Global Hitchhiking II—How to Prepare for Global Hitchhiking
What to know, learn, and do before you start sailing the world without a boat
The first article in this series defined what Global Hitchhiking is: sailing around the world on other people’s boats by crewing—trading your labor for passage. Now it’s time to explore what it takes to prepare yourself for this wild and wonderful lifestyle.
Let’s start with a simple question:
How Do You Start Global Hitchhiking?
First, you need the desire. If you don’t want to be on sailboats and travel the world slowly, deeply, and off the beaten path… this isn’t for you.
But if the wind calls to you—and you’re not in a rush—then you’re already halfway there.
Here’s what else helps:
A real interest in sailing
The ability to sell yourself and your usefulness to a crew
Comfort in small spaces
People skills—you’ll be in tight quarters with strangers for days or weeks
A sense of humor, flexibility, and a lack of drama
Bonus: Knowing whether or not you get seasick on long passages
Do You Need Sailing Experience?
Not necessarily. I’ve met people with every level of experience—from first-timers to licensed captains. But even a little knowledge goes a long way. If you’re new to sailing, start small:
Take a local sailing class
Join weekday yacht races as crew (even “rail meat” can learn fast)
Look for low-cost lessons or community sailing programs near water
Learn to cook, clean, tie knots, and understand sailing jargon
Sailing Skills Skippers Love
Cooking for a group
Basic knot knowledge (bowline, cleat hitch, figure eight)
Understanding directions: port/starboard, bow/stern
Knowing common terms like winch, halyard, head, and galley
The less they have to explain, the more likely they’ll say yes to you joining them. There are hundreds of sites online that will cover all of these topics, including YouTube sites that can show you exactly what to do and learn.
Training & Certifications (Optional, but Helpful)
If you want to level up your skills and credibility, consider these:
ASA Certifications (in the U.S.): ASA 101, 103, 104, 105
RYA Courses (international): Competent Crew, Day Skipper, YachtMaster
Even the ASA 101 or RYA Competent Crew course shows you’re serious. Some yacht clubs or boat groups may require them, too.
How I Got Experience with Sailing
I caught the sailing bug in 2011, on a week-long trip to Belize on board a 40-foot catamaran. My ultimate goal was to get the RYA YachtMaster Certificate, but that requires a 3-month commitment in Europe. I knew I needed more experience before taking the plunge.
Here’s what I did:
Took city-run sailing classes in Ventura, California
Joined Fairwind Yacht Club, a co-op-style club in Channel Islands & Marina del Rey
Sailed regularly with Fairwind, earning ASA 101, 103, and 104
Lived in a tent trailer for over a year as a “dry run” for boat life
That trailer experience taught me a lot—solar, small fridges, waste systems, tight spaces, and mental resilience. Sailing is often called, RVing on water.
Consider a Local Yacht Club
Yacht clubs can be expensive… or incredibly affordable.
Fairwind Yacht Club was a game changer for me. It’s a volunteer-run co-op with boats you can sail anytime once you qualify. Membership is reasonable. Training is hands-on. And the community is gold.
“Fairwind Yacht Club… 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.”
Look for similar clubs in your region.
My Final Step: Formal Training in Spain
In 2016, I spent three months in Spain earning my YachtMaster Offshore Certificate. It’s not required for Global Hitchhiking—but it gave me a depth of knowledge, confidence, and sea time that helped me to be a more proficient crew member/Global Hitchhiker.
If you’re committed to the sailing life, formal training is worth it.
Coming Next in the Series
In the next article, I’ll dive into the practical details of finding boats and connecting with skippers. This includes the websites I’ve used, the profiles I built, and the messages that got real results.
🧳 Global Hitchhiking III—How to Find Boats and Start Crewing
🛟 Global Hitchhiking IV—Safety Considerations While Crewing
🚺 Global Hitchhiking V—Safety Considerations for Women Crewing
If you want to return to the first article in this series, it is here:
🌍 Global Hitchhiking—How I Sailed Around the World Without Owning a Boat
Thanks for reading. If you enjoy posts like this—where travel, truth, and story all intersect—consider subscribing and following. I write about sailing, cybersecurity, AI, and adventure, with a few detours into the absurd.
⛵🧭
Matt Ray
Living Large by Living Little
About the Author
Matt Ray is a sailor, writer, and cybersecurity tinkerer. He once circled the globe by hitchhiking on sailboats—and somehow lived to write about it.
Note: This article was originally published on Medium. It has been revamped and republished here on Substack.