What They Don’t Tell You About Living On a Sailboat

Back when the pandemic was new and I had been freshly evacuated from a tropical island where I had been living since 2017, I got bored. Not because everything was closed, or because I was stuck inside all day. I was quite used to not being able to go out and about – no, I was bored because life for me had just gotten a whole lot easier. I was eating square meals, had potable water, and could safely exercise without fear of heat stroke or sexual harassment. Are my standards for a good life low? Maybe.

About a month into being back in my cushy American life, I found myself craving a more engaging life. I felt disconnected from the whims of nature and wanted to build a more sustainable lifestyle. Some made sourdough, some made masks… I decided to live on a boat. Within ten days of deciding this, my husband and I checked out a bunch of boats on Craigslist, drove many many miles in the American Northeast, and bought a little 30 foot sailboat from 1974.

Hello, April in East Boston. How cold art thou? Too f’ing cold.

Immediately after buying our dear Flingo Bingo (yes, that is the sailboat’s name), we sailed off into the sunset and it has been smiles and champagne ever since.

Just kidding! While land dwellers associate boat life with romance and adventure (there is definitely plenty of both), living on a boat comes with its own set of challenges. I find this life fun, and I am always learning something new about things I never even knew existed. Here are just a few things that people don’t tell you about sailboat living.

You don’t have to be rich to own a boat.

Maybe this is obvious to some, but every time we say we live on a boat, people assume we have a lot of money lying around. We simply don’t. The beauty of living on a boat is that you can be as excessive or penny pinching as you want – it all depends on your income and how much money you like to spend.

We live on a humble 30 foot, incredible-to-sail, fifty year old boat. It cost less than buying a used car in the United States. Because it is small and doesn’t have a lot of fancy electronic systems, maintenance is quite affordable. If we wanted, we could do really expensive refitting jobs to make the boat more modern, but we are pretty minimal in our needs of a living space.

So, yes, you could buy a million dollar yacht. But you can also find a sturdy, well-cared for boat and ride the waves just as well.

Leaks are the bane of my existence.

Just as land dwellers are constantly battling things like drafty windows, we are constantly finding new leaks in our boat! No, not the sinking kind, but the annoying kind that soaks your mattress and creates small puddles on the floor.

Our boat is actually a lot drier than many others, but inevitably, with every bout of rain, we are always just a bit disgruntled to find yet another leak on board. More leaks = more mold = more cleaning to prevent mold from taking over my little home. We have learned a lot about sealing windows and cracks and more, which is kind of cool right? Right.

We are less like Moana, and more like Heihei.

I’ll be honest, both the hubby and I really love Moana – the music, the spirit of adventure, the story. In order to make it through tougher sailing days, we would play the movie soundtrack and pretend we were just as brave as a 14 year old kid crossing the ocean by herself. And while I like to think of myself as similar to Moana, the reality is I end up more like Heihei (but only because I don’t have much boating experience and I am a bad swimmer?!).

Heihei is my true self. Sometimes.

While life on a boat (and cruising around here and there) is definitely fun, we have learned the hard and scary way that Mother Nature will always win. It is totally humbling, and you never stop learning about life on the water.

Boat people are (generally) the most generous and helpful people you will meet.

I think this comes from a strong sense of camaraderie and shared level of weird/crazy in terms of personalities. Boat people – the ones who live on their boats, the ones who just boat on weekends, the ones who work in marinas and other parts of the industry – are by far the BEST. We have had people spend several days helping us secure our boat during a tropical storm, give us serious discounts for staying in marinas to evade bad weather, total strangers lend us tools and help with engine issues, and more.

If you find yourself in the presence of a boat person, soak in the good vibes and general kindness. All boaters have experienced the best and the worst that boat life has to offer, so we know how hard (and how good) life can be. Being there for each other is not only nice, but necessary.


I could go on and on about the unexpected realities of life on a sailboat – I will definitely write more about it in the future. For now, I hope this gives you a taste of what I certainly didn’t expect going into this lifestyle. Cheers!

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