the race starts. Now, that’s a lot to remember, and harder to get right.
Crossing the line at the right time
This is conceptually the easiest thing to get — you don’t want to cross the start line before the race starts (the best case scenario is that you have to turn around and cross again). But you don’t want to start the race late either.
So whatever technique you use to start, you want to be very close to the start line as the race starts.
Crossing the line with speed
Even if you’re first across the start line, if you’re moving slowly at the start, then someone slightly behind you (but moving fast) can pass you. So the second thing we have to think about is how to ensure the boat has some speed before we cross.
We know that reaching is a faster point of sail than close hauled. We also know that close hauled moves us upwind. This suggests that a good start technique might be to sail close to the start line some time before the start, and sail on a close reach or broad reach in the seconds before the start. The amount of time it takes your boat to reach top speed will determine how long you have to reach for. Once your boat is at full speed, you can turn it up to a close-haulled course just as the race starts, and cross the line with lots of speed. The issue with reaching in the few seconds before a start is that you have to have the space to pull it off, which is why you have to be very careful about other boats and who has right-of-way over whom.
Right of way
Here is where things get complicated.
So far we’ve determined that we want to be near the start line, reaching just before the start, and we’re going to turn upwind to close-hauled just as the race begins. But there are going to be a bunch of other boats trying the same thing. How do we ensure there’s no one in our way (and, to a lesser extent, can we give ourself and advantage by getting in the way of other people)?
Let’s look at the Racing Rules of Sailing, specifically rules 10, 11, and 12, and how they apply to 3 different set of boats:
10: When boats are on opposite tacks, a port-tack boat shall keep clear of a starboard-tack boat.
11: When boats are on the same tack and overlapped, a windward boat shall keep clear of a leeward boat.
12: When boats are on the same tack and not overlapped, a boat clear astern shall keep clear of a boat clear ahead.
Given rule 10, it’s obvious that (everything else being equal) we would prefer to be on starboard tack at the start. This means that we have right-of-way over everyone on port tack. In the diagram below, scenario 1, the green boat is on starboard tack, so she has right of way over the red boat on port. The port tack boat must do whatever to avoid the starboard boat. If you’re the starboard tack boat, it’s customary to yell “Starboard!” to let red know that you are there, and have right of way (but it’s not a rule, they should be watching where they’re going)
Rule 11 means that if two boats are overlapped (that is, part of the “behind” boat is in front of the transom of the “ahead” boat) then the boat that is to leeward has right-of-way over the boat to windward*. In scenario 2 below, both boats are on starboard tack, so rule 10 does not come into play. The boats are overlapped. Because the boats are on starboard tack, the green boat (on the port side of the red boat) is considered the leeward boat. Thus, red, must avoid green (even if it means crossing the line early, or tacking onto port). If you’re the green boat, it’s customary to yell “Up! Up! Up!” to tell red that she must head up to avoid you.
Rule 12 is pretty intuitive — you’re not allowed to bash into the back of someone else’s boat (scenario 3). Note that because the red boat has not crossed the imaginary transom line the boats are not overlapped. Red must stay out of green’s way. Red could maybe make a choice here. If she were to bear off, she could maybe establish overlap with green. Then rule 11 comes into effect, and green would have to avoid red. If red were to do this, she’d risk getting caught in green’s wind shadow. Alternatively, red could try to sail up above green. Green would maintain right-of-way but red could try to get into some undisturbed air and maybe beat green on speed.
Start strategies
The reaching start
This one is very easy to do if there are a small number of boats racing. We’ll assume that you’re the only boat, for now. The idea is to go on a beam reach, from one end of the start line to the other. This ensures good position (you’re right behind the start line) and good speed (you’re on a beam reach) when the start sound goes off. You also have a good window of time to pull off the start.
Let’s say that you time your run along the start line at 45 seconds. If you start your run (pass one of the end-points) at about 22 seconds before the start, you’ll start exactly on time, right in the middle of the start line. If you make an error in your approach (or the wind speed changes, or something) you have a very large margin of error — even if you’re 20 seconds early (or late) you still are able to pull off your perfect start.
