Is Sailing Difficult To Learn? An Introduction For Beginners

One of my favorite quotes on sailing comes from John F. Kennedy: “We are tied to the ocean. And when we go back to the sea, whether it is to sail or to watch – we are going back from whence we came.” If you feel tied to the ocean and hear a calling to sail, there is nothing stopping you from learning this rewarding and freeing pastime.

Is Sailing Difficult to Learn? The overall verdict is that you can learn to sail in the matter of a few hours or an afternoon. You may get yourself from point A to point B, but to be an expert sailor, it will involve a lifetime of learning and experience. Even lifelong sailors say they are still learning.

I’ve sailed nearly a dozen times, and I can tell you from experience that sailing is not difficult, as long as you are working with an efficient crew. To sail on your own would be something else entirely, but obviously not impossible. This guide will be your go-to source on every question that is asked most frequently regarding the sport, as well as the first steps to take in fulfilling your dream of sailing around the world! Let’s take that first step now!

Is Sailing Difficult to Learn?

To give you an answer from a real expert that has been sailing for more than 40 years, Liam Crowleigh, describes it as, “Learning to sail is both very easy and at the same time very difficult.”

It is both. So you’ll have to get over the mentality of believing that it’s one or the other.

The logistics of sailing are quite easy to learn. You can learn the basic movements and techniques on your first day out in a sailboat.

The captain allowed me to steer the boat for four to five hours when I was only 7 years old. I am not the only story like this. There are countless tales of people sailing a boat when they were 12, 13, even since they were 5 years old!

I use this example to suggest that getting started is not difficult. However, there is certainly risk and you will always be significantly safer when sailing with an experienced crew to guide and support you. Sailing alone, even as an expert, can be dangerous because if you’re knocked overboard and drown, no one will be there to assist you or save your life.

Another way to think of the difficulty-level of sailing is to think about driving your car. When you learned to drive, you can get a handle for what movement causes what reaction, which pedal is stop, which pedal is go – all in about 30 minutes to an hour. But you may spend your entire life becoming a better and better driver through experience.

All of this practical application and time spent growing your skill will gather up into a lifetime of education.

How Long Does Sailing Take to Learn?

The answer is an afternoon and a lifetime.

Some describe it as “about the same amount of time as learning to ride a bike,” while other say that the difficult and long part is actually learning to sail well.

The first place to start will be enrolling in a training course, such as the ASA (American Sailing Association) Certification Training. You can use this link to start your online training or find the nearest sailing school to your local zip code.

The duration of an ASA Sailing course will usually take 6 days, which are often broken up into three separate weekends.

Sometimes you will be required to pass an initial examination that proves you can do basic docking and undocking procedures before they allow you to take a charter sailboat out on the water.

The best way to learn is through spending time on the boat and sitting back to observe the first time or two. Don’t be in a rush to get at the helm of the boat as you have your whole lifetime to lead your crew.

How Much Does It Cost?

Some of the different rates and price-ranges you can expect for ASA trainings include:

  • Basic 101 training – Between $250-$350 for two 7-hour days
  • Emergency Medicine Class when Offshore – $900-$1200 for a three-day course and certification
  • ASA Home Study Coastal Navigation Course – $75-$150 plus $30-$50 testing fee

You can usually expect to spend at least $1,000 getting started realistically and anywhere up to $10,000-$50,000 on average if you want to own your own sailboat.

It can be free if you want to just go out with your buddies on a sailboat. But if you plan to captain the boat or own your own, you will need a license and, therefore, not be allowed to sail alone without one sans certification.

You can read more course variations and price-differences based on ASA locations around the country here.

A way to make it more affordable is if you can self-teach and study from home. This may allow you to test out of certain courses, meaning if you pass them, you may only pay up to $50 for a testing fee.

Experience will be your best asset, and taking a sailing course is truly one of the best and safest ways to learn.

