Advanced Sailing Practice Drills

There are plenty of lists of basic drills to teach people how to sail and race. Tack on the whistle, that kind of thing.

This isn’t one of those lists.

Instead, these are drills designed to take some difficult aspect of sailboat racing — and make it even tougher. So when you encounter that same situation on the race course, you can handle it with ease.

Many of these drills focus on the start because it’s the most important part of the race. Get a good start, and it’s hard to slip out of the top group.

Better be ready to start in big fleets!

Read through these, absorb what you can, and don’t worry if not everything is clear. All these will make more sense as we go through them on a whiteboard.

Drill 1: Inside Linesights

Setup: set marks for a starting line that’s big enough for a 10–20 boat fleet. Coach boat is on the right side of the line, facing upwind. The line is between coach’s nose and the windward side of the pin.

Action: Sailors sail slowly upwind on starboard past the coach boat, passing the coach port to port/leeward. Make sure they can cross to windward of the anchor line and don’t hook their daggerboard on it. As they go by the coach, get a linesight. Describe the linesight in as much detail as possible. For example, not “the gray house” but rather, “the second window from the left on the gray house”.

Concept: The technique above is called an outside linesight because you’re getting it from outside the starting line. It works great when the race committee boat is small. But in many regattas you’ll have a bigger committee boat that is too large for an outside linesight because you can’t see over it. So you need to get an inside linesight. Part two of the drill walks sails through how to do that.

Getting an inside lightsight on the committee boat.

Action: Sailors get onto the corner layline to the port corner of the coach boat, and sail upwind on starboard past the coach boat. They get close to the port side of the coach boat — luff sail, or if needed, do two quick tacks. Line up with the coach, and get linesight. Try to get a linesight that’s higher up on land, so that you can see it above other boats’ hulls and sails. Describe the linesight, again in rich detail.

Linsight is the right edge of the cluster of four homes on the shore.

Things to think about:

This section, and the ones below, are good questions for a coach to ask before going on the water to keep things interactive:

  • How to get as close as possible to the windward end of the line, so you get as accurate an inside linesight as possible?
  • While doing so, how to avoid hitting the coach boat?
  • Has the linesight changed, perhaps due to the coach boat swinging around on its anchor?
  • How to ensure that your linesight isn’t blocked by other boats?

Drill 2: Sharks and Marshmallows

Setup: same as Inside Linesights

Concept: So many books and articles talk about how, during the last minutes of the starting sequence, how to protect your hole to leeward from other boats — “sharks” — that try to steal it. Protecting your hole often leads to burning it up completely as you try to defend it. The easiest hole to protect is one that is so small to be unattractive — until about 20 seconds, when most/all the sharks have locked into their spots on the line.

You’re the yellow boat on the right. Shark is blue boat. They ignore your hole since it’s too small.

Action: Two minute starting sequence.

  1. With around a minute to go, you (one of the sailors) lines up just to windward of another sailor, ideally someone not very fast — a marshmallow — keeping about half a boatlength gap between them. Slowly approach the line, so your foils continue to work. Use your linesight from the previous drill.
  2. At 30 or 25 seconds, you should be a bit bow out on the leeward boat (but not over early).
  3. At 20 seconds, begin your carve up: luff boat hard and shoot up so that you get a boatlength gap between the other boat. Here’s a video of how to carve up.
  4. Then around 6–7 seconds before the start, bear off as usual to accelerate as usual.

Things to think about:

  • What’s the best technique to carve up distance on the boat to leeward? (Sculling with tiller crossing the centerline is a good way to get flagged by an umpire.)
  • When’s the best time to carve up for a given wind strength and distance to line? 25 seconds? 15 seconds?
  • As you lose forward speed by carving up, do you need to sheet in a bit earlier?
  • If you’re a boat to leeward, can you carve up hard to keep close to the boat to windward? A windward that’s too close will quickly fall back after the start, giving you freedom to tack on shifts.

