What it’s like when you’re alone in a tiny boat for weeks.

In What It’s Like, people tell us, well, what it’s like to have experiences many

In What It’s Like, people tell us, well, what it’s like to have experiences many of us have not even imagined. In this entry, we spoke to amateur mariner Sam Holmes, 35, who crosses oceans—by himself—in a dinky sailboat. Holmes is from North Carolina, and previously worked at Disney as an Imagineer. Now he spends weeks of his life at sea, documenting the trials and tribulations of a lonesome skipper for his 230,000 YouTube subscribers.

I first learned how to sail as a teenager. It was just a summer camp activity, something I did for fun. When I was in my early 20s I purchased my first boat for myself, and I found a blog of someone who sailed around the world on a catamaran, and that’s when I learned it was possible to basically live on the sea, rent-free. The cogs started turning in my head; maybe this was something I could do much later in life, maybe after I retired? But I kept thinking about the idea, and in my early 30s, I decided to give it a shot. I charted a route from Los Angeles to Hawaii following the trade winds, which seemed like an easy introduction to long-distance sailing. The whole trip took 27 days, and my vessel was 23 feet long. That’s how it all started.

I wasn’t sure how the trip was going to go. There was a chance I’d cross the Pacific Ocean and decide that I hated being isolated for weeks. Or maybe I’d get to Hawaii and decide to sell my boat. But everything went so perfectly on the trip, which was a surprise, because I didn’t really know what I was doing. Honestly, I wasn’t even sure if I was going to make it, as I had a lot less sailing experience than other people at the time. I didn’t think I was going to die or anything—if I thought that was a likely possibility, I wouldn’t have done it. But it goes without saying that there are a lot of ways to get killed when you’re alone on a tiny sailboat in the middle of the ocean. You could fall off the boat, or it could catch fire, or it could sink. The vessel was 40 years old at the time of the voyage—things could have definitely gone wrong.

Once I arrived safely, I put up a video documenting the trip on YouTube, which got a really positive response—almost 5 million views in total—and it seemed like a sign to keep it going. I’m now making more from YouTube than I did at Disney, which is nuts. These days, I spend much of my life either in port or on the ocean. When I first started sailing full time, I would be out at sea through spring and summer, and fly back to America for autumn and winter. But going forward, I’m thinking about sailing throughout the entire year. Everyone in my life has been supportive of me, though my mom does get a little nervous. I do keep a workshop back in my native North Carolina. It’s an old gas station that I was able to buy for only $15,000. That’s my home base. I think that’s my favorite part of this lifestyle, drifting from cool anchorage to cool anchorage, seeing whatever I want to see. I’m in Greece right now, which is beautiful, and I’ve been exploring the Mediterranean lately, which I’ve been meaning to do for the last two seasons. It’s cool to look back and see all the miles I’ve traveled. I’ve sailed as many as 6,000 miles in a year. When I’m out in the water, staring up at the stars, without a boss telling me what to do, that’s the good life.

There aren’t many people who sail long distances alone. I’ve met maybe a dozen other people who do this, and many of them are from the connections I’ve made on my YouTube channel. For the most part, sailors don’t especially want to spend a month by themselves in the ocean. But personally, I find it practical. If you really want to do something—and you’re going solo—then nobody can back out, or ruin your plans. Everyone seems excited about a big sailing trip at the beginning when it’s a speculative idea, but they don’t always come through. For whatever reason, I don’t get lonely during a long trip. I tend to be a bit more social once I get into port, when I’m around other human beings for the first time in weeks. But that’s it.

Much of the time, sailing by yourself can be a pretty sedate experience, but it does get scary when the weather turns, when the wind starts howling, and the waves pick up. It becomes hard to manage. Every little mistake you make out there compounds into each other. It’s especially scary if I’m in bad weather after a break from sailing, and I’m not on my game while captaining the ship. The worst squall I ever endured was off the coast of Ireland, with wind gusts sustaining up to 30 knots and waves up to 15 feet—so, almost the size of the boat. They just slammed into the hull. But honestly, the most frustrating part of traveling this way is dealing with all the visa issues at different countries when you come into port. [Ed. note: In one video, Holmes documents how he was forced to remain in isolation before taking a COVID test in Faial, Azores, despite the fact that he had traveled to the island by himself after a 23-day voyage.] The man-made problems end up being the most frustrating.

When I’m on a voyage, I can usually count on seeing another boat in the ocean once every two to three days or so. Shipping containers and tankers pass by, on the horizon. I also have AIS [Automatic identification system for ships, which alerts mariners to nearby vessels], so I’m able to detect far more ships than I would otherwise. If I’m ever in trouble, I know I can probably find some help. In the meantime, I’ve got a ton more sailing achievements left on my bucket list. I’d love to circumnavigate, or do Cape Horn and the South Pacific. Lately I’ve been looking into Antarctica. The world is your oyster.