One final tip on cost is a forum on sailing difficulty review that I appreciated from a sailor who’s been enamored with the sport for the last 20 years. He offers advice on owning a boat with your friends to make it more affordable 8saying:

“If you want to buy a boat on the cheap, think about starting a partnership with other friends, family, or sailors. I have been sailing a 30-foot sailboat on the SF Bay for the last 17 years for $3 per day. We each pay $100 per month with 6 partners. That covers most of our costs. Sailing is an amazing sport that you can do your entire life.”

Do You Need a License to Sail?

Just to be clear on a topic we grazed over in the last section, yes, if you want to captain your own shit, you will need a USCG Captains License. There are different licenses for wanting to captain a ship of 6 passengers (an OUPV/Six-Pack License) and captaining a ship of 100 passengers.

This means you may need to understand your intention regarding sailing and be certain you actually enjoy it before aiming for the larger crewed certifications. It is recommended to start with a smaller crew then work your way up.

Here is more information on the different types of sailing licenses available.

I would also recommend you to take a look at the American Boater Association Laws and Requirements to be better equipped with the knowledge of what the legal requirements will be for where you live.

The license may take between 25-50 hours of credit hours, with further time spent studying beforehand and a lifetime spent studying afterwards.

A remark from a popular boating school states that “We have had students finish in as little as three days, three weeks, three months, or up to a year.”

Take the pace that fits into your lifestyle, and don’t rush it. You will be much more likely to finish it this way and stick with it rather than spreading yourself too thin.

Tips Before Going Out on The Water

Some things you need to do before beginning your sailing or going out on the water include:

  • Understand PFD and Lifejacket Regulations – The Laws State by State
  • Start with a smaller boat while still learning. This will cause you to feel the tipping sensation more and be more susceptible to countering that imbalance. This will lead to you feeling even more prepared and competent on a large sailboat.
  • Always check the weather and don’t go out in high winds or high chances of rain/storms
  • Take a course, as recommended above and as required by law if you want to captain.
  • Find a crew so that you don’t have to sail alone and increase your risk of injury/death. You can also hire a crew from most boating companies or recruit skippers in your area that literally want to learn the ropes with you.
  • Know that you can’t sail upwind. If you don’t understand this, you’re not ready to go out independently.
  • Confirm there is a paddle onboard incase a sail gets damaged.
  • Be sure you are appropriately dressed for the weather. Keep in mind you will be on the water where it is colder, and in the wind, so budget for it feeling about 20-degrees colder than it is.
  • Always be certain that you a first-aid kit handy onboard.
  • Always have a knife of some kind onboard.
  • Always check your safety equipment, inspect the ship, check all lines, confirm that the sails don’t have any holes, and so on – before heading out to sea.
  • Always have a game-plan for heading out and docking back to shore. You will need to know this beforehand to avoid grinding your rudder into the shore or damaging your daggerboard if you’re beaching your sailboat.

It will always be better to learn visually and stick with a real expert until you are confident as a seaman. You will also need to know the popular terms your instructor will be using before actually going on the boat. It may not be necessary for your first lesson, but it will certainly give you a leg up.

Learning the Lingo

There are many words you’ll need to know before going out, the most important of which being:

  • Port – if you’re looking at the front of a sailboat, this will be the left side of the boat.
  • Starboard – if you’re looking at the front of a sailboat, this will be the right side of the boat.

Pro Tip: When I worked for a cruising travel agency, we were constantly using Port and Starboard. The best tip I heard for keeping these straight is that “port” has 4-letters just like left. If you can remember that Port is left, then Starboard will be easier to remember as right.

  • Bow/Stern – the back of the boat.
  • Heeling – when the boat is leaning or tipping into the water
  • Jibe – a way of expressing a directional change. Sometimes interchangeable with Tack.
  • Windward – the side of the boat which is closest or against the wind. If you’re heeling over or capsizing, this is the side which is highest.
  • Leeward – the low side in the preceding scenario.
  • Lines – the ropes.
  • Helm – the big wheel you steer with.

You can reference ASA’s basic terms as well as a more comprehensive guide such as this one on all sailing terms.

Learning the Knots

Knots are an integral part of sailing and such a visual component to the process that I couldn’t possibly explain with words alone.

