8 Reasons Why My Sailing Dream is Dead

By Mr Defy

I have never had a dream so completely shattered and destroyed as this sailing dream.  I have been day-dreaming about sailing since I was 17.  Reading books, watching movies, but never getting onto a boat while living in land-locked states.  I dreamed of slow travel and being able to experience getting to a place rather than waking up on a flight and you’re already there.  I dreamed of sustainable travel, independence within “international waters,” and working on new skills during long passages (like meditating or reading all those books still on the shelf).  I imagined going to far-flung locations only accessible to intrepid sea travelers and seeing natural beauty away from cruise ship routes.

And then I did it.  In fact, we both did.  We dove head-long all the way in- a 10 day to 2 week sailing adventure from Dili, Timor-Leste to Raja Ampat, Indonesia.  It checked all the boxes on what we wanted to try- remote snorkeling locations, islands only accessible by boat and a multi-day ocean crossing with night-watches.  If we were going to love it or hate it, this would give us plenty of information.

It started off strong with snorkeling along an unbelievable reef, swimming with glowing plankton and anchoring by a remote island village where all the residents came to look at the boat as the night’s main attraction.  But it was tough to tell if I liked it in those first days because of the boat and captain.  Miss Defy would ask me, “So what do you think?” I’d say it was like trying a new food at a restaurant and you think you enjoy it, but there’s a heavy metal, incoherent garage band shaking the dinner table with ear-crushing music.

For starters, the captain was just barely clinging on to his sailing lifestyle.  The first thing he said when we met was, “Thank God you’re here, I was running low on funds and wasn’t sure what I’d do without you.” Kind of an odd first impression, no?  Then we walk down to the shoreline- boats in the bay, dinghies on the beach.  My eyes glanced up and down wondering which dinghy we would be on.  I almost completely passed over the grey dilapidated one if not for his lack of funds statement still tumbling around in my head.  This dinghy was underinflated (it had a slow leak and needed to be constantly pumped up except he forgot the pump on the boat), barely had room for 3 people (let alone their gear) and was probably thrown out by another sailboat before our captain said, “Oh no, there’s still a lot of life left in that one.”  Literally every time the captain started the motor, he would tap it and say, “That’s a good one” in a superstitious, thank God it worked kind of way.

While trying to sit on the tiny boat so the small (and formerly innocuous) waves didn’t crash into the side and get your shorts wet, we looked ahead for the vessel of our upcoming adventures.  From the outside the boat seemed fine.  It was the inside that carried through the captain’s cheap, neglected style.  Dirty dishes in the sink, clutter just thrown about with a peculiar musty/old cigarettes smell lingering.  Not at the hoarder level, but the lived-in RV you visit and suggest hanging out together outside.  The pillows he gave us had blood stains on one and mold on another.  Our one sheet had armpit-like sweat stains from previous travelers.  “There are ants,” he warned.  “If you see any just squash them with your thumb so we don’t get more.”

Red flags, of course… but our enthusiasm prevailed.  The first night on the boat Miss Defy and I had a conversation about if we were actually going to stay and decided we could endure it.  We had spent so much time and money finding a boat and getting to Timor-Leste.

And then there was the captain.  There are officers who have inspiring leadership qualities with behaviors you want to emulate, and then there are people who buy a boat and now expect everyone to call them captain.  Ours was the latter.  A very short-fused, socially awkward individual who wouldn’t surprise anyone in saying he’s lived on a boat by himself for 25 years.  The type of guy who has his plan, will execute it how he wants and snaps at anyone involved.   

I found myself in so many odd human interactions.  At one point he called me over to talk about how he felt disrespected about the dishes.  It is Miss Defy and I’s habit to clean our dishes after we use them and if your roommate doesn’t clean their dish, that is their business.  The captain was that messy roommate.  He’d use a dish for breakfast, lunch and maybe a snack in between and everything would be thrown into the sink (at port, mind you, where there is no immediate need to get back up and check how the boat is sailing).  He said when he was sailing without company he would typically let the dishes stack up for 4 days before cleaning the massive pile (was that when he ran out of dishes or the smell became overwhelming?).  In the evening after our communal dinner I would begrudgingly wash all the dishes in the sink instead of trying to sift through which dishes were from dinner.

So the captain sits me down and says, “I feel disrespected about this dish situation.  You and Miss Defy use a plate and then immediately wash it, but you leave mine behind.  That seems intentionally disrespectful.  You already have a soapy sponge in hand, why not take care of all the dishes?”  Because we’re adults, captain, and we’re not here for 2 weeks to clean and take care of you.  If we were paid crew or here for free, maybe he would have a point, but Miss Defy and I were paying him $60 per day per person to “join-in.”  On one hand he’s the captain and we are the crew- we have to do what he says, but on the other hand we’re hiring him which changes the dynamic and raises our expectations.  Besides- if I do the dishes at night it seems like you’re already 3 days ahead of your normal timeline right?

There were a number of other interactions that still baffle me: like him insisting we go to 7 different grocery stores (with 13 trips because some stores he had to go to more than once) on foot in the equatorial humidity, him fuming about how we couldn’t follow simple instructions after he couldn’t find us at a coffee shop we said we’d wait at (he missed that there was an upstairs and still blamed us for incompetence), but this post is about a dream destroyed.

I tried to look past his oddities and the boat’s former meth lab vibe to see if I liked distance sailing.  I went from, “Okay, okay, maybe I like this.  Sea turtle, cool fish, wow glowing plankton.” to “nope, nope this is terrible, I have all the information I need, no need for an additional 2 days on board.” 

