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How Long Does It Take To Learn To Sail And How hard Is It? 12 Great Tips To Get You Started

Learning to sail is quick and easy. Learning to sail is not hard or time consuming. Let’s get that out of the way. There is a perception that sailing looks like a ton of work and is really complicated and nothing is further from the truth. I’ve sailed for a long time on many types of boats and spent a few summers working as a childrens sailing coach. So let’s answer the question of how long does it take to learn to sail and how hard is it to learn to sail?

1 – How long does it take to learn to sail?

How long does it take to learn to sail? You can learn to sail in a few hours. That is really all that is needed to learn the basics. I learned to sail as a kid with my dad at the local lake on Sunfish. After a 4 hour morning lesson, we could sail the boat around the lake and be able to rent boats at that lake after that. We learned how to raise and lower the sails, tack upwind, reach and sail downwind. We also learned how to upright a boat if we capsize and get back in. Sunfish are really simple boats and easy to sail. That is sailing.

If you want to learn to sail a 40 foot cruising sailboat with a diesel engine the process is a lot more involved. Sailing is sailing. That doesn’t change. Sails get bigger and lines get harder to pull. There are a lot more skills to learn such as starting and stopping the engine, using winches, docking, etc…

We had the dream of cruising around the Chesapeake so we took a cruising boat class from Annapolis Sailing School. The class was for 3 or 4 days. They taught us how to use winches safely, how to start and stop the engine, and how to dock and tie up the boat. After that, we had enough knowledge to rent/charter 30-40 footers on the Chesapeake.

2 – How hard is it to learn to sail?

How hard is it to learn to sail? It’s really not very hard. It’s quite easy. In essence you can raise and lower a sail. You have one line called a sheet to control the position of the sail. You have some way to steer the boat. You steer the boat the direction you want to go and use the sheet to adjust the position of the sail so it’s not flapping around. That is 99% of it. It’s really very basic. Even 5 year old children can learn to sail on their own in their own boat. Any other lines and controls on the boat are just fine tuning.

Below are a couple videos that show how to sail.

3 – Where do I learn to sail at?

There are many places you can learn to sail. There are places like the American Sailing Association certified sailing schools. Sometimes there are local lakes or Universities that may offer sailing classes. If you have a friend with a sailboat there is a good chance they will teach you if you ask.

A really good free way to learn to sail is try to go racing on a sailboat? What you say? You don’t know how to sail so why would someone take you out on a racing boat. People who own racing sailboats always need crew for their boat anyone willing to learn makes a good crew.

Many yacht clubs or sailing organizations have crew boards such as the local one for Detroit Sailing, DRYA. You’ll pick up the basics of sailing after your first race even if you knew absolutely nothing at all when you stepped on the boat.

getting ready to sail at yacht club

4 – Do I need to know how to tie a lot of knots to sail?

You don’t need to learn to tie a lot of knots to learn to sail. On many boats everything is attached with shackles, clips and cleats so you don’t have to tie knots. There are 2 or 3 very helpful to know knots. A figure 8, bowling and cleat knot. You can click here to learn any knot you would ever need to know on a boat.

5 – How can I teach myself to sail?

Can you teach yourself to sail? Yes, you probably can. Read a book or watch a YouTube video. It’s not that hard and I know many people who have learned to sail this way after going out and buying a boat. It’s probably not the best idea to go buy a boat and just go out without doing a little bit of research first.

If you want to teach yourself to sail pick a good day for it. Wait for a day when the wind is calm. Less than 10mph with no storms in the forecast. A day with a 30% chance of thunderstorm seem to be almost a guaranteed severe storm day.

6 – What is the best boat to learn to sail on?

The best boat to learn to sail on is something simple and stable. The size doesn’t matter all that much. You really don’t want a high performance racer that has a million lines and blocks running around. I learned to sail on a Sunfish which is a very simple 14 foot sailboat. It has one line to raise the sail and one line to control the sail. You really can’t get much more simple. They are very sturdy and pretty stable also. I think these are pretty ideal boats to learn on.

A lot of yacht clubs like to use Flying Scotts. They are 19 feet long and pretty slow and stable and don’t have a ton of lines on them. They are another really popular learn to sail boat.

They don’t capsize easily. Some places will teach sailing on keelboats. Keelboats are larger sailboats that have a lead keel on the bottom to keep them from capsizing. Keelboats have a lot of momentum and they don’t react that quickly.

