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.

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.

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.

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.

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.