David Dsilo2


Dave Dellenbaugh Sailing

David Dellenbaugh is a champion helmsman, tactician, author, coach, rules expert and seminar leader who has spent his career helping sailors sail faster and smarter.Here are the learning resources that he has created to help you improve your racing skills.

Sailing Upwind

Almost everyone knows that boats cannot sail straight into the wind. It's a nice idea, but unfortunately it doesn't fit too well with the laws of nature. Trying to sail upwind is a little like driving up a mountain.  You can't go straight up, so you have to follow a winding road, zig-zagging back and forth.

In a sailboat, the hairpin turns are called tacks. To reach an upwind destination, you have to sail as close to the wind as you can, tacking back and forth between closehauled courses on starboard and port tacks. This is one of the biggest challenges in sailing. It is also one of the most artistic. There's nothing like taking the helm on a windy day and settling into an upwind "groove" where the boat almost sails itself to windward.

How close you can point to the wind depends on your boat, as well as on wind and sea conditions. The typical square rigger, for example, could only sail about 65 degrees to the wind. This meant that from closehauled on starboard tack to closehauled on port tack was an angle of 130 degrees. As you might guess, it took these boats a long time to make progress upwind; that's why they sailed routes in the "trade winds" where the breeze was behind them most of the way.

It wasn't until the development of fore-and-aft sails that boats improved their upwind performance significantly. One of the reasons the English armada defeated the Spanish, for example, was their superior upwind ability. This enabled the English to establish and maintain positions to windward of the larger Spanish ships, which gave them a huge fighting advantage.

Today's sailboats can sail upwind better than ever. With more efficient keel and hull shapes, it's not uncommon for modern keelboats like Solings or Etchells-22s to sail 35 degrees to the wind. When I sailed a 12-Meter in the heavy winds off Perth, Australia, it was typical to sail a true wind angle as small as 32 degrees (or a tacking angle of only 64 degrees!). This angle is narrowest when seas are smooth and winds are strong.                                                                                                                                                                                               

Steering Upwind

When your destination is to windward, you have to sail closehauled, continually trying to point your boat as close to the wind as possible. This takes a bit of practice, because you can't just aim the boat for a buoy or a distant point on shore like you can at other times. And there is no magic dial to tell you when you are sailing closehauled. There are, however, a few guidelines.  

Preparation – Before you begin sailing upwind, sit on the windward rail with your hiking stick in one hand and mainsheet in the other. Have your crew hold on to the jib sheet. Now feel the wind on your body. Use the wind ripples, telltales and masthead fly to get a rough idea of the wind direction. Turn the boat so you are heading perpendicular to the wind (beam reaching).

Sail trim – Now start trimming in both the mainsail and jib so your boat accelerates. As soon as you have some speed, start heading closer and closer to the wind. Each time you head up, trim your sails in a little tighter so they stop luffing. When you reach a closehauled course (about 45 degrees to the wind), your sails should be trimmed in tightly.

Where to look – The skipper should concentrate on the front part of the jib, along the luff of the sail. If you're on a boat without a jib, such as a Laser, watch the front part of the mainsail.  You are looking for two things: 1) A bubble, or backwinding, along the front of the sail; and 2) Movement of the windward and leeward telltales on the sail.

Steering by the jib – I learned to sail upwind by using the front part of the jib as a guide. This is a good basic technique. With the sails trimmed in tight, keep trying to steer a little closer to the wind. When the front part of the jib just starts to backwind (or luff), you are sailing as close to the wind as possible.

If you head up any farther, more of the wind will hit the back of the jib and a larger part of the sail will luff. This is called "pinching." If you continue sailing this close to the wind, you'll feel the boat start to slow down. When you want to make distance to windward, continually try to point the boat as high as possible without pinching and slowing down too much.

Steering by the telltales – Another good way to know how high you can point is by watching the telltales on your jib. These pieces of yarn are usually taped on the sail about a foot back from the headstay. Start out by sailing closehauled with the telltales on each side of the sail streaming straight back. Then head up slightly. When the jib is about to luff, the windward telltales will start to lift up above a horizontal position. This is a good upwind heading. If the windward telltales get more active than this and start to spin around, you are pinching too much.
      Telltales will also indicate when you are not sailing as high as possible. If the leeward telltales start to flutter or drop out of a horizontal position, then you are sailing too low and losing distance to windward. In this case, head up until the leeward telltales straighten out and the windward telltales just begin to move again.

Practicing – Finding the upwind groove is a matter of practice as much as anything. You just have to spend time sailing closehauled, watching the luff of the jib and telltales, and constantly trying to head a little higher without losing speed. If you have a chance to sail upwind next to another boat, you'll get a quick and accurate idea of how efficient a job you're doing. Ultimately, if you can close your eyes and keep your boat going upwind, you'll know you really have the "feel".


