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Global Hitchhiking was published in July 2025, based on Matt Ray’s boatless circumnavigation from 2016-2019.
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.
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?
Sailing stays what it was meant to be—not a job, but a life.
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.
LOOSE CANNON covers hard news, technical issues and nautical history. Every so often he tries to be funny. Subscribe for free to support the work. If you’ve been reading for a while—and you like it—consider upgrading to paid.
Scheduled closure of the South Mills Lock for electrical repairs on April 20-22, 2026. Our thanks to Sarah Hill of the Dismal Swamp Welcome Center for this information.
Please see the USACE Norfolk District’s Notice to Navigation regarding the scheduled closure of the South Mills Lock on the Dismal Swamp Canal, April 20-22, 2026. This temporary closure is for electrical repairs to be made. The lock will reopen on April 23, 2026.
Attaching image from this week at the dock. Boaters are beginning to trickle through during this early springtime period.
Looking forward to many more in this season!
Thanks,
Sarah
Sarah Hill, TMP Director, Dismal Swamp Canal Welcome Center Chairperson, Camden County Tourism Development Authority 2356 US Hwy 17 North, South Mills, NC 27976
Bastardizing the American English language is really not my game; I tend to manipulate and over-describe rather than combine and shorten. But I couldn’t pull any terms out of my, um, repertoire, that described the situation any better than these shortcuts which frankly, get the point across damn well. I’ve had a British associate or two tell me we Americans bastardized a whole lot of their language anyway, so I figured, might as well keep on goin’…
And why, you may wonder, are such crude shortcuts in order? I arrived at STEADFAST’s substantial aft end last week and got quite a flashback. Or a couple of them, actually. The photo on the left was taken in September of 2024. The other one was taken this week. Sigh. Thought we were done? Looks pretty similar. Well, we mighta stripped that section last year. Mighta known it was gonna need it. Coulda, woulda, shoulda done something differently? No, not really.
The white hull on the left was the only section of the vessel that we were NOT going to refit….and now, we gotta.
The reality is that STEADFAST’s port side, (left facing the bow) is full-on southern exposure in a part of the northern hemisphere which gets some intense sun, in fact, three-quarters of the year it shines directly on those surfaces and, ironically, far less in the steaming summer months. Her near-century old planks (and some newer ones) didn’t stand a chance against Mother Nature’s solar array, nor did the caulking holding them together, even under half a dozen layers of enamel paint. Our very real concern is those materials cannot recover from so much sun and not enough sea; they need a fresh seal, re-caulking in maritime terms, which is quite a process. As often happens, our best protection from nature’s power wasn’t good enough, and over time her planks have dried and shrunk just enough to separate and be dangerous. Wooden boats are designed to be in the water to remain watertight— if the build is proper, the planks expand perfectly to squeeze the caulk, just enough but not too much, creating a seal. Click the story link below or peruse a (very) brief explanation as to what’s gotta happen next. THERE ARE NO SHORTCUTS.
We braced ourselves and dug in; there is no point in taking chances, compromising quality or cutting corners now. If you’ve been subscribed since the beginning of SPARRING (originally designed to be a wooden boat sailing and travel journal—you never know where life will take you…), feel free to skip to the next divider line or stay and get a refresh.
Many of you found STEADFAST after these crucial tasks were completed on the balance of the (above-water) hullsides. We also had to Caulk every inch of the 32 new planks on the bow, stem and knee. Somewhere I calculated that we completed all eight time-consuming, meticulous steps on approximately three-quarters of a mile, or 1650 meters of seam. Just today, we reefed, pounded and sealed 300+ on the starboard aft quarter seen above.
OK—the Caulking process; STEADFAST was extensively rebuilt in Puerto Rico in the 1980s by a very passionate and equally crazy Sailor who reads my words each week. His seal has lasted forty+ years and that’s impressive; some of this new work would not even need to be done if we hadn’t run into the lengthy rebuild which we are immersed in. After removing that old seam material (a process called reefing, another one of those maritime terms that has too many meanings, IMHO), the multi-step Caulking task consists of brushing on two protective coats of boiled linseed oil and turpentine in equal parts; my favorite boatbuilding aroma, seriously appealing to the forest lover in me, I suppose. After that tonic, some perfectly pounded fresh, soft, pure cotton strands (nothing man-made works as well), as many as three rows if the existing cannot be saved, are inserted and tucked firmly with iron and mallet. If I do say, we’re a hell of a lot more efficient at it than we used to be, but it was dejà vu like I’ve never experienced to be back to doing things I thought were completed months ago.
Then it is protected with red lead paint, from George Kirby Jr Paint Company in New Bedford, Massachusetts, where, coincidentally, a hundred and twenty years ago, William Hand Jr was designing beautiful, diverse boats, eventually reaching Design #608: our number, which can be found in the Massachusetts’ Institute of Technology archives. And Mr Hand still wasn’t even close to being done conjuring seagoing vessels.
When we first hauled out, July 2024, we had no idea what we were in for. OK, let’s rephrase. I had no idea what I was in for and the Sailor had a better idea but still no true grasp because STEADFAST’s problem was insidious. One of my favorite words, learned long ago from my treasured Grandma Pearl.
By early August, while experts were assessing the bow structure, I set about stripping her lovely transom, whose teak had been replaced in the 1980s rebuild. I also took at least a dozen coats off the highest of her hullsides, the steel gray color above that kick-ass bronze rubrail, stripping down to bare planks.
