Global Hitchhiking IV — Safety Considerations While Crewing
How to vet boats, skippers, and situations before setting sail
Not all sailboats—or skippers—are created equal.
This part of the Global Hitchhiking series is about safety: how to choose the right boat and the right people, avoid unnecessary risks, and learn from the hard lessons I picked up along the way.
A separate article will address crewing as a woman, with specific risks and considerations. For now, this piece covers:
Boat safety
Skipper qualifications
Red flags
Social safety
And a long, cautionary tale about one boat I should’ve left sooner
⛵ Is the Skipper Qualified?
There are no universal requirements to be a skipper. Anyone can buy a boat and start sailing around the world tomorrow—whether or not they’re competent or prepared.
That means you need to ask:
How long have you been sailing?
Where have you sailed?
Do you hold any certifications? (ASA, RYA, YachtMaster, 6-Pack, etc.)
You don’t need to interrogate them. But you should understand their level of experience before committing to weeks at sea under their command.
🍻 What About Substance Use?
One big red flag: skippers with alcohol or drug problems.
You may not notice it right away. I once sailed with a skipper who had a “dry boat”—no alcohol allowed. I later realized that was a warning sign. He struggled with drinking and couldn’t handle the temptation, so he opted to have a dry boat instead.
When we arrived in Indonesia, we decided to buy some beer, since we had been sailing together for over a month. That skipper started “sneaking” beers and ended up dropping anchor on a beautiful coral reef in Raja Ampat, one of the most prestigious diving spots in the world. We gave all the beer away at that resort, to prevent future concerns.
If the skipper is drunk at your first meeting, it’s probably not a good boat to join. If they’re irritable, erratic, or cagey about their habits—think twice.
🚧 Is the Boat Safe?
Even a great skipper can only do so much with a poorly maintained boat. That’s why I’ve created a safety checklist to help guide your questions. You don’t need to be an expert—you just need to care enough to ask.
🧾 Boat Safety Checklist (Abbreviated Highlights)
Lifeboat and grab bags? Has the lifeboat been serviced recently?
EPIRB on board? Battery tested?
Standing rigging (the cables that hold up the mast): age, condition, signs of rust? There’s no reason you can’t walk around and physically inspect these.
Running rigging? These are the lines that hoist the sales. Are they in good condition?
Engine: Is it reliable, been recently serviced, are there backup options? Is the cooling system working? How do you start and stop the engine?
Auto-pilot. Is the auto-pilot working? Is there a wind vane? What are the plans if the auto-pilot fails?
Emergency steering. Does the boat have hydraulic or direct steering? Is there an emergency steering procedure in place in case the steering fails? Has it been tested? Broken rudder, hydraulic leaks, or other things can cause a steering failure.
Bilge pumps in working order? Is there a manual bilge pump in case the electric ones fail?
Fuel systems: Is there a fuel cleaning system on board? Are there replacement filters. What is the capacity of the fuel tanks? Are there spare jerry cans of clean fuel on board?
Sails: Are they in good working order, usable, patched, if needed, and are extras available?
Navigational tools: VHF, AIS, chart plotter, GPS, backups (e.g., paper charts)?
Solar or wind power? Enough juice for lights/nav/charging through the night? Is there a generator on board or is the engine required to charge the batteries if solar or wind aren’t working?
Flare kits, fire extinguishers, and fire blanket?
First aid kits on board?
Working dinghy with strong motor?
👉 If you’d like the full checklist as a downloadable Word/PDF version, just let me know.
⚠️ A Personal Example: When It All Went Wrong
My first crewing experience should have taught me to walk away. But I stayed—and I learned the hard way. It was my first experience, and I was excited!
Quick hits from that voyage:
Boat had no auto-pilot (hand steering 24 hours a day if at sea)
Rigging failure (rusted bolts) caused us to turn back to port on one passage to the Bahamas. We were lucky we didn’t get demasted.
The steering failed due to leaking hydraulic fluid line
The main sail was torn, completely unusable
No viable emergency steering system
Some bad fuel we purchased killed both our engine and generator mid-passage in the middle of the ocean
We had no tools to replace the fuel filter
We ended up making a Pan-Pan distress call to get help—but that began 7 days of hell at sea, not to mention hand-steering the entire way and having to top off the leaky steering system the whole way.
Would I recommend doing what I did? No. But I’m grateful for what I learned, and I’ve never sailed on a boat with those problems again—because now I ask the right questions.
🧑🤝🧑 Social Safety: Don’t Sail With Assholes
Boat safety is only half the story. The other half is social compatibility.
You’ll be in a confined space with this crew—days or weeks without breaks, privacy, or sleep. That means you need to ask:
Does the skipper treat others with respect?
Do they get along with locals?
Are they controlling, irritable, temperamental?
Is the boat a dry boat? How do they handle alcohol?
Do you feel safe, emotionally and physically?
A Skipper I Should’ve Avoided
In Tahiti, I felt pressure to jump on the next boat. I rushed. I ignored red flags.
The skipper cursed at a child in a restaurant
He seemed charming at first, but he was a narcissist, who criticized me for everything I did and used personal stories I shared with him against me
The tension got so bad, I snorkeled from boat to boat in Bora Bora asking to crew elsewhere
I finished the three-week leg to Tonga with him, but it was brutal. After he left for a family emergency, I found a new skipper—one of the best I’ve ever sailed with. We went all the way to Malaysia together.
That contrast taught me everything I needed to know about choosing the right people.
Final Thoughts
You’re not just picking a boat—you’re picking a survival pod.
Ask the safety questions. Don’t let inexperience keep you from asking them. It’s your life on the line.
Pay attention to personalities. And give yourself the grace to say “no” if it doesn’t feel right.
I stayed too long on my first boat because I was eager to learn. I stayed on the other boat with a toxic skipper because I didn’t have the funds to spend money on a hotel in Bora Bora. Those decisions nearly cost me peace, health, and safety.
You don’t need to make the same mistakes. If you ever feel in danger, from the boat or the skipper, jump ship as soon as you can safely do so.
Next in the Series
The next article in this series discussed special considerations for women Global Hitchhikers.
🚺 Global Hitchhiking V—Safety Considerations for Women Crewing
To return to previous articles in this series, the links are here:
🌍 Global Hitchhiking—How I Sailed Around the World Without Owning a Boat
🧭 Global Hitchhiking II—How to Prepare for Global Hitchhiking
🧳 Global Hitchhiking III—How to Find Boats and Start Crewing
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.