Sailing Is A Lot Of Work But Totally Worth It (Beginner’s Advice)

Being on the water with the wind driving your sails is a great feeling, but there’s usually a lot that goes into it.

What does it take to go sailing?

Here’s How Much Work is Required to go Sailing:

It takes years to become a seasoned sailor with the skills and knowledge to stay safe and efficient on a sailboat. Sailors require several days of intense instruction will be required. Captains will have at least a season of learning and experience, plus all the time required to maintain the boat.

How Long Does it take to Learn How to Sail?

If you want to be a crew with 1 job, then 1 lesson will do.

If you want to understand all the aspects of sailing, 10 days should do.

For instance, if your skipper wants you to be the genoa trimmer and not pay attention to anything else, you’ll be taught to read the tell-tales and what to do when tacking or gybing. You’ll be ready to help crew as a genoa trimmer after one lesson.

You’ll learn to adjust as the wind changes and read shifts on the water before they reach the boat, for instance. Some sailors can be practically ready to sail and contribute after one lesson, but after only one day, you will not be in charge of anything important and will only take orders from experienced sailors.

With experience, say a season, or so, you will understand how to trim all the sails and perform all the functions on your friend’s boat, including steering, and do them all at a proficient level, and you will only get better with time.

This is harder if you are learning how to race sailboats, as time, speed, and recognition are prominent factors, but you will still know what your primary job is after a week of learning.

If you go all-in with your time, you can learn all the basics in about 3 days to 1 week. This is about the average length of the adult sailing course, and it varies from region to region and depends on the organization you are going with.

If you are skippering a dinghy, this same amount of time is about accurate.

How Long Does it Take To Become a Captain?

Being the captain of a keelboat is another story.

In addition to the functions of the sailboat like steering and sail trim, you need to understand navigation, weather, how to use radios, safety procedures, docking procedures, and the sailing terminology, in addition to boat maintenance and repair.

Many sailors have over a year’s worth of experience on the water and at least 90 days of prep and training before taking courses or exams that allow them to become licensed captains. Others will go to sailing schools that promise all the captain’s training they need within 2 weeks.

It is important that someone new to sailing does not attempt to become the captain of a commercial or charter boat until they have had at least a year or more of experience, but those who own their own sailboat and want to learn the basics to take it around the lake may learn within a shorter amount of time.

Now, as mentioned, you can get certification in about 2 weeks through a variety of courses and organizations, but most captains have had a lot of experience in the field as sailors before they ever try to become a captain of their own ship.

Certification makes it a lot easier to charter a boat, for instance, but that doesn’t mean you’ll be prepared for the real dangers or problems that might occur on the water.

How Much Does it Cost to Learn Sailing?

There are a lot of ways to learn to sail.

Some of them cost nothing at all, while others can cost quite a lot.

Exams and license certifications can also cost money, so be prepared for expenses when you apply to become a commercial or charter crewmember or captain:

Free Learning:

For many people, learning how to sail costs nothing at all.

If you have a friend who owns a dinghy or a keelboat, they may be delighted to have you go sailing with them. All you have to do is ask!

Another potentially free way to learn is to volunteer as a crew at a yacht club. Most yacht clubs will do casual races during the middle of the week, and there are almost always skippers looking to fill out their crew.

In this case, you may be ballast or make sandwiches for the first few races you go on, but if you demonstrate a willingness to learn and show yourself to be dependable as a crew member, you will, in all likelihood, find a regular ride on a boat.

That can lead to a years-long relationship and building a deep knowledge of sailing, all for free.

Sailing Courses:

If you opt to take a sailing course, either locally or through a national organization like US Sailing, American Sailing Association, or the Royal Yachting Association, it will cost you some money.

The cost will depend on whether you want a beginner’s course or something more serious like getting your International Proficiency Certificate.

For instance, the American Sailing Association 101 Basic Keelboat Sailing course taught at the Annapolis Sailing School takes place over 3 days and costs $750. You end up with a basic certification with a solid understanding of sailing.

They also teach three other ASA courses there, such as ASA 105, Coastal Navigation.

Each ASA school has a different price and teaches different courses; for instance, the ASA 101 in Seattle may cost as little as $395 if you are a member of the Seattle Sailing Club.

The US Sailing Basic Keelboat course teaches the same basic things, though the courses are regulated a little more strongly by the national body. The length and cost vary again from school to school.

As an example, the Hampton Yacht Club teaches to its members over two days for $280 and a supplemental course that includes better sail trim for another $140. They will also teach non-members, but the course costs more, usually $100.

If you wish to get your International Proficiency Certificate to charter a boat almost anywhere in the world, you will need to take several different courses offered by ASA or US Sailing (if you are based in the US) and then pass further testing.

There are also a variety of private lessons offered by individuals or local organizations. Unless they are accredited by US Sailing or ASA or RYA or some other organization, you will not be certified afterward. But you still may gain a lot of knowledge, potentially more than an official school.

It is best to do some research on these local, unaffiliated courses before signing up for them. They may cost anywhere from $50 for a single day’s instruction to over $1,000 for two weeks of direct, one-on-one instruction.

How Much Work is Required When Owning a Boat?

The majority of the work required when owning a boat is in maintenance.

Many owners can pay others to take care of their boats, but the majority of boat owners end up doing their own maintenance, either because of the expense to pay others or they want to make sure it is done to their satisfaction.

You can generally break maintenance down into yearly and weekly tasks.