We had noticed and noted that some of the seams in that region had become just a little too loose for comfort. It was a tad disconcerting to see daylight out through one of the seams on the aft port side. Thinking we would simply take advantage of our four months or so out of the water prior to heading to the Bahamas in the fall of 2024, we naively thought we were killing two birds with one stone when in fact there was a giant flock to be addressed and managed. Unforeseeably giant. Ah, the best laid plans become those with no shortcuts.
One of the most stunning displays of power I have seen in a long time occurred here on April 1st. A very warm, windy day proceeded a slow-moving cold front with show-stopping lightning, wind and rain; as I write this two mornings later we are still socked in by fog, every surface dripping, unable to work on what needs to be done. Back to this appropriate expression:
They go awry, those plans, but I firmly believe that eventually things fall into place and happen as they should. STEADFAST and her crew found a place to call home for two years with a group of kind, kindred spirits the likes of which I have rarely encountered.
This week SPARRING WITH MOTHER NATURE enters its third year and I was inspired to look back on my first few pieces. They detail the devastation wreaked by Hurricane Dorian on Marsh Harbour, Abaco, Bahamas; the first is entitled IMPOSSIBLE TO IMAGINE. Those resilient individuals experienced a battle for life, not merely a spar, and STEADFAST was there, three years afterwards, listening to the stories and watching a painfully slow recovery. The balance of the pieces I produce are likewise stimulated by moments in time, characters and considerations. I find this platform and my reader interactions incredibly rewarding even if it is not monetarily so.
The name of this publication came to me in the spring of 2023 when we rounded Cape Hatteras in a considerable sea state, under full sail, and STEADFAST’s impressive rigging went slack. Even if you’re not a sailor you can intone how bad that might be, right? It was bone-chilling. Since masts are also known as SPARS, and we were in for remarkable jousts that summer and beyond which seem to have become contiguous, endless even, the title was born. It’s what all of us do every day, at least to some extent. That multi-faceted story was published in WoodenBoat Magazine (limited access) here. Mother Nature is the most predominant force on the planet and some humans think she can be conquered, tamed and harvested without harm nor foul. I don’t agree.
While SPARRING’s topics deviate, the fascinating, resource-consuming world of wooden boat construction and ownership has taught this mountain and desert dweller innumerable things. Not the least of which is patience. There’s no point in considering what Mighta Shoulda Coulda Woulda. The thing that matters is what ya gotta. ~J
See you here next week! Please restack this post so my community continues to reach water and nature lovers; we currently have subscribers from 36 nations. Along those lines, I am posting casual, imperfect, work-site videos on our YACHTING STEADFAST channel in order to document what has become a worthy, educational project.
Saving our piece of maritime history is a daunting task.
And more on Category 5 Hurricane Dorian, September 2019.
There is no greater natural force on earth than a Category 5 Hurricane. Dorian made landfall on the afternoon of September 1, 2019, at Elbow Cay, Abaco, Bahamas, and proceeded directly across the small but bustling city of Marsh Harbour; the utter destruction is still evident. In a never-before seen track, the storm struck with 185mph winds, rain and a …
Read full story
I so appreciate your support of my work. Have a wonderful week!
Cruisers Net publishes Loose Cannon articles with Captain Swanson’s permission in hopes that mariners with saltwater in their veins will subscribe. $7 per month or $56 for the year; you may cancel at any time.
This is a view of the Caribbean Safety and Security Net’s interactive crime reporting feature on its website.
Caribbean crime reports declined last year, but suddenly Panama emerged as a hotspot for theft in its anchorages, according to the Caribbean Safety & Security Net.
In its recently released report for 2025, the crime reporting organization also noted that incidents in the British Virgin Islands appear to have declined dramatically. And violent crime in general dropped slightly, down to seven reports from eight in 2024.
From the CSSN summary:
In 2025, reported incidents of crimes against yachts in the Caribbean totaled 124, a 14 percent decrease from the record high of 145 incidents reported in 2024. This moderation follows a year of unprecedented activity and signals a return toward the five-year average of 119 incidents. Violent crimes continued their encouraging decline, falling to seven incidents (from eight in 2024).
Geographic concentration was a defining characteristic of 2025. On a positive note, the British Virgin Islands (BVI) saw a dramatic decline from 20 incidents to four.
Offsetting this improvement, Panama emerged as the most active country in the region, with all-time region-wide record high activity of 33 reports, a 200 percent increase from 11 in 2024. Activity in Panama was concentrated in the Bocas del Toro archipelago, and the Linton Bay area.
Activity in French Saint Martin increased modestly (from 13 to 15 incidents), remaining elevated; however, the nature of the activity shifted. St. Vincent and the Grenadines trended upward (from seven to 12 incidents) as cruising patterns normalized during the continued recovery from Hurricane Beryl.
In July 2025, three West Indian men received long sentences in connection with the murder of an American couple the year before, one of the most heinous crimes against foreign cruisers in recent memory. Ralph Hendry and Kathy Brandel of Fairfax, Virginia, were killed after the trio boarded their catamaran off Grand Anse Beach on Grenada in February 2024.
Panama’s government last year recognized the problem of outboard motor theft when it instituted harsher penalties for the crime. The penal code was amended to impose a prison sentence of six to eight years for the stealing motors valued over $250. The penalty also applies to those who anyone who deals in stolen motors.
The Bocas Del Toro cruisers page on Facebook contains the same type of advice heard through out the Lesser Antilles about securing dinghies and outboards at night and not leaving valuable items on deck.
If you area foreign cruiser in Panama waters, and you have some insight on the problem, please leave a comment below.
LOOSE CANNON covers hard news, technical issues and nautical history. Every so often he tries to be funny. Subscribe for free to support the work. If you’ve been reading for a while—and you like it—consider upgrading to paid.
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