Steering a boat on a closehauled course is only part of the challenge of getting to an upwind destination. You can sail closehauled all day, but if you remain on one tack, you are only zigging and not zagging. Making progress upwind requires sailing on both tacks.

The act of tacking, by definition, takes you from one tack (starboard or port) to the other, with your bow swinging through the wind. The sails begin to luff as you push the tiller over, they flap wildly when you are head to wind, and then they fill again as you reach a closehauled course on the new tack. Before you begin a tack, consider the following requirements:

1) Boatspeed:  First and foremost, your boat has to be moving before you can tack. If there is no water flowing over the rudder, the boat won't turn when you push the tiller over. So don't try to tack when you're going slowly. Instead, turn the boat away from the wind to fill the sails and pick up speed. Tack only when the boat's momentum is sufficient to carry her around through the turn.

2) Angle of sail:  A boat normally tacks from one closehauled course to another. If you begin a tack from a reaching course with the sails half way out, it can be difficult to spin the boat all the way through the wind without losing speed. So before you tack, trim your sails in to the center of the boat and head up to a closehauled course.

3) Room to maneuver: Tacking involves an abrupt (90-degree) turn that may not always be anticipated by other boats. So before you push the tiller over, look around to make sure you have room to tack. Remember that while you are tacking, you must stay clear of other boats.

Tacking Mechanics

Once you've got good speed on a closehauled course and have plenty of room on all sides, you are ready to tack. Here is a step-by-step procedure of everything the skipper and crew should do before and during this maneuver.

First of all, the skipper should tell the crew about upcoming tacks. Not all crews are good mind readers. I remember making an unexpected tack in one race at a recent Thistle National Championships. I had to avoid another boat and, unfortunately, didn't have time to warn my crew. When we came out of the tack, my crew was still in the hiking straps – under water on the leeward side. The moral is if your crew is not ready, a tack can end up in disaster.

To make sure everyone is ready, the skipper typically yells "Ready about?" at least a few seconds before the proposed tack. What the skipper is saying is: "I'm about to throw the helm over. Are you ready to let go of the old jib sheet, trim in the new and move to the other side?" When the crew is prepared, they should respond  "Ready."  This is a signal for the skipper to begin the tack.

When I am racing, I modify this procedure slightly. I tell my crew that when I say "Ready about," I'll assume they are ready to tack unless I hear an objection. This usually works, but in a less pressured situation I'd suggest waiting for a positive response.

Executing the tack itself is a skill that takes a little practice to perfect. The skipper's first move is to push the tiller to leeward, slowly at first and then faster as the boat reaches head to wind. While this is happening, the skipper stands up, facing forward, moves across the cockpit and continues turning so he can sit on the new windward rail. He exchanges the mainsheet and tiller behind his back just before (or as) he sits down, and then brings the tiller back to centerline as the sails fill on the new tack.

The crew's job is usually a little easier.  When the skipper says "Ready about," you should take the jib sheet out of the cleat and hold it. Then grab the windward sheet and pull all the slack out of it. Just before the boat reaches head to wind (and the whole jib begins luffing), release the old sheet (making sure it runs freely) and trim the new sheet. While you're doing all this, you must move across the cockpit to the other side.

Roll Tacks

Just as with any maneuver, tacking is more effective if you use your weight and sails to help steer the boat. In racing, the aggressive use of crew weight during a tack is called roll tacking. This technique works best for lightweight boats in light and medium winds.      

To roll tack, heel the boat a little farther to leeward as you go into the tack.  As we explained earlier, this helps the bow round up into the wind. When the boat reaches head to wind, roll it sharply to windward by hiking out hard on the rail. Just when your rear end is about to get wet, cross over to the new windward side and hike out to flatten the boat again.  You've now performed a state-of-the-art racing tack.

‘In Irons’

One of the potential pitfalls of tacking is the possibility of getting caught "in irons." This usually happens when your boat is going slowly to begin with, or hits some waves as the tack begins. The result is that the boat ends up pointing directly into the wind and stops moving forward. With the sails luffing and the boat starting to move backward, this can be a tough situation.

The best way to deal with being in irons is to avoid it in the first place. Here are some ideas. First, don't try to tack unless you have a good amount of boatspeed. Second, avoid tacking from reach to reach. Trim your sails in tight and always begin your tack from a closehauled course. Third, if the seas are rough, turn the boat quickly through the wind so the waves won't kill the boat's momentum before you're on the new tack.

If you do get caught in irons, keep calm. It will give you a good opportunity for some boathandling practice. The best idea is to encourage the boat's natural inclination to drift backward. What you want to do is get the boat moving through the water so you can use the rudder to turn the bow away from the wind. Hold your main boom out to one side (this is called "backing the main"), and push the tiller toward the boom. If you do this right, the boat will turn as if you were backing out of a parking spot.