The reaching start version 2
Let’s say there are multiple boats racing, all who are trying to pull off the reaching start (note — this happens frequently at KSC). Let’s assume that all the boats are about the same speed when they’re reaching (i.e. you won’t be bumping into anyone going the same direction as you). In this case, all you have to worry about are boats coming the other way. No problem! Instead of crossing “any one of the start line endpoints” 20 seconds before the race, make sure you cross the right-hand endpoint 20 seconds before the race. This means you have right-of-way over anyone coming from the other direction (you’ll be on starboard tack, they’ll be on port).
In the diagram, there are a bunch of boats reaching along on starboard tack (green), and a bunch on port (red). The port-tack boats have to turn to avoid the starboard ones, and the starboard boats have a nice lead when the race starts.
The “Timed start” – defending against a reaching start
Let’s say that there are lots of boats doing their reaching start, and they’ve all gotten good enough so they’re on starboard tack. Let’s say the start line is starting to get crowded, and it’s tough to find a place in the line of boats all reaching along.
The Timed start is trickier to pull off, but if you do manage to pull it off then you get to start nicely while also throwing a wrench into the plans of those who are trying a reaching start. It takes advantage of rule 11 to be the leeward boat over anyone reaching along the start line.
To execute the timed start, you must know how fast your boat can go from some point below the start line, to the start line. You start below the line at the predetermined time (say, 45 or 30 seconds before the start of the race) and head to the start line on a close hauled starboard tack course. As you approach the start line, you can start enforcing your rights under rule 11 (“Up! Up! Up!”).
The boats attempting to do a reaching start are forced to avoid you, since you’re the leeward boat. They have a few options — try to head up (which might force them across the start line early), bear off and go around your stern (costing them time and distance right before the start), slow down to the point where they won’t hit you (costing them speed at the start), tack onto port (costing them time, distance, and potentially putting them over the line, etc)
The diagram shows what might be happening 20, 15, 10 and 5 seconds before the start. Green is enforcing her rights and forcing red to make a tough decision.
The tricky part about a timed start is getting the timing right. If you’re slightly early, then you can bear off just before the start line and burn a few seconds (assuming you have room). If you’re slightly late though, then you end up starting well behind everyone else in the fleet.
The “Vanderbilt start” — A refined Timed Start
A variation of the Timed start is known as the Vanderbilt start. You pick where you want to start on the start line, and put your boat there, on port tack, about 1 minute before the start. At the 1 minute sound, you bear away downwind on a port broad reach for about 20 seconds, gybe onto starboard and head up to close hauled (takes about 10 seconds). The starboard tack approach to the start line takes about 30 seconds, meaning you pulled off the perfect timed start, and started exactly where you wanted on the line! Because all boats and crews are a bit different, the timing should be considered a guideline only, and you should work with your skipper/crew/boat to fine tune the numbers (maybe you start your gybe at 22 seconds, or 18 seconds after the 1m warning, for instance).
One final note about the Vanderbilt (or timed) start — I’d recommend using it when there are steady winds. If there is a lull (or gust, or wind shift) in those 20-30 seconds before you hit the start line, then your timing will be way off (either early or late).
The held position start
This one is the toughest to pull off. It’s a great technique in a Laser, or other boat which can be accelerated quickly, but you won’t see many keelboats trying it. Furthermore, it’s best done in a big fleet when there are too many boats to pull off another start.
The idea is that you stop your boat on (or just behind) the start line, on starboard tack, but slightly in irons. Anyone trying a reach has to avoid you (they will either be on port, or will on your windward side). If you can hold position until a few seconds before the start, you can bear off and accelerate the boat just as the start sound goes. If someone tries to come in on your leeward side, you can defend by bearing off and getting in front of them before they get their nose ahead of your transom. This is called “defending”. Note that defending will move you slightly leeward along the start line, so make sure you have some space (and defend that space)
The held position start is a game of cat and mouse where you’ll be tested on your ability to hold a position without drifting, be able to anticipate what others are doing, and be confident enough in your ability to enforce your rights. In big regattas where 50 boats are on the start line, everyone is trying to get an edge on everyone else, there is a lot of shouting from boat to boat (“Up! Up! Up!”, “You’re not overlapped!”) Often, the veteran sailors will “pick on” a new sailor after identifying them as a “marshmallow” (or “soft target”) who isn’t going to defend their start position. Not nice, perhaps, but…
Anyway, now that you know what the folks on the start line are trying to do (between defend, and ensure they have a bit of space to leeward), you can make sense of what the boats are doing in videos like this:
Dip start (not when black/U flag)
Before we talk about the dip start, I should mention the black-flag/U-flag rules. In a big competitive race, sometimes it’s tough for the RC to identify all the boats who are across the line early. If they can’t identify everyone, they’ll abandon the race, and restart. This gets old REAL quick when you have to start a race six times. So they made the black-flag. If the black flag is flying from the RC boat before a race, it means if you’re over the line early (technically, if you’re in the triangle formed by the start line and windward mark less than 1 minute before the race) then you’re disqualified — you’re not allowed to turn back and cross the start line again. That’s a huge incentive to not start early. The U-Flag is similar (slightly different rules apply if a race is restarted, but basically “if you’re over early, then you’re out”).
