5 Things We’d Do Differently Before Moving Onto a Sailboat Full-Time

We got the genius idea to go sailing after a sneaky trip to Mexico in 2020. One boat off Craigslist, a crash course in sailing (kind of), and then another boat later… and we were off. Needless to say, we jumped in with both feet.

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.

Here’s what we’d change, in no particular order.

We’d Take More Time to Downsize Before Moving Onto a Sailboat Full-Time

No fire sale. Get a storage locker. Or don’t. It depends on your circumstances.

When we bought Raicilla, we also decided to sell our apartment and move aboard. We knew we’d be leaving for cruising in a year or two, so it made sense. The apartment sold much faster than we expected, and suddenly we were on the clock.

We had three months to clear everything out and fit our lives into 40 feet. On paper, no problem. In reality, it was messy and stressful.

We didn’t know what to bring, what to sell, or what we might regret letting go. With the deadline looming, we rushed through it. That meant selling things far cheaper than we wanted—or giving them away—just to get them out of the apartment. And we ended up with a boat full of items we didn’t really need.

Looking back, we should have rented a storage locker from the beginning. We could have sold the big-ticket items at our own pace and left the smaller “maybe” items for later. Instead, we burned ourselves out with a fire sale and spent our first months aboard tripping over excess stuff.

Ironically, six months later we did get a storage locker. It was a blessing—it gave us breathing room on the boat and more time to sort through what we wanted to keep before leaving Vancouver permanently. By the time we sailed south, our possessions were down to what we could carry and a couple of boxes tucked into our parents’ basements.

If you’re making the leap, give yourself more time than you think you’ll need. Downsizing is its own emotional journey.

Finally cleared out the apartment.

Why a Better Dinghy Matters When You Live Aboard

Our boat came with an eight-foot inflatable RIB and a 6hp motor. We replaced the motor pretty quickly, it just wasn’t powerful enough, but we naively assumed the dinghy was “good enough.”

In British Columbia, it kind of was. Dinghy wheels weren’t common, and most landings were docks or rocky shores. The little inflatable shuttled us around just fine.

Then we sailed south. Cue the reality check.

Our dinghy is now patched, scraped, and limping along on cheap wheels that have fallen off a couple of times. And every time we drag it up a beach in Mexico or El Salvador, we kick ourselves for not buying a sturdier, slightly larger dinghy while we still had steady income and access to gear in Canada or the U.S. Importing a new one now is both expensive and complicated.

There’s no such thing as the “perfect” dinghy—some cruisers swear by the OC Tender, but at well over $10,000, it wasn’t in our budget. Still, we wish we’d invested in something durable and dependable when it was easier. Now deep in the mangroves of El Salvador, we’ve just come up with a solution to our dinghy woes (stay tuned).

If you’re preparing to cruise, don’t underestimate how important your dinghy will be. It’s not just your tender, it’s your car, your pickup truck, your lifeline to shore. Get the good one, with proper wheels. You won’t regret it.

Thankful for friend who come to the rescue of a broken down dinghy.

Embracing the Learning Curve (Not Perfection) as New Cruisers

When we first started out, we joined sailing associations and groups that made us feel like we needed to have the perfect boat, perfect systems, and perfect seamanship before heading out. The members taught us so much, and we’re grateful. But we also carried around constant anxiety that we weren’t good enough.

Then we sailed to Mexico. And the truth hit: some of the happiest cruisers out here are sailing boats held together with duct tape. Everyone is figuring it out as they go.

Our dinghy is currently lashed together with glue and ropes. We once helped a woman with zero experience dock her newly purchased boat in a tricky marina. Perfection is an illusion. Resourcefulness is what keeps you afloat.

Looking back, we wish we’d worried less. Yes, we still have money stress and boat projects, but cruising teaches you to get creative and solve problems on the fly. The learning curve is part of the adventure.

If you’re waiting for everything to be “perfect,” stop. You’ll never leave the dock.

Making Strategic Boat Upgrades for Full-Time Sailing

While we lived on the dock, life felt easy: unlimited shore power, unlimited water. We knew we’d eventually need to think differently, but we didn’t practice.

Once we left, power management became our biggest headache. Our original solar and wind setup wasn’t enough to keep us going. We refused to get a generator at the time and instead installed a high-output alternator. It worked, but two years later we hardly use it—it overheats the boat at anchor and takes away precious horsepower underway (also it’s a sailboat - we sail more than motor).

What we really needed was more solar. Eventually, we doubled our array and added a small portable generator for cloudy weeks or when we need air conditioning (like every single day of summer here in El Salvador). That combination has been far better.

The lesson? Don’t just buy gear because someone says it’s essential. Think about how you will live aboard and make upgrades strategically.

Installing the now useless alternator.

Building a Better Income Plan for Life Afloat

When we first cast off, we wanted a break. We weren’t interested in working, so for the first year we lived off savings and enjoyed the freedom.

The trouble came when it was time to re-enter the world of work. We assumed it would be easy to pick up freelance projects when we needed them. It wasn’t quite that simple. Fortunately, we had a strong network (and a bit of luck), and eventually the writing and consulting work flowed. But there was a stressful gap before it clicked.

In hindsight, we would have set up small income streams before leaving. Not full-time jobs, but enough to give us confidence during that first year without tapping savings too fast. We also would have invested more aggressively before casting off.

Cruising is cheaper than many people think, but it’s not free. Having a plan for income—whether it’s freelance work, investments, or seasonal gigs—makes the journey much smoother.

Hard at work, or hardly working?

Conclusion: You’ll Still Make Mistakes—And That’s Okay

No matter how much you plan, things go sideways. As I write this, I’ve got a block of ice wedged into the fridge because it quit cooling last night, and Mark is nursing a stubbed toe that bent so badly it went sideways (we’ll spare you the photo).

But the bigger picture? None of it matters. We’re here, sailing, living a life that’s ours.

If you’re dreaming of going from landlocked to liveaboard, take these lessons for what they are: hindsight, not regrets. You’ll make your own mistakes, too—and that’s part of the adventure.