Becoming a Sailor, Where Do I Start?


It’s this kind of picture that infects people with the sailing disease

You have this romantic vision of a beautiful sailboat at anchor. You want to untie the bowlines and sail off to the horizon. But you have never set foot on a sailboat before. If you know nothing of sailing, how do you realize that dream? Where do you even begin? These were the questions I faced a few years ago.

Since then, I have learned to sail, bought a boat, and made my first dream trip. With this article I want to share my experiences and offer advice. I do not intend to provide the final answers to everything. Rather, the advices in the article are based on the choices I made and how I would have done things differently in hindsight.

So if you want to make a big sailing trip, but have zero experience, how can you make it happen? Here’s a walk-trough.


And this one..

Step One: Don’t Buy a Boat Just Yet
After having decided that they want to pursue their sailing dream, a lot of sailing novices start out by asking which kind of boat they should buy. I think this is a fine example of asking the right question at the wrong time. Yes, buying a boat that fits your needs is very important. But if you have little or no sailing experience, you do not yet know what your needs are..

When I became enthusiastic about sailing, I fantasized about boats with big cabins, (or at least, the biggest cabin I could reasonably afford). I thought it would be really cool to travel the world and have a floating apartment at my disposal. But after my first two years of actual sailing, I found out that the way a boat handles under sail is much more important to me than living space. I like the direct feedback small boats give me. If I would have bought a boat before I had some sailing experience, I likely would have ended up with a boat that does not fit my needs as well as my current boat does.


Or this one

Step Two: Take Lessons. In an Open Boat, Preferably
A lot of the seasoned yachtsmen (and women) I meet at the marina started their sailing career as kids, sailing little open boats on a sheltered lake. They gradually moved on to sailing larger boats. I think this is the best way to learn. As mentioned before, smaller boats give more direct feedback than bigger boats. Also, they are simple to operate. Ever seen all the lines on a typical sailing yacht? Most open dingy boats are sailed with just two or three different lines. Pretty simple, pretty straightforward. You will pick up the basics quickly, perhaps in one or two weeks worth of lessons. I did not take any dingy lessons, but went straight on to crewing bigger boats. That meant that I was slow to understand what was going on. My progress would likely have been faster if I had developed a ‘feel’ for sailing on an open dingy boat.

Step Three: Charter and Crew
Now that you have acquired the basics, it is time to make some flying hours. In my opinion, the best way to do so is by chartering boats. You can buy lots of cheap, second hand boats on Craigslist, often for no more than a few hundred bucks. They look ideally fit for the purpose of messing around on the water. However, these boats are cheap for a reason. They often need a lot of maintenance. Not ideal if your goal is to acquire some experience, in my opinion. For the first two years I and my boyfriend chartered every now and then. For us, that was perfect. We avoided the hassle that comes with owning a boat. Chartering also gave us the opportunity to try different boats.


Maybe this one

There is a classical pitfall to chartering: picking a boat that is to big for your experience. A 40-foot yacht is quite something else than an open dinghy. The fact that the charter company trusts you with their boat does not really say anything. They are insured with high deductible excesses, so if you break something you will be the one paying for it. They want to make money, and couldn’t care less about possible damage. I have seen overconfident charter captains slam in to other boats on multiple occasions. So, better start small. In the Netherlands, you can charter a 22-foot yacht for 200 euros a weekend. We learned a lot by messing about in a 22-foot boat!

It is possible to combine making some flying hours with a sunny holiday. These holidays are offered in most sailing hotspots, like the Mediterranean and the Caribbean, but also South East Asia, the UK, Holland and many other places. There are several options. Flotilla holidays are perfect for beginning sailors. You charter your own boat, but you will sail in a group of boats, guided by a flotilla leader. He or she will help you with the difficult bits, like docking and mooring. If you do not yet have the crew or confidence to skipper your own boat, there are also holidays available where you book a berth in a yacht, and assist the skipper. Another option: a holiday that is at the same time, a sailing course. You sleep on a yacht which you sail around for one week or two, practicing everything that comes with skippering a sailing yacht. If you are confident enough, you can also opt for bare-boating: chartering your own yacht with no expert guidance at all.


How about this one?

You can also choose to crew other people’s boat. On message board and forums, there are often people looking for crew. They want to sail from A to B, but do not have enough crew or time to do this all by themselves. This is cheaper than chartering, but if you have very little experience, you are not going to be of much help to the rest of the crew. Still, it might be possible that someone is willing to take you aboard, to share the joy of sailing with others. Whether it is actually helping out or just being introduced to sailing on a yacht, you will have the best chances if you are an active member, who contributes to the group.

Step Four: Now You Buy a Boat
After you have gained some experience, have seen different waters and different circumstances, you will start to get some ideas of what your ideal boat might look like. Now is a good time to start looking around for your very first sailing boat. Probably, at this stage, you will already be somewhat familiar with the most common boat types, and how those types may fit your needs. Here again, the message boards are a big help. They offered me tons of advice. One of the users informed me of a certain boat that was up for sale. That led me to the boat I have today.


Perhaps this one

Step Five: Ask More Advice. And More. And Even More..
After you have bought your very first boat, you will need to spend some time together. Time to get to know her, in the water and in the boat yard. You are going to ask the message boards tons of questions. At least I did. At times it felt like somebody delivered a live horse to my doorstep. So, okay, I have a horse now. What does a horse eat? Can I leave a horse outside for the night? Are there things that I am not aware of, that are particularly dangerous to a horse? What else does a horse need?

Step Six: Sail off..
But relax. Soon, you will notice that you get the hang of this boat maintenance thing. You will learn by doing. You discover that you are changing in an actual handy person. And at the same time, you will expand your sailing experience and gain more confidence. And sooner or later, you will feel that you are ready to untie the lines for that one dream trip..

Good luck!


And of course, this one!




Leave a Reply

Your email address will not be published. Required fields are marked *