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I Sailed Around The Country For 2 Years With My Best Friend (And A Dog): Here’s What We Learned


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Have you ever been asked to describe yourself in a single word?

I have a feeling most of us have awkwardly sat in an interview humming “um…” for far too long after being asked this question.  I recently received a message from a high school friend whom I hadn’t heard from in a long time.

She wrote, “I saw this word today and thought of you.”

The word was Quaintrelle. After reading the definition over and over again; I allowed it to soak in as a memorable and important compliment, unsure if this word actually described me, or if I just wanted it to.

It felt like even the people who didn’t know me very well had recognized what my purpose in life was before I had– down to being able to define me in a single word.

Quaintrelle – A woman who emphasizes a life of passion expressed through personal styleleisurely pastimescharm, and cultivation of life’s pleasures.

Now, if you could combine that definition with that of an untraditional, adventure junkie who can’t sit still then I would really have my “word” pegged. However, there is a difference between figuring out your word, and figuring out your purpose–which I am, of course, still working on. But spending the last 2 years on a 27 foot sailboat with my best friend and a dog helped me narrow down the “purpose” factor.

Three years ago, my best friend Katie Smith and I had this wild idea thrown into our lap by my father to buy a boat and sail to the Bahamas.

Yes, that’s right, my own father suggested that “his little girl” and her best friend hop on a sailboat and head for the ocean. With minimal sailing experience, and no ocean cruising knowledge, this idea seemed nearly impossible, yet we became addicted to it’s possibility.

Katie and I have been best friends since we were little girls. Equally as independent and free as we were responsible and focused, we both knew no one else in our lives besides her or I would dare to sail into the unknown leaving everything comforting and familiar behind.

The idea brewed, and brewed and kept brewing until it was so thick that if we hadn’t taken a taste right then, we would have missed our chance. After spending years being nomads wandering the state of California, in and out of school, jobs, and relationships, we decided it was time to take that chance.

We were buying a boat, moving home to Michigan, and leaving Fall of 2012 to sail from the Great Lakes to the Bahamas. Slowly this idea became a reality as we worked in restaurants to fund the trip at the same time we were gutting and renovating an old sailboat that needed more TLC than an abandoned crystal meth lab RV. 

Just because this idea was handed to us, doesn’t mean anything else was. The process of buying and fixing up this boat constantly distracted us from the whole reason we took on the project in the first place. We poured our time, money, and hearts into making this boat a functioning home. Over that summer we learned about mechanics, plumbing, electricity, dedication, and how having dirty fingernails could be sexy.

It was the most frustrating project we had ever gotten ourselves into. Pretty sure I was ready to strangle my dad when he had me sanding bottom paint and eating fiberglass. We were also ready to throw in the towel when a plumbing project turned pretty shitty–if you know what I mean. 

Weeks before departure Katie’s Uncle sat us down and recommended that we should wait till the following year, to give us more time to prepare. This wasn’t just a day sail. It was nearly 3000 miles of “we haven’t the slightest clue of what is going to happen next” sail. Katie and I didn’t really talk for a few days. We both thought maybe Uncle Tari was right. We weren’t ready. We had only sailed the boat three times. After being discouraged and thinking about everything we had already done to get to where we were, made us realize that there was NO WAY we would wait for the following year. There was just no way. We were going. 

So we did.

On September 4th 2012, Katie, her dog, Reggie, and myself took off into Lake Michigan aboard our sailboat and new home “Louise”.  We motored down a series of rivers consisting of the Illinois, Mississippi, Tennessee, and Tombigbee waterways leading us towards the Gulf of Mexico. Right about the same time it took to adjust to our new simple way of living/camping, we were out of money. It took us three months to get to Florida, where we spent a season waitressing– again. After slinging never-ending food and drink we eventually saved enough to head towards our real destination. By that time we hated living at the dock and were hungry for the ocean. Carefree and fearless (not true– we were both terrified) we headed for the Bahamas. 

Arriving at these islands was far more magical after a year of preparation and anticipation. Like anyone, we could have hopped on a plane to be there in a day, but instead we traveled 25 miles a day at 5 miles an hour. I could have jogged faster. The day we crossed the Gulf Stream to the Bahamas, we were nervous. I remember being sick to my stomach, my mind filled with everything that could go wrong. That afternoon, Katie caught a big ole tuna, our first catch. I wasn’t nervous anymore, but overly excited. I cried when my eyes caught first sight of the Bohemian land we had worked so hard to get to. 

There we were surrounded by an indescribable landscape, at the mercy of Mother Nature who quite frankly; didn’t give a damn we were there. When the engine broke down – there was no wind. When we needed help – there was no cell phone. When we were certain massive waves would sink us– we kept going. When we sweat ourselves to sleep – there was no air conditioning. When we could see our breath in the morning– there was no heat. When it rained – we got wet. When it stormed – we got scared. When we were hungry – we opened a can. When we were dirty – we jumped in the ocean. Three months of island hopping, storm dodging, and problem solving became the stories we will be telling for the rest of our lives. You get the point. The point is, we learned what we were capable of. 

When I was a teenager, Katie nicknamed me “Brave”.  Which in return made me believe that maybe I was.

From ages 18-22 I sort of thought I was invincible. Now at 25, I’ve learned that being brave doesn’t mean being tough, or invincible. Being brave can be as simple as allowing yourself to cry, finding a way out of an uncomfortable situation, having a hard conversation, or just accepting yourself. On this journey I was humbled. I learned to slow down. I learned to know myself before anything or anyone. I learned the importance of friendship, and the importance of communication. I learned that it’s okay to ask for help, and that it is okay to mess up. I learned that I am composed of emotions, self-awareness, situational awareness, and now experiences that have done nothing but enable me. Oh, and I supposed I learned a thing or two about boating.  

Having a purpose is an ambition that some people go through life not paying any mind, while others spend years stressing over what exactly it is and how the hell they are going to find it. I fall under the latter category. I have allowed it to eat away at me to the point where I’ve lost all confidence and am ready to jump ship. Literally. But by having this ambition and going on this adventure, I’ve learned something very important; what I am capable of. And discovering what you are capable of raises your bar higher than you ever thought you could reach. Be untraditional. Be brave. Be passionate. But do so in your own way, and on your own time. Be a quaintrelle.

I have documented Katie and my journey here KATIEANDJESSIEONABOAT.COM.

Through photography and writing my effort is to share with you the best and worst of times, in hopes to get other women to think beyond what they believe they are confined to. You can check out more images of our journey below. 


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