Another way to get your bow pointed away from the wind is to back the jib. Have your crew grab the jib's clew and hold it out so the jib fills on either side. At the same time, the skipper should push the tiller to the opposite side. It's the old principle of using your sails to help steer.


One thing that scares many beginning sailors about going upwind is heeling. Boats tend to heel more when sailing upwind because the sails are angled so that the wind's force hits them sideways. Centerboard boats are tippy and heel quite a bit since they don't have much ballast to counteract the force on the sails.  However, it's also easy to flatten them by hiking out.

Keelboats won't respond as much to crew weight, but they usually have a good deal of lead in their keels so they won't tip so easily. Because of this, they offer a very steady ride. And you'll be secure knowing it's almost impossible to capsize a boat with a keel.

When a boat does heel, it can be either scary or fun, depending on your state of mind. In very light air, it's good to make the boat heel a little so the sails will sag to leeward and keep their shape.  As the wind gets heavier, however, it's better for performance and for peace of mind to sail the boat as flat as possible.

There are several reasons to minimize heel in breezy conditions:

1) If you heel too far, the boat will capsize and you'll get wet. This isn't too much fun unless it's a hot day and you're in a boat like a Sunfish or Laser that can easily be righted.

2) The further you heel, the more you sideslip because your centerboard or keel no longer sticks down so far into the water. The famous winged keel on 1983 America's Cup winner Australia II was designed with this in mind. When the boat heeled, the leeward wing actually stuck down farther into the water.

3) As you heel more and more, the rudder also becomes less effective, which makes it harder to steer.

4) Finally, heeling to leeward makes the boat want to head up toward the wind. This tendency is called "windward helm," because your helm (rudder) is trying to make the boat turn to windward. To counter this force, you have to keep pulling the tiller to windward, which means more work for you and slower boatspeed because the rudder is dragging more.

In windy conditions, sailboats have a tendency to heel more than you might want them to.  When this happens, the skipper and crew have to work together to keep the boat flatter.  The first thing to do is get your weight as far to windward as possible.  On most small boats, this means sitting on the windward rail and hiking out. For me, this is one of the most thrilling parts of sailing.

Many boats have hiking straps along the centerboard trunk, so you can hook your feet under them and lean way out to windward.  While you're hiking, hold onto the main or jib sheet to support some of your weight. The farther you lean out, the better leverage you will have with your weight, and the less your boat will heel.

Some boats use trapezes to get crew weight out even farther.  With a trapeze, the crew (and sometimes the skipper as well) wears a harness with a built-in hook. This hook is then connected to a wire that runs up to the mast, allowing the crew to put his or her feet on the rail and actually stand off the side of the boat, parallel to the water surface.  Trapezing is an exciting, and wet, part of sailing.

Moving your crew weight to windward, by itself, will not always keep your boat flat. When it's quite windy, you must use other methods to control heeling:

Pinching. When you start to heel too much, simply push the tiller to leeward a little so the boat heads up and the front part of the jib luffs. On a very windy day, it's not uncommon to sail upwind with 25% of the jib luffing to keep from heeling too much.

Ease the sails. Heeling is caused by wind pressure on the sails, so if you want to stop heeling, simply let your sails luff. Be sure to hold the mainsheet on windy days, and let it out whenever a puff makes you heel too much.

Depower your sails. When it's windy, a flat sail shape will cause less heeling than a full sail.

The best way to make heeling less scary is to make sure you and your crew are well-versed with capsize procedure, just in case. And anyone who is not a proficient swimmer should always wear a life jacket on the water.

Upwind "Feel"

As we said at the beginning of this chapter, sailing a boat upwind is an art that requires experience and a sensitivity to the way your helm feels. You will surely know it when the boat settles into the "groove." Things just feel right, and the boat almost sails itself.

It's possible to know a lot about sail trim, weight distribution and boat performance by tuning in to the feel of your hiking stick:

Windward (or weather) helm – A boat with windward helm will turn toward the wind when you let go of the tiller. It's good to have a little windward helm when sailing upwind, because this gives you a positive feel and helps the boat track to windward. Too much helm, however, means you will have to pull too hard on the tiller to keep the boat going straight. Reduce this helm by flattening the boat.

Neutral helm – When you have neutral helm, your boat will keep going straight when you let go of the tiller. This is ideal for downwind sailing, but it provides a mushy feel upwind.

Leeward helm – When you let go of the tiller, a boat with leeward helm will turn away from the wind. This is common in lighter air, but it's never desirable. You can get rid of leeward helm by making your boat heel more and trimming the sails in a bit.

Every crewmember should try to feel how the boat is going. This is much easier for the skipper, of course, because he is connected to the hull and the water through the tiller. That's why I suggest giving everyone on your boat a turn to steer. Besides, steering offers a great way to learn and have fun.