Once upon a time my house was 27 feet long and 9 feet wide, space was tight. Amenities minimal. When our daily lives weren’t frustrating, they were hilarious. Progressive insurance got a kick out of this and asked me to answer some of my most common questions. One of them being – What was the best, and the worst part about living and traveling aboard a 27 foot sailboat for two years? 

best & worst -10.jpg(ABOVE: How to stay warm in Canada)

So I present you… the glitter and the shits.

I began writing a simple list: The best things about living aboard a tiny sailboat. I shocked myself with the amount of bullet points that dotted this category. It was as if they had been pent up in my brain waiting to be released onto paper. I then began my second list: The worst things about living aboard a tiny sailboat. My brain fired again, and the bullets struck the exact same points as the first.

Every reason that was the best was also the worst. My lists were nearly a perfect match. Contradicting? Well, kind of, yes, let me explain:


Simplicity // You have with you one of everything you need and nothing more. You have left all the clutter behind. Your diet is simple. Your wardrobe is slim. You might have two pairs of shoes, if you haven’t lost one overboard. You sleep when the sun goes down, and you awake when it rises. You stop paying attention to time, calendars and all of numbers that once defined you. When you have no Internet, you read a book, and when your phone dies, you write letters. You perfect the art of sitting still. You find joy in the simplest of things.

Take your home anywhere // The longer you live aboard the boat, the more foreign a square house in a cement neighborhood begins to feel. This vessel becomes your home, your safety zone, your friend, your transportation and your ticket to explore the world. Restrictions are slim, and opportunities are endless.

Jack of all trades // You get to try on a lot of different hats. When something breaks, you take the time to figure it out on your own before making a phone call. When you are on a tight budget with plenty of time, you will be amazed at what you are capable of fixing, much the opposite of those who have a plentiful budget and are tight on time. You suddenly find yourself to be a bit of a mechanic, plumber, electrician, craftsman, sailor and a navigator. At this point you lose your mind a bit and start to think you are really funny, this is the best part.

Mother Nature // As you can imagine, this reason is self-explanatory. Sunrises. Sunsets. Harvest moons. Wildlife. Eagles. Pelicans. Herons. Otters. Dolphins. Alligators. Manatees. Sharks. Spiders. The brightest of stars. Incredible cloud formations. Thrilling thunderstorms. Blinding rain. Flowing rivers. Fresh water lakes. Vast salty oceans. Ever changing scenery. It never gets old.

Uncertainty // Every day your goal is to get from point A to point B. You don’t really ever know if you are going to make it. In my opinion, there is nothing more thrilling nor motivating than a good challenge. There is a perpetual flood of unanswered questions, and you are constantly educating yourself simply by being curious.

best & worst -3(ABOVE: How to fit into the v-berth with all your crap)



Simplicity // When it rains, you get wet. When it’s unbearably hot, there is no air conditioner. When the deck frosts over, you have no source of heat. When all of your clothes are dirty, you have no laundry. When you are starving, you open a can of tuna with a side of brown avocado. When you are filthy, you jump in a salty ocean or a muddy river for a bath. When the sun goes down, you turn on your headlamp. Above all else, there is sometimes never-ending physical discomfort.

Take your home anywhere // Once you are used to constantly being on the go, it is very, very difficult to flip that switch off. You are never settled. It’s hard to stay at a job. It’s hard to stay in a relationship. It’s hard to stay in one place—period—knowing you can untie the lines at any time you please. The ability to move your home trumps everything. So you go, and you keep going, and you are constantly saying goodbye.

Jack of all trades // When your engine quits, you will sit in front of it for countless hours praying that your intense stare will fix the problem. When you can’t fix the engine, you become the sailor who sails in every direction besides the right one. When your head breaks, you are the plumber. When salt corrodes your electric wires, you are the questionable electrician. When you are lost, you are still the navigator. The dirty jobs cannot be pawned off to highly-qualified tradesmen.

Mother Nature // There is no negotiating with Mother Nature. Quite frankly, she couldn’t care less about you and your needs. She will change her mind at any moment, day or night, forcing you to alter your route, take shelter or ride it out. You are always at her mercy. She is your mother-in-law who you secretly despise. You are nothing but a game piece on her game board while she deviously deals the cards.

Uncertainty // Again, you are never certain if you are going to make it to where you are trying to go. The variables and obstacles that could be chucked at you throughout your daily travels will keep coming, but you will never know when. Having to re-route, seek out plan C or backtrack is common. Nothing is certain. Even when you have firm plans, you must understand that things may not go accordingly.

You see what I am saying? It is merely a matter of perspective. If your glass is half full, you understand list one and might consider this a lifestyle for you. If your glass is half empty, list two is enough to make you cringe every time you see a sailboat hereafter. List one wins in my opinion, and if list two hits home for you you probably shouldn’t live on a boat and I apologize that you just read this whole article.

best & worst -1(ABOVE: How to shower in your living room)

C-O Canada -19(How to successfully beg for food)

Life-Lanes-1(How to successfully be a bed hog)

best & worst -7(How to pretend you are going faster than 4.5 knots)

best & worst -11(How to park your house)

best & worst -12(How to … live)

Disclosure: I was compensated for content provided to Life Lanes from Progressive. All thoughts and opinions are my own.

30 thoughts on “The best bits…&…the worst bits

  1. Good to see your sweet writing back online. A terrific book lies within waiting to be released- no doubt. And more adventures to come…

  2. Soooo, what’s this I saw in an Instagram post from the Annapolis boat show about a Catamaran?! and the Bahamas?!!

  3. Once again, really enjoyed reading your blog. Insightful and refreshing. Not just another euro-trash pretty girl asking for $. Keep up the good work ! Cheers !

  4. I’m having boat withdrawals. For temporary relief I am following ‘Trio Travels’ on youtube–they are living aboard a Fountaine Pajot sailing cat in the Bahamas; I recommend giving it a watch. I hope to be able to add your cat/Bahamas travels to my watch list soon.

  5. Why is it I always think of Captain Ron when I read your post?

    Captain Ron: Alright, that’s more like it, now you’re talking! You can do it, mates! I’ve never seen such sailors. Not in all my born days, I ain’t. Naturals! My God, everyone of you, naturals…

    Captain Ron: We’re gonna fucking die!

    Love Ya’!,
    Uncle Milt

      1. As a matter of fact, I do! Your video should be used in a “Diesel Engine Troubleshooting” seminar.

  6. Hey, where’d you put the litter box for kitty? I’m still trying to figure out that little iota for my cruise.

  7. We heard you speak about your trip last summer at Charlevoix, MI. Enjoyed listening to your adventures and all your great pictures of your trip!

  8. I miss sailing so much, sitting here chained to a desk and a life I love (but doesn’t have room for sailing – not like you do it!) Anyway, this page brought joy to my soul. You chose one path, I chose the other. We both made it work, but remain fully aware of the tradeoffs. I hope you never lose your sense of adventure, yet someday know the contentment of being permanently moored. Enjoy this season while it lasts, even if it lasts forever!

    My Sailing Anarchy name is “On the Hard”

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