I sat back, sipping my Oceans Bourbon, while an episode of Sailing Fair Isle played on the screen. I was watching closely, hoping to catch a glimpse of my sons, who were on a catamaran somewhere in the background while Steve and Judy filmed their latest adventures in the ABC Islands. My email pinged. Glancing at it, I saw a YouTube VIP announcement for the Annapolis Sailboat Show. It came from a friend, Jeff Bach, whom I’ve known for the past few years, who was hosting an all-access pass for a lucky group of people. The package promised full access to all the YouTuber events. What does that even mean? I wondered.
The Sailing YouTube community is a unique genre unto itself. This is a niche, with around 4 billion video views spread across more than forty thousand videos and a subscriber base somewhere between 250,000 and 400,000 people. To put it in perspective, there are only about 1.7 million sailboats registered in the entire U.S.—less than 1% of all boats. And of those sailboats, many are skiffs, car toppers, or trailer sailers, not the bluewater cruisers these channels focus on. 95% of all U.S. boats are towable motorboats. So these cruising channels, where liveaboards are documenting life on the water, are a kind of unicorn in the boating world.
October in Annapolis brings everything to a head. Five key forces converge in this historic Maryland town during the annual Annapolis Sailboat Show. First, the boats themselves—new models that will either make or break the builders’ year. Second, the vendors, whose sales during this event often make up a massive portion of their yearly revenue. Third, the cruise and charter companies, who lure unsuspecting newbies into fractional yacht ownership with the promise of a dream vacation. Fourth, the social events, hosted by manufacturers for new buyers and current owners. And finally, the piece that catches my eye—YouTube creators and the fan meetups that now have a strong presence at the show.
The industrious Jeff Bach started the YouTuber tent about four years ago. It’s a spot where fans can meet their favorite creators in person. We’ve been going to the Annapolis Sailboat show for 14 or so years. I am sometimes doubling down and attending the Spring show too. As a YouTube aficionado and a longtime supporter of this genre, I’ve watched this idea grow into something more significant each year. Now, other boat shows have started creating spaces for podcasts, YouTube creators, and content creators. I’ve supported dozens of channels over the years, and though I’ve trimmed that back a bit since retiring, I still follow and help a few. Cruisers help cruisers—it’s in the blood—and I see value in the way these creators bring this niche lifestyle to a broader audience.
Because make no mistake: cruising isn’t a sport. It’s a lifestyle, one that encompasses everything from free diving and surfing to long ocean passages and life at anchor. As a former boat kid and current full-time cruiser myself, I sometimes wonder if this community will continue to grow post-pandemic, or if we’ll see it shrink again. Either way, I want to help normalize and de-stigmatize the cruising life. And supporting the creators who document it is one way to do that.
So I clicked “Buy” on the VIP tickets, securing my spot at the show and access to all the YouTube creators. It felt like a smart move—until a hurricane came calling, and I had to make a fast decision to protect my home. We had already secured Eoti for bad weather, but the timing was tight, and there was no choice but to head back south. We’d left just after Hurricane Helene and ahead of Milton, who was projected to come barreling toward Florida.
Watching the storm from Washington, D.C., I realized I couldn’t risk it. I popped smoke and headed back down to Florida, opting for the old Volvo rather than air travel. It was a long, lonely drive straight into what might’ve been the teeth of a Category Five hurricane. By the time I arrived, I was wrecked, but there was no time to rest. I prepared Eoti—took some pictures, turned on the security systems, alerted my neighbors, and then headed back north to rejoin my crew.
Some folks might say, “You could’ve stayed.” Or, “You should’ve done something different.” And to those people, I say: keep your gabby mouths shut. The couch-bound crunchy commentariat, sitting there without boat, clue, or understanding, should sit this one out. This life isn’t for them, and I’m not trying to explain it to someone who doesn’t get it.
But Eoti was safe, and I made it back to Annapolis just in time for the show. Exhausted but there. Jeff Bach had events lined up every night—VIP parties, creator meetups, and more. At one of these, some young YouTubers shot me skeptical glances. But old friends, people from the community who’d known me for years, came up and gave me big hugs. They knew me, knew my wife, and welcomed us warmly. The younger crowd didn’t quite know what to make of a guy like me—a face made for radio, not YouTube.
I’m not much for mingling or “working the room” at parties. That’s for the young, for people who have the energy. Me? I find a comfortable spot, grab a beer, and let the party come to me. I’m not interested in playing “touch the star.” I’ve lived a life full of enough stories and experiences to satisfy any room, but I know for the creators at these events, it’s often just another day of work. And that work is grueling—soul-searing, even. Being “up” and “on” all the time is tough, and I respect them for it. My way is quieter. I like to ask the questions others don’t, and if they’re game, I’ll tell the stories they’ve never heard.
After all, I’ve got titles most people can’t dream of: author, captain, cop, executive, marine, motorcyclist, professor, soldier, spy, vagabond—you name it, I’ve done it.
Each day in Annapolis was spent talking to vendors and attending presentations. Each evening was spent with the creators I’ve followed and supported over the years. Sailing Fair Isle, Spirit Animal, Delos, Harbors Unknown, Heidi and Franny, David Shih Sailing, Sailing One Life, Sailing Doodles, Parlay Revival, Ryan and Sophie, Rigging Doctor, and so many more. I even met some new channels—like The Spoon Drifters and Sailing Pickles. We talked about everything from YouTube metrics to content strategy, and I shared a bit of my own background in scientific data analysis. Some agreed, some didn’t, but hey, it’s all free advice—take it or leave it.
By the end of the weekend, I was reflecting on some of the highlights. Like racing with Delos against Parlay Revival aboard the Woodwind schooners, or grabbing random hugs from fellow cruisers I’d met at the show. I’m not a social butterfly, but I get a thrill from seeing so many cruisers. People like Liahona, Sailing Rome, and Sailing La Vida Gypsea—they’re living the life, but not always front and center at the creator events.
The show was also bittersweet. The iconic Pusser’s Painkiller—a fixture of Annapolis for decades—was fading into history, and many of us drank our “last” Pussers at the show, knowing its future at Annapolis ended with this show.
VIP tickets aren’t cheap, but they were worth every penny this year. From the Annual Cruisers Awards (where Sailing Fair Isle won Best YouTube Episode and Spirit Animal took home Channel of the Year) to Rafael proposing to Sascha in the middle of the ceremony with a diamond ring—it was a year of unforgettable moments. And next year, I think Eoti deserves a spot right out front, sitting pretty in the bay for all to see.
Because, like most things, you get out of it what you put in. This year, I put in the miles, the time, and the bourbon. And I got a hell of a good time in return, thanks to Jeff Bach’s little VIP idea. Cheers to next year.