A Beginners Guide to Sailing

Want to learn to sail? That’s great—you have a whole future of adventure and discovery ahead. Sailors will tell you that there’s no substitute for the combined sensations of our sport: wind in your face, waves slapping the side of your boat, sunshine sparkling on the water. And all of this while you steer a course to your chosen destination.

learning to sail

You're never too old (or too young) to learn to sail. Photo: Neil Rabinowitz

Learning to sail is easiest on a boat less than 25 feet long. On larger boats, it takes longer to feel the effects of adjustments made to your course or sails. Everything you learn will translate to sailing a larger vessel, but when you pull in a line or move the helm on a small boat, you will immediately see and feel what happens as a result. That makes it easier to understand what’s happening, and why.

And if you've ever been on a sailboat, you already know that sailors have their own language. So the first step is to learn a few new words. Here’s a basic primer of sailing lingo, followed by general information on how we raise our sails, figure out where the wind is coming from, and control our speed and direction.

Learning to sail is easiest on a small boat

Learning to sail is easiest on a small boat, but all the skills transfer to a typical Caribbean charter boat like this one. Photo: John Burnham

Sailing Terms: Parts of a Sailboat

Watch our video, Sailing Terms:


Anything on the right side of the boat is “to starboard” or “on the starboard side.” Anything on the left side is “to port.” The front or pointy end is called the bow; the back is the stern. Any sailboat will have a few basic parts. The first is the hull, which is the actual body of the boat itself. Almost all hulls today are made of fiberglass; traditionally, boats were built of wood. Some specialty hulls are built of aluminum, carbon fiber, or steel.

parts of the boat hull mast boom

3 basic sailboat names: hull, mast, and boom.

The mast is the vertical pole or spar that supports the sails. Most sailboats will also have a shorter horizontal spar, which is called the boom. The joke is that this name comes from the sound it makes when it connects with your head, so make sure you stay out of its way once the sails are hoisted.

There are some free-standing masts, but most have a set of wires to support them; collectively, these wires are called the boat's standing rigging, because together they keep the mast standing up when the force of the wind fills the sails.

Read more: Sailing Terms: Sailboat Types, Rigs, Uses, and Definitions

Sailing Boat Basics: All About Sailing Lines

We control sails with ropes, which sailors call “lines.” There are many different kinds of lines on a sailboat, and each has its own name; the two most important types are halyards and sheets. A halyard pulls a sail up, which is called hoisting a sail. Each sail has its own designated halyard. Sheets control a sail’s trim once it’s hoisted. Each sail has its own designated sheet; some have a set of two—one on each side of the boat.

Single sail boat

This simple boat has one sail, which is controlled by one sheet—the line held by the young sailor.

There are many other lines that adjust the fine-tune trim of each sail, so you may also hear other line names used on board, including cunningham, vang, reef line, topping lift, foreguy, outhaul. We'll cover fine-tune trimming lines in an upcoming article.

sail names mainsail and jib

The mainsail is the primary sail. The jib sets in front of the mast.

Parts Of A Sail

There are several different types of sails, but most are triangular in shape. Each corner and each edge has a specific name. Some boats have only one sail, which is called the mainsail. The forward edge, the luff, goes up the mast, while the bottom edge, the foot, is attached to the boom. The aft edge, called the leech, flies free. On boats with two sails, the forward sail is called a jib. The jib luff attaches to the forestay, which is the piece of standing rigging in the bow, while the other two edges (foot and leech) typically fly free.

A third type of sail is called a spinnaker, and it’s usually lighter weight and more colorful than the plain-colored main and jib. A spinnaker is shaped like a balloon and attaches to the boat only at its corners; it is used for sailing downwind.

sail edges and corners

The head is the top of the sail, the clew is the aft corner, and the tack is the forward corner.

There are many other specialty sails for specific situations, so you may also hear words like: asymmetrical (often shortened to “A-sail”), kite, jib-top, mizzen, reacher, staysail. No matter what kind of sail it is, the three corners all have the same name. The head is the top of the sail, the clew is the aft corner, and the tack is the forward corner.

