Global HitchHiking, Part II: Sailing Around The World by Crewing: Preparation

Matt Ray
Matt Ray
May 21, 2019 · 7 min read

The first article in this series defined Global HitchHiking. This article will tell you how to prepare yourself to become a Global HitchHiker.

So how do you start Global HitchHiking?

First off, you need to have a desire to be on sailboats and travel the world. Beyond that, there are a lot of variables. I’ve met many people who are Global Hitchhiking and they all want to travel and see things they’ve never seen before. As I’ve stated before, seeing the world by sailboat is amazing, as long is you’re not in a hurry! Regardless, it all starts by having a desire to be at sea on sailboats.

You should have some excitement about sailing. You should also have the ability to sell yourself. You should be comfortable being in small spaces. And you should be able to get along with other people as you may be stuck with them in tight quarters for days and weeks at a time with nobody else around to break up the monotony or tension that may arise. Oh and it might be good for you to know whether you get seasick or not. That can make a huge difference in determining whether you choose to pursue it or not. Luckily, I never get seasick, but have met plenty of people who do, and there’s nothing worse than being seasick on a long passage.

How much experience do you need to start Global HitchHiking?

Everybody I have met has had different levels of experience. Some are just barely getting started and others have lots of experience. That being said, it might be good for you to get some experience sailing, wherever you are. There are local yacht clubs or local classes you can take. Obviously, you would need to live by a body of water or it might be a challenge.

Most yachting organizations have racing activities during the week and are always looking for extra hands or “rail meat” for their races. Rail meat is an affectionate term used for those who sit on the windward side of the boat to keep the boat from heeling too much from the force of the wind or ultimately from capsizing. But even as rail meat, sailing in races is the best and fastest way to get experience with sailing. Most situations require you to think on your feet and respond quickly. The more you know about sailing, the easier it will be to respond to requests from the captain and other experienced “yachties.”

It’s also helpful if you have experience with other things, such as being able to cook, clean, tie knots, and familiarize yourself with sailing jargon. There are lots of resources for this sort of thing on the Internet, all freely available to you. Skippers love to hear that you know how to cook or you know your sailing jargon. If they don’t have to teach you how to tie too many knots or how to tell the difference between the bow and stern of the boat (front and back), it will help persuade them to take you on as crew, regardless of your experience.

Here is a google search for sailing jargon.

Here are a bunch of free courses you can take online to learn about sailing.

Maybe you should also consider getting at least some certifications. The ASA has several courses you can take using self study and exams, such as the 101, 103, 104, and 105. There are commercial courses you can take to get your skippers license and other levels of competency. The RYA also has several levels of competency, such as Competent Crew, Day Skipper, YachtMaster, etc. Just taking the 101, listed above, in the US, would go a long ways towards showing a potential skipper your interest and commitment to sailing.

How I got experience with sailing

Once I got the sailing bug in 2011, I ultimately wanted to get my RYA YachtMaster Certificate, a course that lasts 3 months. But in the meantime I started looking around for sailing opportunities to get more experience before I freed up enough time to go take my YachtMaster Course. Luckily, I lived in Ventura, California, which is right on the ocean, but it was still a challenge finding cost-effective ways to learn more about sailing. The City of Ventura has sailing classes, which are a great way to get started and I’m sure that most cities or perhaps counties, located on or near bodies of water, have similar courses. I just spoke to a friend, who is land-locked in Indiana, but found opportunities to sail with a local club about an hour away from her home.

Join a Yacht Club

I also looked around for a yacht club that would allow me to get more experience and I discovered the motherload of yacht clubs, from my perspective. Fairwind Yacht Club, which operates out of Channel Islands, CA and Marina Del Rey, CA, was the most amazing yacht club I could have found. They are really more of a yacht co-op. In fact, from their website it clearly states:

“…an all volunteer sailing cooperative in Marina del Rey and Channel Islands Harbor, is the ideal way for boating enthusiasts to have year-round access to sailboats without the high costs of ownership.”

If you’re in the Ventura or LA areas, definitely take a look at their offerings. Here’s a link to their Facebook Pages as well. Click on the appropriate links, depending on your location: Channel Islands or Marina Del Rey.

After joining this yacht club and qualifying yourself to sail their first level of boats, you have boats available in each harbor which you can sail, any time during the week. You just have to schedule your sail and you’re good to go. It honestly doesn’t get any better or cheaper than this. Hopefully you’ll have a club near you that can provide these types of inexpensive sailing opportunities. With Fairwind, I got my ASA 101, 103, and 104 Certifications.

Spend Time in Small Spaces

Another thing I did was spend over a year in a tent trailer. Obviously this isn’t required or in some cases desired, but I wanted to see if I could handle living in a small space without going crazy. I called it my “dry run.” This was a experience that I recommend anybody doing, regardless of whether you end up sailing or not. I traveled from California to Vancouver Island and back. Then I did another trip to Miami, up into some of the Eastern States and back. All told I spent 18 months in my tent trailer and I wouldn’t trade that experience for anything. And by the end of my trips, I knew I would be okay to stay in small spaces, such as a mono-hull sailboat. I’ve often called sailing, “RVing on the water,” so living in a trailer gives you lots of good insight about things like solar, waste disposal, small fridges, cramped quarters, all keen insights for the sailing lifestyle.

Formal Training

And lastly, I went to Spain in 2016 and spent 3 months getting my YachtMaster Offshore Certificate, an experience I would highly recommend. This level of training is definitely not necessary for Global HitchHiking, but a great experience of immersion into sailing.

If you have any questions or ideas of things I should add to this article, don’t hesitate to comment or reach out to me. The next article in this series will cover some of the nitty-gritty details of finding boats and skippers and some of things I have done over the past 3 years to find boats.

If you’re interested in more of my writings, take a look at my blog, Living Large by Living Little. If you’re interested in what I’ve been doing in the past few years, this Medium article was written about me. To read the next article in the Global HitchHiking Series, click here: Global HitchHiking III

Here are a few pictures of my Global Hitchhiking for the past 3 years.

Global HitchHiking

HitchHiking Around The World by Crewing

Matt Ray

Written by

Matt Ray

Writings of a world traveler, photographer, computer dude, musician, blogger, and striving minimalist. All pics used are my own.

Global HitchHiking

HitchHiking Around The World by Crewing

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