Yearly maintenance doesn’t necessarily need to be done every year, but the boat needs to be inspected in case it has to be done:

The Particulars:

Hull paint, including bottom paint for keelboats kept in the water, needs to be watched.

It may need to be re-applied (particularly bottom paint, so you do not get growth or even barnacles), but at a minimum, it needs to be polished and treated. Inspecting for damage to the fiberglass is important, as well, at this point before the problem grows, like water getting inside of it.

Sails need to be inspected yearly, looking for problems such as stitching worn away or degraded by the sun (particularly in furling covers). Damage from wear or chafe should be caught here before it develops into a larger problem.

Here are a few things to put on your checklist:

  1. Rigging should be inspected, including the wires themselves and any terminals and swages.
  2. Check the mast and the spreader.
  3. Safety equipment should be inspected to ensure it is in working order and up to date.
  4. Engines need to be inspected, as well.
  5. Any woodwork will need to be treated.
  6. Teak should be cleaned and treated yearly to maintain it; this is far cheaper and less work than replacing it!

There are also weekly or even daily tasks that should be done for keelboats sitting in slips over the year:

  1. Docklines should be inspected to make sure your boat responds properly to tide changes; they may need to be adjusted.
  2. Check any electrical cables you have going to the boat, such as for shore power.
  3. Inspect the bilge to make sure there is no water and that the bilge pump is working properly.
  4. You will also want to check your battery and the electrical system regularly.

Over the course of the year, you will find things that need to be repaired or replaced; that is the nature of boat ownership. You will most likely spend more time in maintenance than you do when sailing.

You can expect to spend $2,000 to $5,000 on maintenance in a year in addition to the time you will be putting in, but for most, this is totally worth it!

How Many Hours of Work Before You’re on the Water?

The amount of work required before you are on the water varies with the kind of boat you own, as well as your storage or docking situation.

Ironically, most keelboats are easier to get going than dinghies. This is because they are docked.

Depending on how far your dock is from where you park your car, you can have the day’s supplies loaded and be underway in 15 minutes.

If you and one or two other people, all you have to do is park, take your food and clothes down to the boat, start the motor, and cast off the lines.

If you have more people or are leaving on a longer trip, it will take you longer to load your boat and arrange the storage situation. If you have a larger boat, it may require more time as well. Still, even in the worst cases, you should be able to get your crew and their belongings on the boat and get underway in half of an hour to an hour.

Large Boats Vs. Small Boats:

The exception is if you have a very large boat.

You will probably have a routine you go through in preparation and have the engine running at the dock for a while before departing. In the case of a 60-foot boat, you should still get underway in less than two hours.

Dinghies are a different story. This is because most of them are on trailers.

You certainly won’t have as many supplies to pack onboard, but launching the boat will take some time, particularly if there is a line to the boat ramp.

Some dinghies are light enough to be car-topped rather than trailered. You won’t have to wait in line to launch them, but you will still need to carry them to the water.

Regardless of how you launch your dinghy, you will need to step the mast and rig the shrouds and then put the sails on. Depending on the kind of boat you have, you may do this before floating the boat off your trailer.

All of this may take an hour or more, depending on the size dinghy you have and the number of others jostling for launching space.

Some people living on the water may have a boat like a catamaran ready to launch off their beach. In this case, it will be a matter of minutes before you shove off and are under sail.

In some situations, such as distance catamaran racing, it can take two or more hours to prepare your boat and the rigging, get it launched, and raise the sails, but in most cases, you will be sailing your boat in under an hour.

What Type of Sailboat Should a Beginner Choose?

For an absolute beginner, they should get a dinghy that is simple to sail:


One of the most popular boats in the world is the Sunfish.

It is a very forgiving boat that is easy to sail, and the crab claw-style sail is an efficient design for ease of rigging and handling.

Even experienced sailors can have fun in a Sunfish.


A Laser is also a good boat to start in.

Another boat with worldwide popularity, the Laser is easy to sail but difficult to master, allowing for a lot of growth.

Hobie 16:

Many sailors along coastal regions get their start in a Hobie 16.

While a more complicated rig than a Sunfish, the Hobie 16 has much higher performance, meaning many people find it more fun.

While catamarans are more difficult to handle, the Hobie 16 can be mastered over a few weeks of handling.


For young children, Optimists are an iconic class.

They are small and simple but allow some room for potential growth.

Many clubs have Optis for their members’ children to learn in.

What Boat Size for Beginners?

If you are a beginner but want to start in a keelboat, there are many choices, but it is probably best to stay around 26 feet or less.

This gives an amount of sail area that you can handle with a smaller, inexperienced crew, and even single-hand if you want, but enough room to experience the joys of keelboat sailing.

There are thousands of used boats on the market to choose from, but boats known to be beginner-friendly in that size are the Pearson 26, the Cal 25, the Columbia 23, and if you are interested in more performance, the J-22 or the J-24.

Many clubs have Sonars now as their adult sailing trainers, and they are easy to handle. There are many of them on the secondary market.

If you are looking at doing overnight sailing, they are not the best choice.

Most sellers, whether private or a dealer, will take you out on a test sail, and that is highly recommended for a beginner, as you need to be confident in a keelboat that you are looking to buy.


ASA 101 School Costs

US Sailing Basic Keelboat Course

Hampton Yacht Club Adult Sailing

Winter Boat Checklist – Sailing Today

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