Once upon a time, my best friend asked me if I wanted to buy a cheap ticket to the warm, lavish waters of the Caribbean. Whether it was the cool fall breeze on my skin or my inability to turn down a new place, I, of course, said yes. 

We wouldn’t know until we were on our way to the airport that our new home would be 36 feet long and 10 feet wide. It’d be floating, rusty, rustic and answer to the name Southern Breeze. In between the swimming, snorkeling, reading, star gazing, cloud watching and napping, we learned a lot about ourselves, about the world. But most importantly, about how the world works — and how it doesn’t.

Living aboard a boat that’s only good for floating provided us with a wealth of life lessons, including but not limited to:

You will fail.Caribe 063

My god, you will fail. I have never lived such a period filled with high highs and low lows. And not only will you fail, your boat, or its engine or radio or a largely significant part will. You’ll be so ecstatic at your life, at the scenery, at the smiling faces surrounding you. But you will also be frustrated to the ends of the earth with island time, lack of convenience, an endless list of broken things to replace and fix and your lack of funds (I recognize the sailors dawning 51-foot yachts with bathtubs don’t relate to this). But you will learn how to fix/ignore the problem, and move on with the day. You will learn what is important to focus on (the turtles, not your lack of job prospects) and what can be dealt with at a later date.

Things will go overboard (i.e., wrong).

Remember the first day you lived on a boat? All your eyes saw was a sailboat on turquoise waters surrounded by turtles and sunshine, all you felt was the subtle breeze on your skin, all you tasted was the salt on your lips and freedom a floating home would allow. By the second week, you could look past the mussels covering the hull, find the humor in your lack of working radio, sails, dinghy and the water dripping onto you from the leaking ceiling above you each night. You could brush off the likelihood of the mooring line last being checked before you were born. But after a month or so, you’ll start to get concerned when gale force winds move in and you don’t have a way to charge your dead phone, enough food on board to last more than three days at sea or lifejackets to wear in your sinking, borrowed rowboat. The key is to work with what you have, not what you don’t have.

Know what you’re saying yes to. Caribe 086

“Our neighbor is moving on shore and is willing to rent you his sailboat for $100 a month if you girls are interested,” Tonga’s aunt Becky told us as we drove to the airport. We were planning (really, the only thing we had planned) on staying in a hostel until we figured out a more affordable winter home. What’s more affordable-and more fun- than a boat? And who says no to a boat? That was about the extent of our thought process when we said, “we’ll take it,” with no hesitation whatsoever. What we didn’t think about was how we’d get to and from the moored vessel, how we’d fill our water tanks, store any food, charge our phones and pay for broken parts, a dinghy or gas. We certainly overlooked the “project boat” aspect when we first set eyes on Southern Breeze. It was more about the fact that it floated, was well within our budget and that it seemed like a neat thing to do. To say we were impractical about our decision and overlooked a few things would be quite the understatement. We should have asked our sealord ahead of time who would pay for a ladder or the bilge pump when it breaks before those issues came up.

Safety is key.

When we first moved on board, we had no ladder. If we jumped or fell into the water, there was no way of getting back up. Before this was resolved, we would jump in and swim to a neighbor’s boat, bribing them to dinghy us back to our boat so we had a way to get back on. This somehow always happened around dinner time, and we were handed plenty of meals in the process (whether it was because we just swam across the bay, we appeared poor due to our lack of dinghy or because the cruising community looks out for one another, we’ll never know for sure).

Mentors are invaluable. image (1)

One night, after camping in a leaking tent during a torrential downpour, set up over hard roots of Bay Rum trees, we stumbled into a surf shack. The owner, a weathered surfer with wild curls and an infectious zest for life, was staying late that night and poured his wisdom and life advice into us until the wee hours of the morning. His name was Kendall and gave us a huge list of places to apply to and people to talk to about jobs. He also gave us plush mattress pads, apples and motivation to go out into the world and kick some ass. Since then, we refer to the question that guided us during our time in the Caribbean whenever making life decisions: “What would Kendall do?”

Have vision.

When you buy a one-way ticket to a place you’ve never been to before for kicks with a plan of “getting there and seeing how things evolve,” you must pack your patience. You can’t expect everything to fall into your lap, and you certainly can’t get frustrated when things don’t play out as flawlessly as they did in your daydreams. It is important to have some sort of idea of how you want your days to look, lest you want your life to be filled with random tacs and turns, complete with a Kon Tiki drum soundtrack, drifting away with the tropical beaches in the land of manana. I suppose that might sound nice to somebody. But for me, it was pure purgatory to not fill my days with purpose.

