Knowing how to sail upwind efficiently is what separates a sailor who's just holding on from one who's actually making progress.
Most people point the bow toward the wind, trim in tight, and wonder why the boat feels like it's going nowhere.
The problem usually comes down to two things: pointing too high or sailing too low. Both drain your speed in different ways.
This post breaks down the trade-offs between pinching and footing and shows you how to use telltales and sail trim to find the groove.
When you sail close-hauled (as close to the wind as possible), you're trying to reach a directly upwind point.
No sailboat can point straight into the wind, so you zigzag in a series of tacks, switching the bow through the wind direction to gain ground.
The question isn't whether you can get there. It's how quickly you can get there.
That brings us to the single most important number in upwind performance, which is velocity made good, or VGM.
VGM tells you how much progress you're actually making toward your upwind target. That's different from boat speed, which only tells you how quickly you're moving through the water.
Here's the problem:
The sweet spot between these two is what sailors call "the groove." It's where your angle and your speed work together to get you to windward as quickly as possible.
That groove is one of the most satisfying things you'll learn to find on the water.
Every helmsman faces this choice on every beat. Here's what each mistake looks like and when it actually makes sense to use it.
Most sailors instinctively pinch. It feels like you're winning since you're pointing closer to your target.
The numbers say otherwise. You're losing VMG with every degree you overpoint.
Telltales are yarn strips attached to your jib (the front sail). They show you how air is flowing over the sail at that moment, which tells you whether you're in the groove or not.
Look at the pair about a foot back from the luff (the front edge of the jib).
Here's what they mean:
The concept is simple enough. What makes it tricky is reading them while gusts, waves, and wind shifts keep changing conditions around you.
Staying in the groove isn't just about where you point the bow. How you set up your sails does half the work.
Here are the adjustments worth paying attention to.
Reducing the curve in your sails when the breeze picks up cuts heel (how much the boat leans). Less heel means less drag on the rudder and better speed to windward.
Too much heel loads up the rudder, slows the boat, and makes it harder for the helmsman to hold the groove.
If you learned to sail on a dinghy with a tiller in your hand, stepping onto a 40-foot monohull or catamaran will feel very different.
Here's why.
A tiller vibrates and pulls the moment you lose flow. Wheel steering connects through cables or hydraulics, so that feedback is muted.
You won't feel the stall as quickly, which means your eyes have to do the work instead.
A heavy cruising yacht takes a long time to speed up again once it slows down. If you pinch and lose your boat speed, getting that "heavy train" rolling again takes patience.
Keeping your speed up matters more on a larger boat than squeezing out one more degree of pointing.
Practicing on full-size cruising yachts creates better habits for this reason. You learn to read what you see, manage momentum, and trim the sails for the boats you'll actually charter.
Even perfect trim and flawless telltale reading won't help much if you ignore wind shifts.
Here's the rule experienced sailors swear by: sail the lifts, tack on the headers.
A lift occurs when the wind shifts in your favour, allowing you to point closer to your target without changing course.
In contrast, a header pushes the bow away from your target and forces you to bear off or tack sooner than planned.
When you notice a header (the wind direction turns toward your bow), tack, and you'll now be on a lift on the other side, gaining ground quicker.
When you're on a lift and getting close to the edge of your course, that's the time to go for it. Ease the backstay, let the boat accelerate, and gain ground on another boat sailing to leeward.
Paying attention to these shifts is what turns a long, grinding beat into a series of well-timed moves that get you to windward quicker.
Out on the water, a lift feels like a quiet advantage. You’re sailing along, and suddenly the boat can point higher without changing trim or touching the helm.
The wind shifts slightly in your favour, and you gain ground simply by holding course.
A header feels different. The bow starts falling away from your target. You either bear off and lose ground or tack sooner than planned.
The Sailing Virgins Intermediate Course puts you on a 7-day liveaboard adventure where you earn your ASA 104 Bareboat Cruising certification.
You'll practice tacks, trim, and upwind sailing daily in conditions that change every hour, sailing through the BVI, Croatia, or Greece. By the end of the week, you’ll learn how to sail upwind efficiently.
Check out the Intermediate Course and spend a week turning theory into instinct.