How to Get Into Sailing (and Why You Should) 

Sailing is an immersive hobby that allows you to enjoy the natural scenery of the open water while remaining physically active. It’s not the perfect hobby for everyone, but it has a ton of advantages for people who love the water.

That said, it’s not as easy to get into sailing as it is some other hobbies; for example, if you want to get into jogging, you can simply find a group, find a trail, and go. If you want to learn how to sail, you’ll need to learn the different types of sailing that exist, get familiar with navigating the waters, and of course, buy an affordable sailing vessel of your own. 

In this guide, we’ll explore the benefits of sailing, and how to get started in the hobby. 

Why Sailing? 

If you’re not sure whether sailing is right for you, you should know there are several advantages to the sport. For example, sailing can: 

  • Provide you with time alone, for introspection. Though you’ll need to be physically engaged and mentally attentive while sailing, you’ll also have plenty of time to spend by yourself, introspecting. It’s a good opportunity to learn more about who you are, clear your mind of distracting thoughts, and just relax. 
  • Give you an opportunity to “get away.” Sailing is a method of travel and it gives you the chance to head far out onto the water, so it’s the perfect method to “get away” from your life for a while. If you need a break from your job or your home life, you can sail away for a bit. 
  • Make you feel empowered with mastery of technical skill. Mastering a new skill fills you with confidence and helps your mind stay sharp. As you become more familiar with the art and technical proficiency of sailing, you’ll feel empowered. 
  • Give you a sense of freedom and exploration. Sailing can also give you a sense of freedom and exploration. Because you’ll have the ability to sail your vessel almost anywhere you want to go, you’ll feel a sense of adventure you can’t quite get on land. 
  • Connect you with nature. Being on the open water is also a great way to connect with nature. You’ll be away from manmade buildings and developments, and if you choose, away from most other people. 
  • Keep you physically active. While sailing isn’t as physically demanding as some sports, it’s definitely a sport in its own right, and you’ll need to be in shape to sail effectively. Keeping control of your vessel and walking around the boat is a great way to stay physically active. 
  • Introduce you to teams and competitions. Sailing is also a popular competitive sport, opening the door to many benefits of engaging in sports. Depending on your priorities, you could get involved as part of a sailing team, or feel the thrill of competition by racing opponents. 

How to Get Started

If you’re sold on the hobby and you’re ready to get started, there are several ways to dip your toes in the proverbial water. If you’ve never been sailing before, you’ll need to learn the skill. Fortunately, there are several ways to do this, such as: 

  • Taking an instructional course. The most straightforward and arguably most convenient option is to take an instructional course. You can sign up for a class in your area and work with teachers hands-on to learn the ins and outs of proper sailing. You may end up paying a few hundred, or even a few thousand dollars for lessons, but the professional skills you learn along the way will be worth it. 
  • Finding a mentor or coach. You could also consider going to local sailing meetups and trying to find an individual mentor or coach who can show you the ropes. In many cases, sailing enthusiasts are more than happy to pass their skills and knowledge on to someone else. Just be respectful of your mentor’s time. 
  • Self-teaching with the help of guides. These days, it’s possible to “teach yourself” how to sail, using a combination of online guides and videos. However, it’s difficult to get the real-time feedback with this method that you’d get by working with an instructor. 

However you choose to learn, you’ll need somewhere to practice. If you’re taking a class or working with a mentor, you may be able to use someone else’s vessels or rent your own. Otherwise, you’ll need to buy a sailing vessel. If you do this, consider buying used to save a bit of money—just make sure you inspect the vessel thoroughly before finalizing your purchase. 

In time, you’ll likely come to appreciate sailing even more. As you develop your skills and become more familiar with the water, this hobby can become very empowering. 

Remember, never travel without travel insurance! And never overpay for travel insurance!

I use HeyMondo. You get INSTANT quotes. Super cheap, they actually pay out, AND they cover almost everywhere, where most insurance companies don't (even places like Central African Republic etc!). You can sign-up here. PS You even get 5% off if you use MY LINK! You can even sign up if you're already overseas and traveling, pretty cool.

Also, if you want to start a blog...I CAN HELP YOU!

Also, if you want to start a blog, and start to change your life, I'd love to help you! Email me on In the meantime, check out my super easy blog post on how to start a travel blog in under 30 minutes, here! And if you just want to get cracking, use BlueHost at a discount, through me.

Also, (if you're like me, and awful with tech-stuff) email me and my team can get a blog up and running for you, designed and everything, for $699 - email to get started.

Do you work remotely? Are you a digital nomad/blogger etc? You need to be insured too.

I use SafetyWing for my digital nomad insurance. It covers me while I live overseas. It's just $10 a week, and it's amazing! No upfront fees, you just pay week by week, and you can sign up just for a week if you want, then switch it off and on whenever. You can read my review here, and you can sign-up here!


So if you’re ready to…..

1) Change your life
2) Travel the world
3) Get paid to travel
4) Create a positive influence on others
5) Be free of offices and ‘real world’ rubbish

Then Sign Up Below and Let’s Get Started!

Follow me on Instagram @onestep4ward