Dmitry Shteyn — Choosing a Side: Developing Your Strategy for the First Beat

Navigating the first windward leg requires more than just boat speed; you need a clear plan for which side of the course offers the best tactical advantage.

By Dmitry Shteyn4 min read
Choosing a Side: Developing Your Strategy for the First Beat

Key takeaways

  • Prioritize sailing toward 'pressure'—areas of darker water or more wind ripples—over chasing minor shifts.
  • Identify the 'long tack' toward the mark and stay on it early to minimize distance sailed.
  • Account for geographic wind shadows on inland lakes and thermal draws on the Great Lakes.
  • Maintain clear air; a theoretically slower side with no traffic is often better than a fast side buried in a crowd.

The First Beat Mental Map

When we leave the dock at the South Shore Yacht Club here in Milwaukee, the first thing I tell my students is that the race doesn't start at the horn; it starts twenty minutes before. The first beat—the initial leg from the start line to the windward mark—is often where the podium is decided. If you pick the wrong side and the fleet splits, you can find yourself a hundred yards behind before you've even settled into your hiking straps.

Developing a strategy for the first beat is about reducing variables. We aren't just guessing; we are looking for evidence to support a decision to stay left, go right, or play the middle. In my experience, the sailors who consistently reach the weather mark first aren't just lucky—they have a system for reading the water.

Watching the Horizon and the Clouds

Before the five-minute warning, you should be sailing upwind. Take a long look at the horizon. On Lake Michigan, we often see thermal effects. If the clouds are building over the land toward Oak Creek, there might be a draw that favors the left side of the course (looking upwind).

Conversely, if the water looks darker or has more texture on the right, that’s where the pressure is. In sailing, pressure is king. I would rather be in more wind on the wrong tack than in a lully hole on the right tack. During a recent Tuesday night race, the fleet split evenly. Those who noticed the darker ripples coming from the northeast—even though the wind was currently out of the north—tacked early to the right. They caught a ten-degree header that allowed them to tack back and cross the entire fleet on port.

The Geographic Advantage

On inland Wisconsin lakes, like Lake Pewaukee or Lake Beulah, picking a side is often dictated by the shoreline. Trees, hills, and buildings create wind shadows and funnels. If the wind is coming over a high bluff on the right side of the course, you can expect a large "no-go zone" of dead air under the hill. However, just past that bluff, the wind often fans out, creating a lift.

In these environments, my rule of thumb is to look for the "long tack." The long tack is the one that points your bow most directly at the mark. If the mark is slightly to the right of the wind direction, the starboard tack is your long tack. Generally, you want to stay on the long tack early in the beat. If you find yourself heading away from the mark on a short tack, you are giving away distance.

Managing the Fleet and the Rules

Your strategy for picking a side must also account for the other boats. Even if you think the right side is better, if twenty boats are heading right, you might get forced into "dirty air." Sometimes, the best side is the one where you have clear lanes to sail your own race.

Remember Rule 10 (On Opposite Tacks): a port-tack boat must keep clear of a starboard-tack boat. If you decide to go left and need to cross the fleet on port tack to get back to the middle, you must ensure you have the space to do so without fouling. I’ve seen many sailors pick the right side correctly but lose all their gains because they had to duck six boats on their way back to the mark.

Concrete Example: Milwaukee Bay North-Easterly

Let's look at a typical regatta scenario in Milwaukee. The wind is 12 knots from the Northeast. The waves are building. In this setup, the right side (the lakeside) often provides cleaner wind and more consistent waves. The left side (the shore side) might have flatter water but more turbulent wind due to the city skyline.

If I see the fleet stacking up at the boat end of the line, I might start toward the pin (left) just to get clear air, but my goal is to find a window to tack toward the right as soon as possible. By getting out into the "blue water" early, I can ride the more consistent pressure and avoid the shifts caused by the buildings. The key is committing to the plan early rather than waffling in the middle of the course where you get the worst of both worlds.

Safety and Awareness

While you are staring at the wind and the marks, never lose sight of safety. In a crowded first beat, boats are converging at high speeds. Keep your head out of the boat. A tactical gain on the left side isn't worth a collision. Always have a "bail-out" plan if your chosen side turns out to be a bust. If the pressure isn't where you thought it would be, don't keep sailing into the hole—tack and consolidate with the fleet.

Written by Dmitry Shteyn — Wisconsin sailor and educator. Find more sailing notes on the daily blog or read the longer guides.