Sails are sized to fit on a specific boat in a particular way. Naming the corners and edges makes it easier to attach them correctly each time. On bigger boats, the corners may even be labeled by the sailmaker to reduce the chances of hooking up a sail incorrectly.

Hoisting the jib

Hoisting the jib on a 1938 Herreshoff Marlin.

Hoist Your Sails

Before we can go sailing, we need to pull up the sails so they can fill with wind. Here's a short video showing how this is done:

First, we find the right halyard. Typically there is one for each sail; the main halyard runs down the aft or backside of the mast, while the jib halyard runs down the forward side.

The first time you hoist your sails, consider doing so on land (as we do in our Learn to Hoist video) or while tied to a dock or mooring, when the wind is very light. That way you won’t have the added variables of moving across the water, while you are learning how your halyards attach and where they are fastened off after hoisting.

Each sail has its own halyard, and it’s important to use the correct one. If we were to hoist the mainsail with the jib halyard, the sail would get twisted around the mast. That’s why it’s important to look up the mast before attaching the halyard to the sail, to make sure the sail will go up smoothly.

The way a specific halyard attaches varies widely from one boat to another, but always be sure that the attachment is secure.

One last thing: Before pulling on the other end of the halyard, always check again that it runs straight to the top of the mast: no twists, turns, or unexpected wraps. Pulling on a halyard that’s looped around something else can lead to expensive damage of either sails or rigging—or both.

Depending on the size of your boat, it may only take a few pulls to get the sail up all the way—or you may need a winch and some serious muscle for the final tensioning. Either way, once the sail is hoisted completely, tie off the halyard to keep it from falling down again. There should be a nearby cleat or other means to tie it off securely.

Next, we hoist the jib. Again, check that you’re using the right halyard, attach it securely, look up before you hoist, and tie it off so it doesn’t fall down again. Once each halyard is secure, coil up the extra line and tuck it out of the way so it doesn’t get tangled. That way it can be freed easily when you need to drop your sails again.

How Does The Wind Affect Sailing?

Sailors know almost instinctively where the wind is coming from because it tells them a lot about what kind of day they will have on the water. When we talk about wind direction, though, there are two very different levels of detail we may be discussing: the absolute direction (“the wind is from the northwest today”); or the relative direction of the wind to where our boat is pointing (“we are on a close reach right now”). Both are important, just as seeing the forest and not forgetting about the trees is important. Absolute direction is part of a bigger picture weather discussion, while the relative angle of the wind to our boat changes every time we adjust our course.

In either case, we use the same clues to figure out the wind direction. The best indicator is a nearby flag—or anything that is out in the open, fixed at one edge, and flying free at the other. Flags blow downwind, so if you point from the loose end back to its attachment point, you’ll be pointing into the wind.

Flags on the Oliver Hazard Perry

Flags like these flying from the tall ship Oliver Hazard Perry are one of the best ways to tell where the wind is coming from.

Watch any flag carefully for a minute or two, and you’ll notice that its direction varies quite a bit over time. And depending on what’s upwind of it, a flag might never show the true wind direction correctly. So it’s important to look at a flag that’s unobstructed by buildings, trees, or anything else that might create a wind shadow.

Because we can't count on having a flag nearby, many boats have telltales tied to their rigging. This is just a fancy word for a piece of colorful yarn that will show us the wind direction no matter how far from the land we go.

Now that we know how to figure out where the wind is coming from, we can also determine the “windward” side of the boat—the side closest to the wind. The opposite side is the “leeward” side. These terms will be important when we learn how to trim our sails.

Points Of Sail

The direction of our boat in relation to the wind changes every time we alter course, and each of those directions has a name; together, they are called the “points of sail”. If we point our boat straight into the wind, the sails will flap or “luff.” The sail becomes a flag, showing the direction of the wind rather than filling with it, which is why a boat can’t sail straight into the wind.

head to wind: boats can't sail directly upwind.

If a boat points into the wind, the sails will luff like a flag.