Here is a link to the 10 Essential Knots as a Sailor with photographs and subsequent explanations.

Racing is a wonderful way to gain experience in tying knots. This is something you can practice at home before getting out to the sea.

You need to be able to do these knots with your eyes closed before you can be certain of your sailing dexterity. Knots and lingo are two fundamental parts of sailing, outside of proper hands-on and physical experience.

Tips Once You Are Out on The Water

Some advice that should be your guide when you’re out on the water (hopefully with an instructor for the first many hours at sea) includes:

  • Always pick a day with favorable weather conditions. You want some winds to be able to move at all, but not too many that you’ll be capsized by the time you reach deeper waters.
  • Always go with an expert for your first 20-100 hours. An ASA instructor is recommended.
  • Always watch out for the boom – this is the large bar at the foot of the ship near the main sail. It moves back and forth and is the bar you’ve seen knock so many movie characters into the water. Don’t be this guy.
  • If you are ever going out alone (down the line when you’re more of an expert), be sure someone knows where you are going and your expected time of arrival back home. If you go missing, you’ll want someone to know your whereabouts.

Other Investments You May Need to Make

You may need some equipment if you’re serious about having your own boat or having the freedom to sail whenever you please without rentals.

You will need to dress for the occasion and prepare like you’re a boy-scout, and it’s your motto!

Some investments you may need to make beforehand to be fully prepared for a life at sea may include but are not limited to:

  • Heavy-Duty Gloves – you will need rubber-coated or very thick gloves to avoid rope-burn and feeling immense pain. Some sailors prefer fingerless gloves are those that leave at least their fingertips exposed, but this is a matter of preference.
  • Good shoes that don’t slip or water-resistant footwear
  • A Logbook – to keep track of the courses you’ve taken and note your experience and highlights. The creator of this logbook comes from the man that taught Charles Lindbergh to navigate, so it is a very popular logbook for beginner sailors.
  • A Windbreaker Jacket
  • Sunscreen
  • A Lifejacket or PFD – aim for one that is approved by the Coast Guard, or at the least is reputable with solid reviews.
  • Dry Bags – for sailing or any water sport to keep your valuables safe and your money dry!
  • Polarized sunglasses – these will remove any glares from the sun and make it easier for you to see your surroundings, read the waves, and therefore read the wind. All of which are imperative to your sailing success. Invest in good shades.

You may also need to bring:

  • Original and/or copy of your passport; don’t keep both in the same place in case one storage area gets wet, backpack stolen, etc. so you still have backup safe.
  • Towels
  • First aid kit (unless the boat already has one)

Is Sailing Dangerous?

Sailing isn’t dangerous, but one can’t necessarily say that it’s completely safe either. People occasionally drown, deaths happen, and most of the injuries/fatalities can be avoided.

The risk is truly low, and fatalities are very low, considering the number of sailors never experience an incident in their lifetime. One may argue it’s much less dangerous than driving simply due to the traffic and concentration of vehicles so tightly compact, but a busy day at sea is not uncommon either.

The fatality rate of American sailing is 1.19 deaths per million sailing people. To give you an idea for comparative purposes, snowboarding is 1.06 deaths per million. According to researchers at Rhode Island Hospital, the fatality rate of sailors is higher than that of football players.

The most common reasons that sailors get themselves into harms’ way and increase the danger of sailing includes:

  • High speeds
  • Weather
  • Sailing alone
  • Not knowing how to swim
  • High winds
  • Operator inattention
  • With 15% of sailing deaths being linked to alcohol
  • Falling overboard without a lifejacket (with 82% of drowning fatalities being connected to passengers not wearing a lifejacket or PFD as the law and Coast Guard suggests you always are wearing. Their reasoning and that statistic speaks for itself).

Drowning is the 3rd leading cause of unintentional death worldwide

Is Sailing Good for You?

Absolutely! There are plenty of wonderful health and fitness advantages to sailing, with some being physical while some are more mental.