So, the dip start. Instead of reaching back and forth just behind the start line (where everyone else is, or is lining up), you can be reaching back and forth in front of the start line. Pick a spot that is free of competing boats, and “dip” behind the start line just before the gun goes. Obviously, you’re not allowed to do a dip start when black/U flag is up, but you can try if only normal flags are showing. This lets you sail in clean air and lets you pick a spot in the start line where there are holes. I’ve never had the guts to try to pull this off, so I can’t speak to how hard it is, or how well it works.
Windward legs
Generally speaking, upwind legs are about minimizing the distance sailed. There is an exception to that rule, but I’ll leave that to the end of this section.
Minimizing the distance sailed is important because most boats on a close hauled course will be traveling at close to their hull speed. I’m not going to talk physics, but generally an Albacore will go the “about” same speed upwind in 10 knots, in 15 knots, or in 20 knots of air, and about the same speed whether the sails are trimmed “perfectly” or “just okay”. The perfect sails and higher wind will go slightly faster, but we’re not talking a huge difference. The difference between a good sailor and a great sailor is the great sailor will be able to sail the minimum distance at the same speed. This mean tactically choosing a shorter route, and making sure that your boat is pointing as well as as it can.
Pointing
Properly trimmed sails allow you to point close to the wind. If you try to point too high, you’ll start to “pinch” and the boat will slow down drastically. If a boat with proper set sails is racing against a boat with poorly trimmed sails, they might be able to point 5 degrees higher than the poorly set boat before loosing power. To make up some angles, let’s say that one boat can point 30 degrees to the wind, but another can point 35 degrees. The boat that sails at 35 degrees will end up sailing about 40m farther than the boat sailing 30 degrees from the wind over a 1/2 km windward leg. So the first thing to do to minimize distance sail is make sure your boat is set up to point well. Get the foot and leech of the jib tensioned right, apply the right amount of vang, and start making your way upwind.
Headers and Lifts
You can’t sail right into the wind. When the course is square to the start line, this means you can’t sail straight to the mark, you have to be tacking back and forth to make your way there. But the wind is oscillating slightly left and right from the average direction, right? This means that sometimes a close hauled course on one tack is “more” at the mark than a close hauled course on the other tack.
When the wind is coming from one side (let’s say the starboard side of the course) then you can put your boat on a starboard tack and travel in a straight line (or closer to a straight line) toward the mark. This is called a “lift”. When the wind shifts to the other side of the course, and is more coming toward you, it’s called a header. A header on one tack is a lift on the other, so it make sense to tack when you’re being headed. Remember what we said about 5 degrees of difference saving you several boat lengths? Well an oscillating wind might be shifting through 45 degrees (or more) or arc, so image how much distance you’d save if you could exploit that!
So, to minimize distance sailed, tack on headers, ride the lifts.
How do you know when you’re being headed, or being lifted? This is a tricky one. Top level sailors have a hard time figuring it out. A compass on the boat sometimes helps. If you know the course is set so the prevailing wind is blowing from (let’s say) 60 degrees, you might expect your boat to be pointing either 30 degrees or 90 degrees (depending on which tack you’re on). If you’re on a close hauled course between 30 and 90 degrees, then you’re being lifted. If you’re close hauled course is less than 30 degrees, or greater than 90, then you’re encountering a header, and should probably tack. This is an example, how close you can actually point is dependent on the boat, on your sail trim, etc.
