Q&A: Circumnavigating Without a Boat

And How the Author Was Disuaded From Sailing as a Job

Peter Swanson Apr 7

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This is the Amazon blurb for Matt Ray’s book: A no-nonsense, practical guide to crewing on sailboats and crossing oceans as a working guest, not a paying tourist. Based on three years of experience hitchhiking over 30,000 nautical miles, Matt Ray breaks down how anyone can get started—whether your goal is a short coastal hop or a long-haul ocean crossing.

Loose Cannon: This is a chicken-egg question. Did you set out to hitchhike the world on boats to write a book, or did the idea only come to you as were underway?

Matt Ray: I didn’t set out to hitchhike around the world or write a book. I had just finished my RYA Yachtmaster in Spain and was considering a shift from IT into sailing. But between being colorblind—which limited my certification—and starting later than most, the traditional path didn’t make much sense.

So, I started crewing to get experience and miles under my belt.

One boat turned into another—Virginia to Aruba, Panama to Tahiti, Tahiti to Tonga. It wasn’t until the next leg, Tonga to Malaysia, that I realized I could just keep going west and turn it into a full circumnavigation. Up to that point, I wasn’t chasing anything. I was just sailing.

The writing came even later. I started blogging between Malaysia and South Africa, mostly to explain what I was doing and what I was learning along the way. Those articles eventually became the foundation for this book.

I’m now working on a memoir that tells the full story of the three-year journey, along with a photo book to go with it.

L.C.: Ha! A late British friend of mine managed access to somehow to memorize the color blindness test for full certification. He once ran my boat aground because he didn’t recognize a small red nun for what it was, but other than that he was a good guy to sail with. Can I assume that most of your interactions were positive or you would not have kept at it?

Ray: Yeah, I actually went to South Hampton to the RYA headquarters right after my RYA Certification, to get a lantern test, hoping it would be less stringent than those picture book tests. But it was very telling. They simulate darkness and distance, and drop red, green, and white dots on the wall, to simulate a ship passing in the distance. For me, the green lights looked white. I couldn’t see the green lights. I could see the red and obviously the white, but those greens just disappeared at night. Failed test objectively.

All of my interactions with skippers and boats were positive except for one. I had a skipper from Tahiti to Tonga who turned into the worst skipper I have ever encountered. I wrote about this extensively. Sailing to Bora Bora is an article that goes into a lot more detail about that experience.

The skipper between Australia and Grenada (a year of travel together) and I had personality conflicts. We got along as long as we agreed with each other. I didn’t mind him as long as there was at least 1 other person on board with us. I think if I had sailed with him alone for an extended period of time, I may not have lasted a whole year with him. There were times when the other shipmate and I had to rise up in rebellion when we disagreed with him. But ultimately, it was his boat and his final say on everything.

L.C.: I’ve always believed that three was better than two on a boat. And, in general, an odd number is better than even. Yes, the captain in theory rules but sometimes you need a consensus (this can be for a variety of reasons) and with an odd number, you can’t deadlock.

If you will allow me an “interview question,” could you share with the readers both the high and low moments on your adventure?

Ray: Regarding 3 versus 2, this is especially true for safety reasons.

The only low time I can think of was when I was with that skipper for 3 weeks, from Tahiti to Tonga. When we sailed into Bora Bora–a place I had been dreaming about my entire life–all I could think of was trying to figure out a way to get off that boat and let the skipper continue on without me. He was an awful person to me.

Aside from this, there were very few other low times. I loved every new passage, every new country, I enjoyed almost all of my shipmates and skippers. I learned things from all of them. I ended up being land-bound for 8 months in Malaysia. My skipper from Tonga to Malaysia lived there and invited me to stay at his house gratis until I found my next boat going west. I used his house–at his suggestion–as a home base while I took inexpensive flights to Cambodia, Thailand, and Indonesia for extended stays. I loved all 3 of those countries for different reasons. And having the luxury of coming back to Malaysia to relax and continue looking for my next boat was priceless.

Another high time was in St Helena where I was finally able to swim with Whale Sharks after looking for them for 20,000 miles.

I could list another twenty adventures I went on as high times. For me, this entire three-year trip was a mini-retirement, and I enjoyed almost the entire journey.

L.C.: By the way, your chapter on women’s avoiding sex creeps at sea generated a debate on one of the Facebook sailing groups where I had promoted the story. One guy commented that women looking to crew should refrain from posting pictures of themselves in fetching poses or skimpy outfits.

EXCERPT FROM ‘GLOBAL HITCHHIKING’

Advice to Female Crew Matt Ray   ·   Apr 1 Read full story

This prompted a woman commenter to go after him for blaming the victim, etc. It turned into a real Facebook shitfight. I have to admit, however, that over the years I have seen these kinds of photos, and they just left me shaking my head. No, these women don’t deserve to be assaulted, but I think this kind of pitch might be seen as an opportunity for pervy assholes. Weigh in, Matt. If you dare.

Ray: Agreed. Sometimes women like to have their cake and eat it too. I agree that women should be able to post whatever pics they want and still have our respect, but there are lots of guys who disagree. Which Facebook page is that? I’d like to follow along. I haven’t seen it in any of my groups.

You’ve even got a post on Substack which borders on the old argument that women shouldn’t be thinking that men are the enemy when planning to crew. Unfortunately, history has proven otherwise.

…Never mind, Detective Matt just found it in Sailing.

It looks like you like to stir up trouble in that group. Definitely get a lot of heated responses. That’s probably good for your Substack readership. I read through the comments on your solo sailing articles and many of them made me laugh. Is the clause about no solo sailing a universal thing with insurance companies?

I gotta be honest, after reading these articles I started wondering what I am going to do when I get my boat. Part of me wants to solo sail just to avoid the headaches of having someone else on board. I’ve experienced all kinds of drama and drama on a boat in the middle of nowhere is the worst.

L.C.: I think conventional wisdom needs to be challenged every once in a while. That’s for sure. Hence Loose Cannon, right? So, you’re thinking of owning rather than tagging along. What are your plans, professional and otherwise?

Ray: My original plan was straightforward: build experience, then move into professional sailing. Most likely that meant skippering week-long charters on a 40-foot catamaran or something similar. That was my introduction to sailing in the first place, and it’s why I chose to pursue the RYA Yachtmaster Certificate instead of a U.S. six-pack license. I wanted the option to work internationally, and the skipper on that first trip—a Brit—made it clear that the RYA certification carried more weight abroad.

The colorblind restriction was a complication, but not a dealbreaker. My plan was simple: Get experience, build credibility, and make the jump.

But somewhere out in the Indian Ocean, I started to rethink the whole thing.

Hosting paying guests week after week began to sound less like freedom and more like obligation. Realistically, some percentage of those trips would include people I wouldn’t choose to spend time with. Add alcohol to that mix, and it started to feel less like sailing and more like something I’d eventually resent.

Then I looked at the numbers. Delivery skippers often make around $100 a day. At the same time, I was earning $100–$150 an hour as a computer consultant. That contrast was hard to ignore.

At that point, the path became obvious. Instead of turning sailing into a job, I could keep it as something I actually loved. Go back to what I already knew, earn well, and use that to fund a boat of my own. These days, with tools like Starlink, working remotely from a boat isn’t just possible—it’s practical.

So, I let go of the idea of sailing for a living. The goal now is simpler: Own a boat, sail where I want, invite the people I choose, and keep my livelihood tied to something I’ve spent decades building.

Sailing stays what it was meant to be—not a job, but a life.