Here’s why I’ll never willingly go distance sailing again-

1. It’s slow– like mind-numbing interminably slow.  You can’t check the GPS for your progress after an hour because it looks like you haven’t moved.  You listen to a podcast for an hour, look at the waves and horizon for a bit, and make sure the sails are up appropriately.  If something breaks you get to change the routine.  You can read but you need to look up every 5 minutes to make sure the auto-pilot is still going the right way.
2. The auto-pilot can take care of it– there was a lot more managing the auto-pilot than sailing.  After setting the sails in the right direction, the majority of sailboats use auto-pilot so they don’t need to actively steer.  In other words, you’re sitting a lot. 
3. Lack of sleep–  Sleep is precious and in short supply when crossing an ocean (even a shorter 3 day one like ours).  The boat is rocking (and not peacefully as in a lullaby nor does it have any anticipatable rhythm), it’s humid and probably hot.  Add in our captain’s chain-smoking and the sound of the engine housed in the kitchen and you get the idea.  During crossings someone always has to be on watch so you break it into shifts- there goes half your sleep right there.
4. No exercise– Maybe you’ll go for a swim if you’re anchored in a cove and maybe you’ll strengthen your arms while pulling sails up or down (with pulleys and gears to help) but say goodbye to cardio workouts and lifting.  There just isn’t space for the extra equipment and it’s challenging to do while the boat is rocking back and forth.
5. The cruising community– Mascotted by our captain, we found the cruising community to be different than we anticipated.  We thought it would be a group of sustainability minded, adventure driven people.  Instead we found people heavily drinking, sitting around, and without much direction or plan. This was true of cruisers met during our time in Thailand, Indonesia and Timor-Leste.  I realize that not all boat-owners are the same, and there must be more like-minded sailors out there, but our foray was not inspiring.  When we arrived in Ambon our captain immediately started scouting for other cruising boats to go visit, and eventually found one he would meet at the bar later.
6. Seasickness– I wish I didn’t get it, but the seas got rough and I felt terrible.  I thought I was doing great, the first 2 ½ days I had no problems.  Then we did the nonstop sea-crossing with larger waves and no breaks in coves.  The following 2 days I was down for the count, not eating anything because I’d immediately lose it.  They say it gets better with time, that you’ll find your sea legs.  I’d say “But why? So you can check an autopilot every 5 minutes?”
7. No cooking– I was excited about having a kitchen again but during crossings you’re eating easy meals.  Cooking might be different on larger, fancier boats.
8. The entry/exit process– This was absolutely painful and something I was completely new to.  We were part of the process for 3 countries- Thailand, Timor-Leste and Indonesia and none of them had the same process.  You have to go to 4 organizations in different locations- harbor master, quarantine, customs and immigration.  Some steps need to happen before or after others.  Some want to see and step foot on the boat.  Sometimes they’re closed for lunch.  Sometimes the guy you need is in the neighboring city should be back soon.  All this in a foreign language.  Get ready for more waiting (but you’re probably prepared for the waiting after sitting on the boat for so long).

Miss Defy read this list and found yet more reasons to never go distance sailing again.  Here’s a bonus 3 from my wife:

1. No shade– I love the sun and the heat, but at some point you want some respite. On this boat, there was only one area of shade, and with 3 people, it was usually only the captain that lounged in that sliver of darkness. On the rare occasion when I was able to snag the shady spot, I was still graced with the sun reflecting off the water. I could always risk going into the cabin as we swayed back and forth, yet that would inevitably result in a ball of stomach acid (all that remained after days of not eating) launching out in less than 3 minutes. Therefore, I continued to stare at the horizon while applying massive amounts of sunscreen, and hoping I wasn’t burning to a crisp.
2. Stuff breaks– In the middle of nightwatch on day 2, Mr. Defy and I watched the half-inflated dinghy break off a pulley and begin dragging behind the boat. The waves were large, it was late, and this was the last thing we wanted to deal with. We were only 30 minutes from changing out shifts, bored from staring into the darkness, and this POS has the audacity to break off the back? Yep. And if I owned a boat things like this would break at the most inopportune moment over and over again? No thanks.
3. Weather– Bad weather is unavoidable. Why? Because mother nature doesn’t care if you are on a boat with a perfectly placed mast (aka lightning rod) begging her to go away. She just does what she wants. At one point, we had 3 thunderstorms on all sides of us, enough for the captain to put his laptop and tablet into the oven for “protection.” I saw dark, ominous clouds and watched as waves erratically came from all sides jostling the boat like a pinball. My only consolation was finally something in nature was reflecting my attitude toward the whole experience, but I decided being in the middle of the ocean is the last place I want to be in a storm.    

So, I am out.  What was supposed to be a 2 week trip lasted 5 days.  My romanticized (but never experienced) dream of sailing around the world is ripped to pieces like how I would have liked to do with those moldy, blood-stained pillows.  One on hand I’m sad that the dream is gone, and I wasted so much time thinking and imagining about it.  On the other hand, I’m glad it’s over, glad I won’t be spending the next 15 years thinking how great distance-sailing would be only to find out then.  I’ve learned I need to get out and get a taste of the dream sooner instead of keeping it pretty and polished in my head.

I’m also incredibly grateful for this year off.  The flexible schedule was crucial in finding a boat.  What a disaster this would have been if we bought a $50-$100k boat only to find we dislike it. 

And finally, I’m grateful for my wife who agreed to this hare-brained adventure.  I can’t believe I dragged her along on this pursuit and I owe her a lot.  Her patience, ability to stay composed while uncomfortable/grossed out, and her resiliency following difficult situations made this challenging experience so much better.

If anyone is looking for me, I’ll be in the mountains, far from any shorelines.