As the bow turns away from the wind, the sails will fill, and the boat will begin sailing on what's called a close-hauled course—as close to sailing directly into the wind as possible. Exactly how close a boat can sail to the wind depends on the boat's design, wind strength, and sail shape and trim. The boat in the diagram below is on starboard tack because the wind is coming over the starboard, or right hand, side of the boat. This is also called the windward side.

Close hauled on starboard tack

Close hauled on starboard tack means the boat is sailing as close to the wind as possible.

Tacking passes the bow of the boat quickly through the wind and fills the sails on the opposite side. Alternating tacks between sailing close-hauled on starboard and sailing close-hauled on port is called beating to windward or sailing upwind, and it’s the only way to make progress directly toward where the wind is coming from. The boat's course will adjust as the wind shifts, in order to sail as close to the desired course as possible.

close hauled port tack

Close hauled on port tack: the wind is coming over the port side of the boat.

As soon as we turn the bow farther away from the wind than close-hauled, the boat is on a close reach. In the video, we say a close reach is at 45 degrees to the wind, but actually the exact angle can vary anywhere from 45-70 degrees depending on the boat. The key distinction is that we are now sailing in a specific direction, rather than constantly adjusting our course to any changing angle of the wind.

points of sail port tack close reach

The exact angle of a close reach varies, but we are no longer trying to sail as close to the wind as possible.

When the bow is pointing at 90 degrees to the wind, that angle is called a beam reach.


When the wind is on the "beam" of the boat, we are on a beam reach.

At 120 degrees, we're on a broad reach.


With the wind at 120 degrees, we're on a broad reach.

Sailing directly downwind is called running, or running before the wind.


Once the wind is directly astern, we are running before the wind.

When the wind passes across the stern of the boat, we jibe, and the sails switch to the other side of the boat. As the angle of the wind changes we need to adjust or “trim” our sails. A sail perfectly trimmed for a broad reach will luff when on a close reach. When sails luff, they stop propelling the boat forward. Here are some basic rules to help you trim your sails correctly.

Sail Trim

Sail trim is very important to sailors, especially racing sailors. Entire books have been written about the fine points of sail trim, because even a tiny adjustment can decide who wins a championship sailboat race. Fortunately, fine-tuned trim isn’t necessary to enjoy an afternoon sail, and the basics are pretty simple to understand.

Jolie brise under sail

Basic sail trim is all you need for an enjoyable afternoon sail on Jolie Brise, a boat that was built in 1913. Photo courtesy of Dauntsey’s School/Jolie Brise.

As a general rule, we pull in the sails until they stop luffing. Exactly how much trim is needed to make that happen will depend on our point of sail. The farther the bow points away from the wind, the more we can ease our sheets without the sail luffing. So sailing close-hauled, we'll need to pull in the sheet as much as possible. Running before the wind, we can let the sail out as far as it will go. If we turn toward the wind or head up without trimming in the sail, it will begin to luff and the boat will slow down. If we turn away from the wind or bear off, we can ease the sail out more without it bluffing.

The three rules of basic sail trim are:

  1. Trim the sail in until it stops luffing.

  2. Pull the sails in as you head up or sail closer to the wind.

  3. Ease the sails out as you bear off or turn away from the wind.

Trimming in the mainsail is easy: you pull on the mainsheet, and the boom and sail move closer to the centerline of the boat.

The jib will usually have two sheets—one that runs down each side of the boat. To trim the jib, pull in the sheet farthest away from the wind—the leeward sheet. The jib will fill to leeward of the mainsail. If the clew, or aft corner, of the jib appears to windward of the mainsail or mast, you’re pulling on the wrong line, which will act like a brake and also make the boat want to bear offaway from the wind. Ease it out and pull in the leeward jibsheet instead; that will help you move forward and allow you to sail your desired course.

jib sheets on a Snipe

The two green lines attached to the jib clew are the port and starboard jib sheets. This sailor has correctly trimmed in the sail on the leeward side of the boat; the windward sheet hangs loose on its way around the front of the mast, ready to be pulled in when the boat changes tacks.

To see how trimming sails work with your own eyes, check out our