Steering the Best Course to Windward — a practical guide

Steering the best course to windward is one of those essential helming skills that separates competent sailors from confident ones. It isn’t just about pointing as high as possible; it’s about finding the sweet spot where heading and boat speed combine to give the best VMG (velocity made good) towards the windward objective. In plain English: point high enough to make progress upwind, but not so high that you stall the sails and crawl along. This article explains why the skill matters, how to use jib telltales to find and maintain the best course, and gives practical tips and coaching drills for teaching a new helmsperson.

Why the “best” course matters

Sailing to windward is a trade-off between angle and speed. If you point too close to the wind you may be sailing at a better angle but going slowly — so your progress toward the mark suffers. If you bear away a little, the boat picks up speed. The best course to windward is where that trade-off is optimal for the conditions: you get the most distance made good toward your upwind target per unit time.

Good helming when beating also keeps the boat safer and less fatiguing: steady steering reduces unnecessary sail trim changes, lowers the risk of broaching in gusts, and helps your crew work efficiently.

Why telltales are your primary instrument (and better than electronics for immediate feedback)

Modern instruments are brilliant — they give speed, course-over-ground, instantaneous VMG calculations, polar guidance and logs. But there are two big reasons telltales remain the helmsman’s first instrument:

1. Instantaneous airflow feedback. Telltales react the moment the airflow changes over the sail. A wind gust, a slight luff, or a change in apparent wind angle shows up on the telltale before any instrument can compute it. Instruments measure outcomes (speed, heading) and typically average or sample: there’s an inevitable processing or smoothing lag. That delay can cost you fractions of a second in gusty conditions — exactly when a prompt correction prevents a stall or surfing.
2. Direct link to sail trim and balance. Telltales live on the sail. They tell you whether the sail is working, not just how the boat is moving. Instruments can tell you you’re slow, but they don’t tell why the airflow has detached from the sail. A stalled windward telltale tells you to act before speed drops significantly.

Use electronics to confirm and quantify (VMG, speed), but use telltales to sense and react. Think: telltales for feel and tweak, instruments for review and strategy.

Feeling the boat — why sensory helming elevates your game

Great helms don’t only watch — they feel. Learning to interpret helm pressure, hull sound, heel angle, bow immersion, and acceleration is transformative.

• Helm pressure: A steady light pressure often means the sails are balanced. Sudden increases suggest gusts or too much heel; a softening might mean loss of power. Respond with the smallest practical input.
• Heel and hobby-horsing: Excessive or changing heel affects leeway and speed. Shifts in crew weight and small trim changes will show in the boat’s behaviour before instruments reply.
• Acceleration vs absolute speed: A brief burst of acceleration after bearing off indicates you can take that angle; if speed keeps falling you’re stalled.

Teaching someone to feel these things — and to verbalise them — accelerates learning. Use paired drills: one person watches instruments, the other concentrates on feel and telltales, then swap and compare impressions.

What jib telltales tell you (and how to read them)

Telltales are simple, cheap, and brilliant. A pair on the jib — one on the windward luff and one on the leeward luff — gives continuous feedback on airflow.

Basic, practical rules:

• Both telltales streaming straight aft = airflow attached, sail trimmed well for the current heading.
• Windward telltale stalls (lifts or flutters upward) = airflow separating on the windward side → sail is stalled. You are probably pointing too high or the jib needs sheeting in. Bear away slightly or sheet-in the jib until the windward telltale starts streaming again.
• Leeward telltale stalls or droops = the sail is under-trimmed for the current heading or you’re eased out too far. Sheet-out the jib (just an few centimetres) or point a degree or two higher.
• Upper vs lower telltales = sail twist clues. Use traveller/mainsheet adjustments to manage twist.

Practical helming tips to find and hold the best course

1. Start with a baseline: Trim the sails close-hauled and get a feel for boat speed. Use windward mark or compass bearing as reference.
2. Feel the boat: Watch heel, helm pressure and speed. If weather helm increases, reduce heel by easing main slightly or moving crew weight to windward.
3. Watch telltales, then the horizon: Pick a fixed point and steer to keep telltales flying — small, smooth corrections. Avoid jerky over-steering.
4. Watch for gusts: In a gust, ease the main slightly and bear off a touch; then re-establish course. Don’t try to point through gusts.
5. Trim iteratively: Make small changes — a degree or two — and observe telltales and speed.
6. Use instruments wisely: Use VMG and speedlog to confirm your eyeball and feel. If VMG falls after a change, roll it back.
7. Balance the boat: Crew movement fore/aft and laterally will keep the hull in its sweet spot.

Horizon references, wind shifts and tacking decisions (using VMG)

A constant horizon reference helps you detect wind shifts early: if the apparent wind feels like it’s lifting (you can point higher without losing speed), the horizon will show different cloud/sea patterns and telltales will behave. Couple that visual with VMG:

• Watch horizon + telltales: If the horizon suggests a lift and both telltales stream at a higher heading, your VMG may improve by pointing higher — delay tacking.
• If heading into a header: You’ll notice telltales stalling and the apparent wind dropping. VMG to the windward mark will fall. If a header persists, tack to the lifted side or wait for a favorable shift. Use short VMG checks after each adjustment: if VMG is better on the new tack, commit.
• Tack timing: Don’t tack purely because a compass bearing says so — tack when the combination of horizon, telltales, feel and VMG promises better progress on the new heading.

Coaching drills to build these skills

1. Telltale focus: Sail close-hauled. Learner watches one telltale and adjusts heading until it streams. Swap sides.
2. Feel vs instrument: Learner calls out helm pressure, heel and feel; coach records VMG. Compare impressions to instrument readings.
3. Gust response: Coach shouts “Gust!” Trainee eases, bears off momentarily, then returns to new best course.
4. VMG experiment: Two runs (higher pointing vs more speed) and compare time to mark.

Quick checklist for a windward beat

• Jib telltales: both streaming → good.
• Upper vs lower telltales: consistent → twist okay.
• Heel: moderate and controlled.
• Main trim/traveller set to control helm.
• Smooth small helm corrections; keep a horizon reference.
• Use VMG as confirmation for tacking choices.

Telltales are the boat’s voice. Electronics are the scorekeeper. Learning to listen — with your eyes, hands and body — lets you react before the instruments say a thing, then use the instruments to confirm and refine strategy. Teach a helmsperson to read telltales, to trust their feel, and to marry horizon cues with VMG, and you’ll turn competent crews into confident, efficient upwind sailors.