How to Sail [Complete Beginner Guide]

Sinbad the Sailor, Pirates of the Caribbean and Maiden trip are some of the popular films which have stoked the embers of sailing in many fans around the world.

Sinbad was a hero who went to faraway places to fight monsters and evil adversaries.

Jack Sparrow, in Pirates of the Caribbean, is a hero who hides his cunning nature behind his bumbling exterior, eliciting laughter and admiration in equal measures.

Maiden trip is about 14-year-old Laura Dekker who sets out to document a two-year voyage and set the record of being the youngest sailor to ever sail around the world.

Whichever character you subscribe to and admire, there is a basic attraction to live up to the adventures depicted in these movies.

However, before you go out and manifest your marine-conquering dreams, you must face reality.

There’s no way you can set sail on your adventures without learning how to sail

As with all other endeavors, you must prepare for the uncertainties at sea by getting top-notch theoretical and hands-on instructions from an accredited school on how to sail a boat.

Before you go out and search for a sailing school or club, get to know some of the jargon that will be used in the lessons so you are not left behind.

If you'd like to know more about sailing specific boats, we have a sailing a catamaran guide you can check out. Once you learn how to sail. there are a number of different types of sailboats you can operate.

When you're more experienced at sailing, you can attempt to sail across the Atlantic (although we wouldn't recommend it for newbies) or you might end up sailing against the wind

Either way, it can be a lot of fun!

The basic nautical terms used in sailing


Here is a list of the names and terms used in the sailing world:

1)     The Sails – Sailing crafts have two basic sails:


a)     The Jib – The small sail located at the front of the mast.

b)     The Mainsail – The large sail located behind the mast.


2)     The steering mechanism – There are two main parts:


a)     The Rudder – The fin-like board that projects from the center-line of the boat and used to swing the boat to the left or right.

b)     The Tiller – The horizontal bar which operates the rudder. Pushing the tiller to one side makes the rudder shift to the opposite side. Extensions are added in some boats and dinghies allowing operation of the rudder from a further distance.


3)     The Hull – The main body of the boat; you and everything else on the boat are carried upon the hull. It is made of strong material to bear the stress and weight that is exerted on it by luggage, persons and the forces of the water.


4)     Aft – Refers to the back end of the boater ship. The term “Stern” also refers to the back of the boat.


5)     Bow – Refers to the front of the vessel. The term “Fore” also refers to the front of the boat.


6)     Port – Refers to the left side of the boat with respect to the bow of the boat or ship; remember, it is a direction based on the bow of the boat. When out in open waters, you may mistake the left side when the boat is moving backwards and you are facing aft. An easy tip on recalling this is that both Port and Left have 4 letters each.


7)     Starboard – Refers to the right side of the boat when facing the bow. It is opposite the port side. Easy to recall, right…? Or should I say easy to recall, starboard?


8)     The Beam – The widest or broadest part of the boat.


9)     The Boom – The horizontal beam that extends from the lower part of the mast. It is swung in the direction of the wind in order to harvest the wind and make the boat move fore or aft. Remember what fore and aft mean? Kudos, you are getting the hang on these terms quite well.


10)  Telltales – Small strings attached to the boat sides which indicate the direction of the wind. You don’t have to stick a finger in your mouth and hold it up to tell wind direction.


11)  The Keel – Acts like a small anchor and stabilizes the boat in an upward position. This is so the boat does not ‘keel’ over in the water. It is also used to regulate the speed of the boat. When its pulled upwards, the boat runs faster, a position known at the running position.


12)  Windward – Refers to the direction that the wind is coming from. Since sailboats move with the wind, it is one of the important sail boat operation terms that you should know.


13)  Leeward – Refers to the direction that the wind is blowing towards.


14)  Tacking – A maneuver involving moving the boom from one side of the boat to the other so the bow/fore of the vessel turns through the wind.


15)  Jibing – A maneuver that turns the aft/stern of the boat through the wind, by changing the wind from one side of the vessel to the other. However, this is a move rarely used because it turns the boat directly into the wind.

You can read our full list of sailing terms to get a more in depth understanding when starting out. l


These are the basic terms you will encounter when you are learning how to sail. Keep running through them and soon, exclamations like “Let go aft!” and “All hands on deck!” will be naturally rolling off your tongue.

Now you have some theoretical knowledge of the parts of the boat and how these work together in steering the boat and navigating through open seas.

However, you are not yet ready to take the helm of any boat, especially in open waters until you get hands-on training from a school, club or local boating community.

Having practical lessons from seasoned instructors prepares you to safely operate the boat, irrespective of any situation that you may encounter, so you can’t skip this part of your training.

What you will learn during practical lessons on how to sail a boat

1) Basics lessons in learning how to sail

a)     Rigging a boat

Before you step into a boat and take it out, even in calm waters near your anchorage point, you need to know how to rigid first.

In these lessons, you go through the steps involved in putting up the sails and checking that all parts are in working order. There is a process that you must use when inspecting the boat, before you set sail, and you will cover these when learning how to rid a boat.

b)     Basic maneuvering of a boat

In this part, you go through the steps involved in keeping the boat in a steady directions and also what you must do when steering the boat.

i)       You must know how to set the boat to sail in a certain direction

ii)      You must know how to keep the boat steady in the direction that you have chosen

iii)    You must know how to change the course of the boat through steering with the helm and also steering with the sails.


c)      How to dock or anchor the boat

You now know how to maneuver the boat and have taken it out on a trial run a few meters out in the water.