Be resourceful. image (8)

Don’t have money for a dinghy? Perhaps a borrowed, battered rowboat the size of your average coffee table will do. Who cares if you have to spend 15 minutes bailing out the water every morning and the oars are two different sizes? Whatever allows you to get back on the boat and get to and from shore without having to rely on your best friend’s cousins to paddleboard you each time you forget your shoes on shore. Plus, there’s an extra element to your fitness motivation when you face oncoming cruise ships crossing the main channel.

Stay positive. sb2

Things can change drastically day by day. Jobs may seem in your favor one day and you may be shit out of luck the next. The next, your wallet may be too small for your $50s and your diamond shoes may be too tight, but then you might wake up to a sinking rowboat and no water the next. Despite the lack of change in the weather, life still wavers. To stay positive while facing so many unknowns, like the elements or open water or a lack of job prospects, it’s so important to focus on the good, to keep negativity out of your thoughts. It’s not like we actually ever were on a sinking ship. We always had the option of swimming away to safe ground if it was really necessary, which eventually, it was. To find and appreciate the humor in your po-dunk, uncommon life will make it so much more fun to live. We liked to say, “We’re short on funds but not on fun!”

Don’t consult a Magic 8 Ball for your life’s problems. 

Perhaps you don’t actually need to go live on a project boat to figure this one out. What I mean is don’t let something or someone decide your life for you. Don’t be passive about it. Make a decision to do something and stick with it until it doesn’t work for you, and then choose something else. But do choose and keep choosing. Otherwise, you’ll find yourself with no job and no money, sitting on a rusty boat, asking a black ball, “Should I stay or should I go?” Only to be faced with the hopeless response of “Ask again later.”And then you’ll wait a while longer to not make a choice and not do anything, ever.

Spend as little time indoors as possible.  Caribe 127

Boat life is bliss. I remember one night, after we had been camping for about a week on St. John, I slept on the couch in my coworker’s living room completely surrounded by walls of windows and two sliding doors. When I stepped outside in the morning, I felt like I had been deprived of nature the past 10 hours. At the time, I did not ever want to sleep inside again. All that fresh air, vitamin D, time in the water, waking with the sun and reading by the light of the moon was so natural. I didn’t care that my meals consisted of the choice of black or pinto beans, I cared that I was living in tune with the environment around me.

Don’t rely on Kmart’s outdoor equipment. 

When Kmart is your only option for shopping and you don’t know anyone who owns a tent because they all live on a boat, and you know it rains every night so you need some sort of cover, you take your chances. If you’re a loyal REI member and devout backpacker, buying a tent at Kmart steals a bit of your soul. Our options were either a 10 person tent, a 12 person, or 4 person. We took the last remaining 4 and shelled out $80. It comes to no surprise that the tent will let you down entirely. It will leak. Roots will crawl through the seams and leave room for the bugs to infester your skin. You will be better off with a tarp.

Find a way to laugh at your situation.

In the end, we ended up facing 70-80 hour work weeks serving, making $2.83 an hour plus tips and sharing a studio apartment with a nit-picky girl. Living inside wasn’t very fun. Life on the island wasn’t our cup of tea, we started referring to it as a sunny place with shady people. A man ended up following Tonga back home one day and said enough to make her lock herself in the bathroom for safety and sleep with our sharpest kitchen knife the next four nights, anticipating his return. I think it’s important to note here that our door didn’t lock from the inside. Our sense of safety was totally shaken up, we had totally dead end jobs and had been defeated for weeks, saying things like “Oh no, you rolled your ankle, now we both have to go home.”

It’s okay to know defeat. It’s good, in fact. Caribe 079

You will be thankful for your safety, decent job, not being limited to an island, having some form of transportation-even if it’s your feet and you don’t have to swim to get to work-for your friends who want to do more with their life than drink sundowns until sun up when there’s a lush national park a mile from where you rest your head at night. You will be thankful for when you’re content being where you are, when you have a refrigerator or running water or more than a can of beans for dinner. But god damn, you will miss jumping into that water.

NEWS FLASH: Nobody cares about your life.

You think your life is hilarious and entertaining and all that is missing is a studio audience and $80,000-an-episode salary. But boat life will humble you. When you’re stranded, just wait and see who comes to your rescue. When you say you can’t find a job, count how many people feel any sympathy for you in “paradise.” It’s up to you to make your life happen.

Guest Contributor

Shelby Huff is a wildlife guide, editor and writer. She hails from the Pacific Northwest, ping-ponged her way across the better part of the Americas for a few years, living out of service, out of a backpack and sometimes out of her truck. She now calls Wyoming home. When she’s not on this wild goose chase of becoming a writer, she can be found compulsively researching van life and living off the grid, on a mountain, or on some sort of boat.