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.

When we decided, without much research, to sail into El Salvador and spend the summer, we didn’t know much about the place. This tiny country wedged into Central America is generally overlooked because of its violent past. Undaunted, we crossed the notorious bar entrance into a country that was entirely new to us.

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.

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.

When we tell people we live full-time on a sailboat in the tropics, most assume we’re either retired or sitting on a hefty trust fund. Truth? We’re neither. We’re just two regular people who decided that time was more valuable than stuff—and figured out how to make money sailing so we could keep doing what we love.

A lot of people think of sailboats as wind-powered machines—and they are. Yes, there’s a handful of engine-less sailors. But for the majority, chances are, the diesel engine is the go-to for docking, tight anchoring situations, and emergencies. If that engine dies at the wrong time, it can put a boat (and the crew) in a tricky situation.

When we first decided to “sell it all and sail away,” we had no experience. No boat. No plan. No idea what we were doing. Our only time on the water had been in canoes, kayaks, and the occasional fishing trip. Sailing full-time sounded like a cool way to explore the world with our home, and dogs, in tow—but we had to figure it out from the ground up.

We signed up for sailing lessons—but Covid had other plans. So we did what any desperate dreamers would do: we bought a sailboat off Craigslist, with no experience. Yes, really.

British Columbia’s Sunshine Coast and Gulf Islands offer some of the most underrated sailing anchorages on the Pacific Coast. While many cruising guides highlight dramatic destinations like the west coast of Vancouver Island or the glacier-fed inlets of Alaska, savvy boaters know there’s something special about these more sheltered local waters.