But how do you get back and dock the boat?

This is an important lesson that teaches you how to approach the dock, get off the boat and anchor it safely.


d)     How to deal with emergencies

The most life-threatening situation when you are sailing is when the boat capsizes. Small boats are prone to tipping over in strong winds, especially when you have fully deployed the sails.

This is a critical lesson that teaches you how to get up on top of the capsized boat, or how to return it into the upright position if the boat is small enough or if you are sailing with other people.

You will also get handy instructions on how to deal with smaller emergencies.

If a fire breaks out on your boat, you'll need to know all the emergency sailing protocols to ensure you and your passengers are safe.

These are the most basic practical lessons that you will go through when learning how to sail a catamaran and other small boats.

2)  Advanced lessons in learning how to sail

a)     Running the boat

When the wind is coming from astern, the boat is said to be “Running”.

The mainsail of the boat has to be as close as possible to a 90 degree angle with respect to the wind when it is running.

The main-sheet, controlling the angle of the mainsail, should be slacked off so it assumes an angle close to 90 degrees.

There is no lateral push from the wind when the boat is in this position, since the bow points straight into the wind.

Without any lateral thrust, the risk of the boat keeling over, or capsizing is greatly reduced. It is therefore safe to raise the keel so there is less drag making the boat move faster through the water. Perhaps this is why the term “running” was coined to describe this position.

Be careful when you are in the running position; in this case, the wind is blowing from the aft direction (astern),and doesn’t have a steadying effect on the sails, making the boat prone to rolling.

To be on the safe side, keep the keel partially submerged to avoid rolling or yawing (the side-to-side movement of the boat).

b)     Reaching the boat

When the wind is blowing from the beam, the boat is said to be “Reaching”.

The mainsail and the jib must be pulled close together and the angle of the wind may vary across a wide arc.

Close-reach – this is when the wind is coming from the front of the beam.

Broad-reach – this is when the wind is blowing from further aft of the beam.

The mainsail and jib are in a closer position during close reach than broad reach. One cannot fully know when the position of the mainsail and jib are close enough. The best way to ascertain this is to push the lull of the sails (the position closest to the mast) and make sure it has a soft feel.

Reaching will bring out the adrenaline in your body since it is the fastest, safest and easiest steering position in which to sail.

c)      Beating the boat

When the wind is blowing from the bow, the boat is said to be “beating”.

Practically, a boat will never sail directly into the wind. However, in the beating position, the wind simply comes from the front of the boat in a diagonal direction.

The sails are pulled in closer than the reaching position. You must keep an eye on the sails and ensure that they have not been pulled in too close.

Should the boat sail directly into the wind, the sails will not get filled, and the boat will slow down and eventually come to a stop. You will also lose control of the boat since the rudder will not work properly during slow speeds or when the boat eventually stops.

It takes a lot of practice to perform the beating maneuver. Should the wind change direction, or suddenly gusts up, the boat may heel and even capsize.

Do not perform this maneuver until you have enough practical knowledge on how to go about it.

At this point, you have the basics of how to handle a sailing boat, and you may now go and hone your skills in the open waters.

d) Night Sailing

Once you get into the more advanced sailing lessons, you'll also be trained on how to safely operate a vessel at night. These lessons can be very exciting and you will be taught the extra precautions to take when onboard in the dark. For more information, you can check out our boating at night article to help.

e) Sailing with crew

As you get to the advanced sailing lessons, you'll also learn how to operate a sailboat with crew. Generally speaking, larger boats will require the assistance of crew which your instructor should fill you in on. However, you should also ask the sailing instructor for lessons on how to sail with babies onboard (if of course you have children) and how to boat with dogs, if you plan on bringing your pet onboard. Most new sailors forget to learn safety precautions for doing this.

Join a sailing club or local sailing community

It is advisable to join a sailing club or local sailing community so you are always accounted for when you go out sailing. There are lot's of places where you can learn how to sail, example.....New York Clubs

After you learn how to sail, sailing clubs offer you the best and safest way to hone your skills. You take your boat out in the company of other boats in close proximity. This way, should anything happen, you have experienced sailors ready to come to your assistance.

how to sail

The same applies for local sailing communities, where you go out with your friends and neighbors for a day of sailing in the open seas.

Go through your local sailing directory and join a club or community that appeals to you.

When you get some more experience with sailing, you can eventually use the autopilot features on a sailboat, which can come in quite handy on long distance trips.

Sailing Qualifications

Depending on where you are in the world, you will need different qualifications in order to operate a sailboat. Typically, the instructor where you get lessons will inform you on what is required. If you'd like. you can check out our sailing qualification requirements article for more information.

You can learn the basics of sailing on beginner friendly sailing dinghies to get started and then work your way up to more advanced options when you can more experience.


It is now safe to imagine yourself standing tall at the helm of a catamaran, watching the waters part in front of its unrelenting hull, powered by the full wind filling up her sails.

The wind blowing in your face; the never-ending expanse of deep blue ocean waters, eyes constantly scanning the horizon for a sign of land; perhaps a deserted island you can name after yourself.

The excitement of sailing around the world is one that few can resist.

However, every beginner must go through in-depth training in order to safely sail on open waters. There are several dangers lurking out there and you must be equipped to handle them should they arise. It's best to plan a sailing trip in advance to ensure you are prepared for every outcome.

Otherwise, go out and live your adventure after careful instruction on how to sail a boat, and have the most fun-time you have ever had.