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.

We’ve said it before, and we’ll say it again: we didn’t win the lottery and we aren’t trust-fund babies. We don’t have an endless pot of money funding our cruising lifestyle. We didn’t wait until we were retired with a solid nest egg either. Instead, we work, we tackle projects on our boat ourselves, and we’re always looking for ways to save money. Cruising can be expensive, but if you’re cruising on a budget, it’s absolutely doable. You just need to get creative.

The original plan was simple: stop for the 2024 total solar eclipse in Mazatlán, then head deeper into the Sea of Cortez for the summer. But as cruising often goes, plans change. What was meant to be a quick pause turned into three weeks of exploring the city, soaking up the local culture, and even becoming official temporary residents of Mexico.

Electric winches? Yes please! Glossy wood interiors? Oh Yeah! Fancy electronics? Must have! And just like that, we were looking at boats that were bigger, fancier, and way out of our budget.

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.

Our plan: drop the stern, motor forward, drop the bow, and snug everything tight. Reality: wrap the stern line on the prop, drift awkwardly across the anchorage, and scramble to recover.

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.

The bar crossing at Bahia del Sol is legendary among cruisers. Reactions range from “the most fun thing I’ve done on the boat” to “You’re crazy. You’ll lose the boat.” And yes, a boat was lost at the bar recently. Since then, new safety regulations have been put in place, and local pilot boats guide vessels across. Still, it’s a surfy ride. One you have to commit to.

When we first started preparing for full-time cruising, we had no idea what we actually needed. YouTube made it look easy—just buy a boat, slap a solar panel on it, and go. Meanwhile, every sailing forum, association, and outfitting list told us we’d need ten pages of gear and a marina-sized budget. Somewhere between “a dream and a dollar” and “you need three backup autopilots and will die without a windvane” lies the sweet spot.

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.

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.

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.