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.

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.

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.