Dmitry Shteyn — Deciding Your Upwind Direction: The Art of the First Beat

The Strategy Before the Start

One of the most common questions I get from students during our chalk talks at the Milwaukee Yacht Club is, "Dmitry, how do I know which way to go?" It’s the million-dollar question in sailing. The first beat—the leg from the start line to the first windward mark—is often where the race is won or lost. If you pick the wrong side of the course and the wind shifts against you, you’re playing catch-up for the rest of the afternoon.

Reading the first beat isn't about guessing; it's about gathering data before the starting sequence even begins. You need to look at the racecourse as a grid of opportunities and risks. Before the five-minute gun, I always tell my crew to spend ten minutes sailing upwind, away from the line, just to see what the water is telling us.

Observing the Pressure and the Clouds

In Wisconsin, especially on our inland lakes like Lake Mendota or Lake Winnebago, the wind is rarely a steady stream. It comes in puffs and patches. Your first task is to look upwind and identify where the "dark water" is. Darker water indicates more wind—pressure. If one side of the course consistently looks darker than the other, that’s usually your preferred side.

However, don't just look at the water. Look at the clouds. On a classic summer day in the Midwest, cumulus clouds act as pumps. If you see a developing cloud over the right side of the course, there’s a high probability of increased pressure or a significant shift underneath it. Conversely, if the sky is clear on the left and cloudy on the right, I’m almost always looking to head toward the clouds.

The Geographic Influence

Geography plays a massive role in picking a side. When we are racing on Lake Michigan, just off the breakwater in Milwaukee, the shoreline acts as a physical barrier. If the wind is coming from the Northwest (offshore), the land creates "bullets" of wind that fan out as they hit the water. In this scenario, the closer you are to the shore, the more shifts you’ll deal with, but they might be stronger.

If the wind is coming from the East (onshore), the breeze is usually steadier because it has had miles of flat water to stabilize. In an onshore breeze, picking a side is less about finding a secret puff and more about playing the oscillations. But if you’re on a narrow lake like Pewaukee, one shore might be high with trees and houses, creating a massive wind shadow. In that case, the "middle" is a trap, and you must pick the side with the clearest air, even if it means sailing extra distance.

A Tale of Two Sides: The Lake Geneva Example

I remember a regatta on Lake Geneva a few years back. The wind was coming from the Southwest, blowing across the narrows. The fleet was split. Half the boats headed toward the south shore, thinking they would get a lift off the land. The other half stayed out in the middle-right.

I noticed that the boats on the south shore were getting headed—the wind was hitting the bluffs and bouncing off, forcing them to tack away into headers. We stayed on the right, in the "open" water, and while we had less protection from the chop, we had a much more consistent breeze that allowed us to sail a straight, fast line to the layline. We rounded the weather mark in the top three simply because we recognized the land was a hindrance, not a help, that day.

Balancing Risk and the Rules

Once you’ve picked a side, you have to execute the start to get there. If you’ve decided the right side is favored, you want to start near the boat end of the line. This gives you the "leeward" advantage to tack early and head right.

Remember Rule 10 (On Opposite Tacks): a port-tack boat must keep clear of a starboard-tack boat. If you decide to tack to the right early, you are now on port. You must be hyper-aware of the rest of the fleet coming at you on starboard. Don't let your desire to get to the "good side" lead to a foul that forces you to do a 720-degree turn (Rule 44.1). Sometimes, it is better to duck a couple of starboard boats to get to the pressure than to force a tack in a header and lose your lane.

The Commitment Phase

Deciding on a side is only half the battle; the other half is commitment. If you decide the left is better because of a predicted shift, don't abandon the plan the moment you see one boat on the right get a small puff. On the Great Lakes, shifts can take time to develop.

Pick your side based on the pre-race data, get a clean start that allows you to head that way, and keep your head out of the boat to verify your choice. If the pressure isn't materializing, be ready to consolidate back toward the middle, but never wander aimlessly. Every move on the first beat should be a deliberate choice toward the best wind.