In essence the best boat to learn to sail on is the boat at the location where you can learn to sail is. You can learn to sail on almost any boat in the proper conditions which is a light breeze. You can ignore most of the lines except for the line that raises and lowers the sail and the sheets that control it’s position.

The only truly bad boats to learn to sail on would be a really high performance boat such as a foiling Moth or skiff such as a 49er that is a double trapeze boat. These boats are extremely unstable even in light winds and you’ll spend your entire time swimming and you’ll probably brake something on the boat.

See our article on the best small sailboats for beginners to learn more about boat choice.

sailboats sailing together

7 – Is any boat too big or small to learn to sail on?

No boat is really too big or too small to learn to sail. You can really learn to sail on any size boat. The bigger the boat is the less you will feel anything and the slower it will react. On a 14 foot Sunfish you’ll hold the steering tiller in one hand and the mainsheet to control the sail in the other and you’ll feel everything.

On a 30 foot keelboat you’ll probably just be holding one line or steering the boat. You won’t feel any subtle changes due to small adjustments in the sail position. On an even bigger boat you’ll feel even less. The ideal size for learning is probably somewhere in the 14 to 20 foot range. You can have a very stable boat that still lets you feel everything.

8 – How do I learn to go cruising with my sailboat?

If you live somewhere that is good for cruising such as the Chesapeake Bay, the Florida coast or the Great Lakes chances are you’ll want to go exploring with that boat you’re looking to buy. How do you learn to do that?

A really good option is taking a bareboat charter certification course. That will teach you everything you need to know about operating a larger boat and navigating the waterways. Racing on someone larger boat is a good way to pick up a lot also because navigation is an important point there too.

Other ways to learn the skills are if you’ve got a friend with a boat who likes cruising and they can take you somewhere. If you don’t know anyone, crewing on someone’s racing boat is a good way to meet someone since many of these boat owners go cruising with their boats also.

cruising sailboat in marina

9 – How do I learn to charter a cruising sailboat somewhere?

Everyone has that dream to go sailing off in the islands or some other cruising destination. How do you go about chartering a boat? What do you need to learn to be able to do it?

Most charter companies will want you to have some kind of certification proving you took lessons somewhere or a resume of your sailing experience to show you won’t go out and destroy their boat. The American Sailing Association has a listing of schools that offer bareboat chartering certifications. There are some other organizations as well.

Here is a good article from Sailing Magazine on how to get bareboat charter certified. I took a class with my dad in Florida years ago and it was a really good time. The classes consist of taking a boat out for a few days sailing around to learn how to operate the boat, the engine, and docking.

10 – How do I learn to race sailboats?

If you are interested in racing sailboats, the best way to learn to race is going out and crewing on someone else’s boat. The easiest way to learn what is involved is by experiencing it. There are sailing schools that do cater to racers and advancing your racing skills. J-World is a really good example.

11 – How do I learn to cross an ocean?

This is something I have never done and I’ll admit I don’t have a lot of desire too. If this is your goal in sailing, you’ll want to learn all you can about keelboat sailing. You’ll want to start by doing smaller passages and working up to it. There is a whole higher level of wind and sea conditions you can get on the ocean that you need to learn to deal with.

This is an area where you really need to do a lot of research to prepare correctly and find a suitable boat. Most boats out there are what is considered “coastal cruiser” and not made to handle what you might run into crossing an ocean.

12 – I want to buy my own boat. What should I learn?

How big of a boat do you want and what do you want to do with it? If your interested in a small day sailor for the local lake then you need to learn the basics of sailing and not much else.

If you want a 30 foot cruiser than you need to learn a lot of other skills such as docking, maintaining an engine, bottom painting and launch prep, and many other skills. All of these can be learned along the way if you take it slow. If you buy a boat and try to teach yourself to sail it, choose a calm day with a light breeze. Don’t go out the first time on a day it’s blowing 25mph winds with large waves and try to learn on that day.

sailboat cruising on the lake

Time to go learn to sail

I hope this article gave you the answers you are looking for. If not please feel free to ask it in the comments below or send me a note. You can look me up on social media and ask there too. I love discussing this topic and helping new sailors.

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About the author

My name is Doug Ryan. I am an outdoors enthusiast always looking forward to my next adventure. I spend as much time skiing, biking, and paddleboarding as I can. I decided to start Endless Rush Outdoors as a way to share my knowledge and enthusiasm for all things outdoor adventures and to help other people have as much fun as me.

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