Another way to tell is to watch the rest of the fleet. If it looks like those on port tack are sailing better, then tack onto port. If Steve (probably the best racer at KSC) hits a gust and immediately tacks to starboard, then be ready to tack to starboard when that gust hits you, because it’s probably a local wind shift.
Sailing when no tack is favoured
If the wind is coming directly down the course, and neither port or starboard tack is favoured, then you can choose which tack you’re on for tactical purposes. I won’t get into covering too much, but remember what I said earlier about having a plan? Look at the situation and decide if it’s more advantageous to be on port or starboard.
In general, one wants to sail near the middle of the course. Some people will sail way off to one side, but these people are taking a risk — they have to come back at some point, and if the wind shifts so they are headed on their way back to the course, then they’re screwed. It’s okay to sail off to one side, but be sure you understand your reasons for doing so Unless there’s a good reason to go to the edges, it makes most sense to stay close to the middle. That gives you the most options if the wind shifts to favour either port or starboard.
The starboard layline parade
Some people will hit that starboard layline very early. Others will make their way up the middle of the course, and tack onto the layline later. This often leads to a “parade” of boats, one after the other, approaching the mark on starboard tack. So when do you join the parade? Generally, as late as possible. There are two reasons for this:
- If the other boat is on starboard and ahead of you, you’ll never beat him on starboard
- It’s HARD to call the layline from far away. Even if you do call it perfectly, the slightest wind shift will screw up the layline.
Having said that, if there are lots of boats in the fleet, it might be hard to find a spot in the parade if you leave it too late — remember, you’re approaching the layline on a port tack, so all the boats on starboard have right-of-way over you. You have to aim for a “hole” in the parade and tack into it.
Check out this video — there’s a “wall” of boats on starboard tack, and the approaching boat (on port) has no rights over these. She’s got to find a hole in the line, and attempt to not be caught in the wind shadow of the fleet
Upwind strategy
1st windward leg — you’re trying to establish yourself at the front of the fleet. Tack on headers, don’t be afraid to take risks, and hit the starboard layline as late as possible to reduce the chances of over-or-undershooting the mark.
2nd windward leg — be a bit more cautious. Weigh chasing that boat in front of you vs defending your position against the boat behind you. Still tack on headers, but be careful about giving the boat behind you opportunities to make gains.
Last windward leg — unless there’s a really good chance of you catching him, don’t go for the boat in front. Defend your position against the boat behind.
A note about upwind sailing in exotic boats
Earlier I had mentioned that windward was all about minimizing distance. That’s true in the vast majority of cases, and all KSC boats. There are a few exceptions though. Some exotic windward planing hulls or foilers (29er, 49er, International 14, RS700, MPS, 18′ Skiff, Moth, etc) can sail upwind faster than their hull speed, given enough wind, and they may choose to sail a longer route if it results in significantly higher speeds. KSC doesn’t own any of these boats, so don’t worry about it. I only include this note because I can’t say “it’s always about minimizing distance” when there are exceptions to the rule.
Downwind legs
If upwinds are all about minimizing distance, downwinds and reaches are all about maximizing speed. This generally means getting the boat up on a plane, and keeping it there. A boat in 20 knots of air will go much faster than a boat in 10 or 15 knots of wind, so you’re better watching for gusts on the race course, and making your way towards those, if you can hit them. If you’re faced with the choice of sailing slightly longer distance at a higher speed, take the higher speed.
Reaching legs
Most sailors, after rounding the windward mark, tend to sail too high initially, and then have to do a deeper run as they approach the gybe mark. This is slow not only because it’s a long distance, but they might not be making best use of the gusts/lulls to maximize speed.
Let’s look at red’s path. They round the windward mark, and feel the boat accelerate on a plane. They think “wow, this is great” and ride the beam reach plane for as long as they can, until it becomes obvious that they have to bear off toward the gybe mark. As they do so, the boat falls off it’s plane, and slows significantly. By this time, the boat has no choice but to continue to head down toward the mark.