Drill 3: Timeless

Setup: same as Insight Linesights

Concept: In big fleets, you never want the boats on either side to get bow out on you. (Unless you’re really sure you’re on the line.) If you see or hear them sheeting in, you sheet in so you stay bow even. In a big fleet, there’s likely to be a lot sag in the middle of the line, so it makes sense to always stay bow even since being over is unlikely.


  1. Coach asks one sailor to come by the coach boat. We call this boat the timed boat. All the others are timeless boats. The timed boat hangs onto the coach boat for a while, and the coach quietly gives them the two minute signal. No one else has the start time.
  2. The timed boat lines up to start near the coach boat. (This is because it’s easy to see when a leeward boat sheets in, but it’s harder to see when a windward boat is sheeting in).
  3. The timeless boats then approach alongside the timed boat.
  4. The timed boat sheets in to get a proper start — using their linesight and sharkproofing techniques. The other boats try their best to match her, staying bow even without being over.

Things to think about:

  • What sounds do you hear when a boat to windward is sheeting in?
  • Can you see a boat to windward sheet in with your peripheral vision?
  • What timing clues does the timed boat offer in terms of how close they are to the line, and when they start their carve up?

Drill 4: Cage Match

Setup: set marks for a really short line. One boatlength wide for 2–3 boats. Two boatlengths wide for 4–5 boats. Three boatlengths wide for 6–7 boats. Line is between coach’s nose and the pin.

Concept: During starts, often you find yourself fighting with another boat for a spot on the line. It might be the pin, it might be the boat, or just a nice spot in the middle. Cage Match helps you learn how to handle your boat to a get a good start in crowded conditions. It’s one of the best drills around for truly understanding how to effectively position your boat on the line.

Middle boat is winning the Cage Match: shutting out blue but can still lay pin.

Action: Two minute sequence. Sailors try to win the start. The line will be so short that one boat will be able to cross at any one time. Anyone that hits the committee boat or mark needs to spin a 360, just like in an actual race. Best thing to do in this situation is sheet in, sail over the line and around an end, and jibe.

Things to think about:

  • Arrive too early, your foils will lose grip, and you’ll slip to the left of the line.
  • Arrive too high, and you’ll get shut out for barging.
  • Just several feet from the boat layline is the pin layline. So if you try to hook a sailor (commit your bow to leeward of them) you might not be able to lay the pin.

Drill 5: Linezilla

Setup: super long line, big enough for 100 boats. Coach should ideally have a bullhorn or megaphone to save their vocal cords.

Concept: in big fleets and on long lines, it really easy for line sag to develop. Sailors confident in their position on the line can get a boatlength lead right at the gun, giving them clear air that lets them sail fast.


  1. Sailors get two inside linesights by slowly sailing past the port corner of the coach boat. The first inside linesight is when their bow is lined up with the corner of the coach boat, a few feet back from the line. Call this a hang back linesight. The second inside linesight should be when the sailor themselves are lined up with the coach. Call this an on line lightsight.
  2. Two minute gun goes off.
  3. Sailors head off to the middle of the line.
  4. Sailors aim to be at their hang back linesight just before they sheet in, so that they hit their on line linesight at the gun. (If there is no linesight, sailors should use their judgement — making this drill even more challenging!)
  5. After the start, sailors come by coach boat — so the coach doesn’t have to yell at them — to get feedback on how close to the line they were.
  6. Then another two minute sequence, and the cycle continues.

Things to think about:

  • Because of geometry, getting an accurate linesight, remembering it in detail (not just “gray house” but “left side of second window from the right of the gray house”), and being spot on the linesight at the start all have a big impact with long lines.
  • Big fleet starts are all about that attention to layline details.

Drill 6: Weather Mark Madness

Setup: starting line just big enough for all sailors to fit comfortably. Coach boat on the right (facing upwind), pin on the left. So, bigger than Cage Match, but smaller than Insight Linesights/Sharks & Marshmallows/Timeless. Favor the pin. Weather mark is about 3–4 boatlengths in due upwind of the coach boat; this forces boats to do at least one tack to get to the weather mark. This drill is a good one to do with drills 1–4 above, since it keeps the sailors from going too far away.