Some of the key benefits to taking on this sport are:

  • Gaining muscle strength – you’re pulling the ropes, yanking the sails, and moving around the deck. Utilizing your entire body to maneuver this sailboat will work your core, arms, shoulders, and back the most directly, with some of your rope pulls weighing over 50-100 pounds, and some anchors weighing over two tons! You will obviously have an anchoring tool to assist with that, but there will be plenty of other things for you to lift around the deck.
  • One of the most calming sports – with the effects of stress including headaches, depression, anxiety, heart-issues, high blood pressure, heart attacks, lowered immune system, and many other issues, don’t you think a day on the ocean would do your soul some good?
  • The salty air will make you happy – is actually filled with ions that aid our body in absorbing more oxygen and literally feeling better. A day at sea could have your serotonin levels moving closer to the neighborhood they ought to reside in.
  • Improving Communication – you’re working as a team and with a crew. This can be very bonding for creating new friendships and working with people for a common goal.
  • Spatial Awareness Improvement – sailing will aid your spatial awareness in the same way that driving does. The more you do it, the more precisely you’ll be able to really ‘see’ the world.
  • Being one with nature – nature heals, soothes, and restores us, with even Forbes writing about how nature positively influences your health, I believe all of us could use more time outside and less time staring at screens.

There are many other benefits you could fill in between these lines, but it is certainly a sport that we could all use a bit more time enjoying!

A Few More Popular Q&As for First-Time Sailors

Just a few more points to include questions you may be considering as a newbie to the activity:

If there’s a gust of wind, will I capsize?

Turning into the wind will avoid capsizing, meaning, don’t fight the wind’s gust. Turning into the wind will stop the boat. Your sailboat is constructed to resist flipping easily with a heavy ballast and hull to keep the boat centered. You will lean quite a bit, but most likely not capsize.

Is there a high risk of me getting seasick?

You won’t know until you try! It’s absolutely a possibility, and if you get very seasick, then you’ll know once and for all that the sport is not for you. If you only get a little seasick, you can usually avoid it by being well rested, staring at land if it’s in sight, taking an antihistamine such as Dramamine (which may make you sleepy), or investing in a Motion-Sickness Acupressure Wristband. If none of these help, try giving it time or finding a new hobby.

Should I buy a Boat?

My recommendation would be to get certified first and be certain that you love the sport before making a huge investment like that. If you love it and after the first year or so you get tired of going through a rental company, it may be time to consider shopping for your own sailboat. A great starter boat that is more affordable than most (and smaller which will be advantageous when you’re new) is the Sunfish Sailboat Classic, at only around $4,000-$5,000.

What should I look for when buying a boat?

The common things you need to check when examining the quality includes opening the sails, checking for tears, does it have all the seats, is there mildew, are there any holes or are you viewing it off water where you can’t be certain, and inspecting for signs of damage.

The Most Difficult Part of Sailing – Docking

I won’t cover this here because I could write an entire article on docking alone.

Docking is, however, without a doubt, the most common aspect of sailing that you will see mentioned in correlation with its difficulty.

Due to the complicated nature of docking and if you are curious, I would recommend learning from your ASA instructor and with supplemental video training to utilize visual training.

A few popular videos to reference are:

Docking is not a step you will be taking anywhere near your first lesson, so take your time and move gradually forward to the more difficult aspects of the sport.

Get Ready to Sail Around the World!

To sail around the world may take anywhere from one to ten years, depending on how fast you plan to scour the globe! So you better get started now!

My final words of wisdom are to never go out on overly-windy days, talk to lots of experienced sailors, never sail alone (and if you do always include someone on your route and expected time of return), and most of all – have fun!

Sailing is truly a lifetime pursuit, and you will never feel unchallenged. The level of difficulty will depend on your competency and dedication to growing as a sailor. There is always something new you can learn which is the real beauty of sailing.

I hope this guide has been useful to you, and you’re ready to fly across the sea! Once you get started, you’ll wonder why you didn’t begin sooner.

Remember, “Sailing’s easy until you get near something that’s hard.”


I am the owner of sailoradvice. I live in Birmingham, UK and love to sail with my wife and three boys throughout the year.

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