Blue’s path is different. It establishes a plane, but bears off early as much as it can while staying on the plane. When a gust hits, the boat can be headed more directly downwind while maintaining the planing speeds. This lets the good sailor maximize downwind distance traveled during the gusts. When the gust ends and a lull is encountered, the boat can be headed up onto a beam reach. This fastest, most powerful point of sail while hold the plane and maximize speed as they eat up the horizontal portion of the course. When the next gust hits, they can steer for balance, and push the boat deeper again, still at huge speeds. They zig-zag along, probably doing about the same distance as red (although in an “average” more direct line) but at planing speeds throughout the leg, instead of only for half of the leg.
The above path of blue just takes into account wind speed changes. There will be wind direction changes as well that a good sailor will attempt to exploit. The key is to maintain your plane and maximize speed.
Direct downwind runs
Most boats sail faster downwind by going on a broad reach, gybing, and going on a broad reach on the opposite tack. Tasars, catamarans, 29ers, Bytes, etc typically do this. A notable exception to the rule is that Albacores tend to sail slightly faster directly on a run. I don’t know why, but that’s what the Albacore experts tell me. Lasers used to be considered faster reach-to-reach but modern Laser technique (which I’m not going to get into) is more about waves than wind, so be aware that those top Laser folks are going to be doing some crazy stuff on the direct downwind legs.
Boat-on-boat tactics
Boats sailing close to each other interfere with each others’ wind. There are two positions you generally don’t want to be caught in — stuck in the wind shadow of another boat, and being lee-bowed by another boat.
A wind shadow is pretty easy to conceptualize — the air hits the sail of the boat in front of you, and is therefore slower, more turbulent and possibly in the wrong direction for boats behind. This is sometimes talk about as “eating the other boat’s dirty air” or “the other boat is throwing junk” or some other terms like that. In general, the lighter the wind, the bigger the wind shadow is. That’s because the turbulent air has less clean air flowing around it to smooth the wrinkles. I’ve heard that a typical wind shadow is cast about 4-times-the length-of-the-boom behind the boat, but that may be just an anecdote and I have not seen any proof of that measurement. Take that advice with a grain of salt.
The 2nd situation, being “lee bowed” is tougher to explain. As a sail encounters wind, the direction of air flow is directed to follow the curve of the sails. But air is also “sticky” and it’s not just the air that hits the sails that is deflected — the nearby air is also turned. If you’re slightly behind a boat, you’ll find that the wind you do feel is more “head on” than you expect. That’s the result of the boat in front bending the air flow. And what do we know about headers? They suck! You’ll lose power since you now appear to be pinching (as far as your sails know).
Now that you know where not to be, you can judge what the boats around you are doing and attempt to avoid those situations (or, even better, but them into those situations)
Resources
Tom, who gave the talk, wrote a book about all this stuff for the old “Silver Sail” standard, although it was never published. He put the book on the KSC web site. Note that the parts of the book that deals with how to use rules to your advantage is out of date (the rules were greatly overhauled since it was written) but the “how to tune your boat” and “how to make it around the course fast” parts are great. http://kanatasailingclub.com/wp-content/uploads/2014/06/Basic-Racing-Skills-Silver-Sail-manual.pdf
The Racing Rules of Sailing published by World Sailing contains all the technical rules about participating in a race. You don’t have to know this document, but it’s a good reference. It’s updated every 4 years (after the Olympics). http://sailing.org/documents/racingrules/index.php. Inside the KSC club house there is also the book “Understanding the Racing Rules of Sailing” (which covers the 2013-2016 set of rules, which is pretty close to the 2017-2020 rules). This book is quite good at not only listing the rules, but going into situations when they might apply and understanding what each boat’s obligation under the rules are.
In physical book form, Frank Bethwaite (Olympic coach, and also the guy who designed the Tasar, the fasted monohull in the KSC fleet) wrote High Performance Sailing, now in it’s second edition. https://www.amazon.ca/High-Performance-Sailing-Frank-Bethwaite/dp/1408124912. You can also talk to Jason and he’ll lend you his copy. The sequel “Higher Performance Sailing” is good too (again, talk to Jason).
Online, YouTube is your friend. For Laser sailors, I also recommend Doug Peckover’s blog Improper Course which contains lots (and I mean LOTS) of tricks and tips for sailing the Laser. Also check out Dick Tillerman’s Rules of Laser Sailing.