Concept: at crowded weather marks, you need good instincts to react instantly to changing situations, so you can get around quickly, while also not fouling anyone. It’s complex, but you need to act in realtime. It’s the sailing version of speed chess.

Bear in mind that the racing rules are very vague and subjective. Any time you’re in a protest, if there’s contact, it’s 50/50 that you’ll get disqualified. But if there wasn’t contact, then it’s harder for you to get thrown out.

Action: sailors do a two minute start, then round the weather mark to port and finish downwind. The entire race might take 60 seconds. Any boats that touch each other during the race are disqualified, regardless of the racing rules. So a port tacker and starboard tacker make contact — both are out. The goal is to do everything to avoid contact.

Things to think about: Lots of rules of thumb that you’ll need to learn:

  • If you start at the boat, you have starboard advantage. If you can lock the fleet (stay on their windward hip), you herd the fleet to the port tack layline. Then tack in and be first around the mark. But…
  • If the pin is so favored that a lock isn’t possible, it makes sense to start at the pin and tack onto port once you can clear the boats on your hip.
  • In general, getting to the starboard layline as early as possible is a good strategy.

This drill helps sailors instantly recognizing and master a number of crossing situations:

  • If you cross ahead on starboard, tack onto port so you lock the port tacker past the starboard layline.
  • If you’re on starboard and force a port tacker to tack, consider pinning them past the port layline.
  • If you’re ducking on port and get pinned so you can’t tack without your bow hitting a starboard boat to windward, bear away so your bow has room to swing.
  • Approaching mark on starboard, bear away to shut out anyone coming in on the port layline.
  • If you’re that guy coming on the port layline, be ready to duck, duck, duck until it hurts. And luff so you don’t hit anyone rounding the mark.
  • Going around the mark, be sure not to hit anyone going upwind. Anticipate. Luff sail when sailing upwind, and quickly pull boom to centerline when sailing downwind.

Drill 7: Leeward Mark Madness

Setup: starting line just big enough for all sailors to fit comfortably. Coach boat on the right (facing upwind), pin on the left, just like Weather Mark Madness. Favor the pin by making it further downwind. Leeward mark is about 3–4 boatlengths in front of the line, and due downwind from the coach boat; this forces boats to do at least one tack to get to the finish line.

Concept: at crowded leeward mark roundings, it’s critical to know if you’ve broken overlap or not, to avoid getting pinwheeled, and to avoid rafting up with other boats.

Action: This is the inverse of Weather Mark Madness. Sailors do a two minute downwind start, then round the leeward mark to port and finish upwind. The entire race might take 60 seconds. Any boats that touch each other during the race are disqualified, regardless of the racing rules.

Things to think about:

  • Start at the boat — left of the fleet downwind — and you might be able to get inside overlap.
  • But if the pin is favored enough, you might be able to break overlap and round ahead.
  • If inside boat barely has overlap, it might make sense to round outside and ahead.
  • If inside boat has a strong overlap, probably better to slow down and round on their tail.
  • Rounding the mark inside another boat, you need to make a seaman-like (non-tactical rounding). Try to go not-too-wide, then tight — it hurts speed because you’re doing a narrow turn, but maintains your option to tack since you keep the boat behind from locking their bow to windward of you. And if the boat behind commits their bow to leeward of you, you can keep them from tacking out from under you.
  • Rounding behind, try to lock the boat ahead to keep them from tacking until the layline.
  • Look upwind before tacking at the leeward mark. You don’t want to hit someone.
  • When ahead on a short beat, cover cover cover! Even better: lock and cover, so the boat behind can’t tack out from under you.
  • Same rules as Weather Mark Madness apply on the last beat.

So there you have it: a few drills that will hopefully advance your boathandling and help you get to the next level. What drills do you prefer to use?

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