There’s a strange comfort in boatyard life—everyone’s a little tired, a little broke, and a little sunburned. But we’re all in it together, trading tips, tools, and beers. It’s the kind of shared misery that somehow turns into great memories later.

Sell it all. Move onto a sailboat. Live for free. Sounds simple, right? When we sold everything and moved aboard, we knew it would be cheaper than renting an apartment in one of Canada’s most expensive cities. And when we set sail for full-time cruising, we figured the costs would drop even further.

The climb involved scaling narrow rock cracks and trusting frayed ropes that looked like they’d been installed sometime during the Steinbeck expedition itself. We got stuck, got scratched, but made it to the top. And, more importantly, back down alive.

Would we run out of money? Would we die at sea? Would we feel lonely? Would the boat constantly break? Would we regret the decision altogether? Now, after years of sailing full-time, here’s the reality behind those fears.

Then there’s time. Everything takes longer. Groceries can take a full day. Checking into a country? Hours of paperwork and waiting. Boat projects stretch on indefinitely, often with a little bloodshed along the way.

Fuel concerns returned. With only one jerry can left, the next refuel points were La Paz or Puerto Escondido. La Paz was logical, but we preferred to avoid it.

I’d be lying if I said our sailboat adventures were only about the destinations. A huge part of cruising life is the time spent underway. Those hours and days when we’re keeping the boat moving toward the next port. But what exactly do we do while we’re out there? Especially on longer passages that stretch beyond a few hours and turn into days at sea? Great question. Let me take you along.

Now, three years later, sitting in a river in El Salvador waiting out hurricane season, we’re reflecting back on the things we probably would have done differently. Not regrets. We’re full-steam-ahead kind of people. More of a list of five lessons we’d approach differently if we had the chance to do it again.

No, we didn’t win the lottery. We don’t have a secret trust fund. And despite the tropical backdrops, this cruising life didn’t just fall into our laps. We work. A lot of other younger cruisers we’ve met work too. Often between snorkel trips, surfing and sail changes there’s a laptop open. It might not be the glamorous “quit everything and drift into the sunset” life we imagined when we left Vancouver two years ago

We’ve been in El Salvador for over three months now. And we’re still here. Why? Because slow travel by sailboat often means waiting for the right time, and right now isn’t it. To the north, it’s hurricane season. To the south, it’s stormy season. And to top it off, the ocean swell is too big for us to safely cross the bar and head out into the Pacific Ocean.

Of course, that short trip came with drama. What started as a calm sail quickly turned into a full-on retrieval mission when our dinghy wheels went overboard. Of course, the wind decided to ramp up to 25 knots just as we tried to fish them out. Yes, we had all the sails up. After 45 frantic minutes, we managed to retrieve the wheels—along with the realization that if either of us ever goes overboard, we’re probably not getting rescued.

Late-night goat calls, chonky feral sheep, and an abandoned homestead. Jedediah Island is one of those remote anchorages in BC that feels like it exists outside of time. For anyone cruising the BC coast, it’s an unforgettable stop.

When we first talked about buying a sailboat and traveling full-time, people often assumed it would be a cheap way to live. And, honestly, so did we. But the real answer to “Is it cheaper to live on a boat?” is: it depends.