Sometimes You Have to Sail Upwind: Perfecting the Tack

Perfecting tacking on your cruising boat can go a long way to more efficient sailing, not to mention an easier ride for your passengers. Our resident expert Dave Flynn details what you need to know to effectively sail upwind.

While it would be wonderful to live in a perfect world where we never have to go upwind, reality usually rears its ugly head at the least opportune times. Just as you’re getting ready to put the finishing touches on a pleasant week-long cruise, you’ll suddenly face a nasty 10-mile passage straight upwind with a deadline to get back to work.

Unfortunately, the majority of cruising boats are relatively compromised when it comes to upwind performance: shallow draft, wide beam, awkward sail controls, not to mention that you’re carrying your house around with you. All of this works against the act of making time to weather. When you find yourself in this situation, keep these things in mind.

Don’t Force It

Yes, I know you want to get there, but you can’t just point your boat where you want to go. You have to balance off speed and pointing – based on the wind velocity and sea state – to strike the best compromise. Remember, always speed first before you try to sheet in harder and force the boat to point. If you jam things in and pinch, you’ll only go sideways.

The next trick is a tip from Racing Strategy 101: sail the long tack first, and hope for a wind shift that will make it easier to get there. It’s relatively unusual for a beat to be perfectly square (equal time on both tacks). Figure out which tack is closer to where you want to go and sail it first.

Finally, recognize that, since you are not going to force it, you will ultimately have to tack multiple times. Good technique can go a long way towards making the whole exercise less painful.

There are two keys to a good tack:

  1. Preparation
  2. Technique and Timing


A good tack starts with preparation. Make sure the old sheet is ready to run and that the person doing the release is ready before you start the turn. Check for potential hang-ups on mast winches, dinghies, drink holders, etc.

A countdown helps everyone with the timing: “Three, two, one, turning the boat.” Notice I didn’t use the term “hard a lee.” This term should be abolished. The fact is you don’t want to turn hard, but smooth and steady. The rudder is a brake. Turning it hard puts the brakes on. The goal should be to turn as slowly as possible without losing too much speed. Certainly, if you get stuck in irons you have turned too slow, but a good rule of thumb is to not slow down more than half your upwind speed entering the tack.

Each turn will be a little different depending on wind speed and sea state. If the waves are big or the wind is light, you’ll need to turn faster. In moderate conditions and smooth water, you can drag things out.

The beauty of a good turn is that right in the middle you are coasting exactly upwind, straight towards where you want to go. The other benefit of a smooth, consistent turn is that the trimmer – who has to pull the sail in on the new side – will love you. If you turn too fast or vary the rate, there’s a high probability that you’ll over rotate. The headsail will suddenly snap through the foretriangle and the sheet trimmer will not have time to pull it in before it fills well away from the boat. Much grinding ensues.

Be careful not to turn too far. The sweet spot is at the new close-hauled angle. Even if the sail is still luffing, that’s okay. It will give your trimmer a chance to pull it in. In racing, it is called “the trimmers luff.”

Technique and Timing

The other key to a good tack is, oddly enough, the release (not pulling the sail in on the new side).

As the boat heads up slowly into the wind – as the sail luffs nearly half way back along its length and before it hits the spreader – spin all the wraps off the winch and release completely. Make sure the sheet runs, even pulling additional sheet out from in front of any turning blocks that may be in the way.

Never back against a spreader! Spreader abuse is one of the principal ways to ruin a perfectly good sail.

On the new side, take your time. I know it’s your big moment, but your helms person is going to make it easy. Casually take up the slack as the sail starts to come around. Don’t pull hard or you’ll pull the sail back into the rigging and make it harder for it to get across.

There’s a critical moment when the clew passes the leeward shrouds: that’s when you pull like crazy. This is when you have lots of slack, but no load because the sail hasn’t filled. It’s never going to be as easy: stand up, stay well away from the winch, brace yourself (sitting on the cockpit seat completely incapacitates you), and pull from a position of strength using your body weight.

Remember, this is a sport! It rewards technique and timing. Don’t have too many turns on the winch, and don’t try to pull through the self-tailor (two or three is usually plenty, depending on the size the of boat and wind strength). Add wraps and slip into the self-tailor at the very end, when all the easy slack is out and you are ready to grind.

To grind, try straddling the coaming with your weight over the winch so you can use your body (of course you can just press the button if you have power winches). Always look up at the sail relative to the spreader so you know when you are the same distance off the spreader that you were on the other tack. (By the way, this same basic technique – stand up, assume an athletic balanced position, and look up towards the spreader to watch what you are pulling – applies to the release as well.)

A note for those of you on larger cruising boats with classic cutter rigs, where the inner forestay is always in place: you can force your big headsail through the gap between inner and outer forestays, but I wouldn’t recommend it. You can leave the staysail sheeted in and try to slide the big sail around the little one, but it’s not fast, and it’s tough on both sails (you’ll be replacing your UV covers on a regular basis).

Proper technique involves rolling the sail in most of way (at least until the clew passes the inner forestay) before releasing the old sheet completely and starting to haul in on the new side. It takes a little coordination between the rate of turn, the person on the sheet, and the crew on the furling line (which is hopefully operated with a button). With practice, you can get them down almost as smoothly (though a little slower) than on a boat where you don’t have to contend with an inner forestay.

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