I had been warned, but nothing could have truly prepared me for the sail from Kaua’i back to O’ahu

The day after the forest, Sam and I snorkeled, climbed palm trees that grew sideways, and watched an endangered monk seal beach itself.

Have you ever seen a wrasse? That species of fish is hard to miss, with their brightly colored bodies that look as if they have been collaged together by someone on acid. You see one and immediately think of lava lamps, black light posters, smoke rising up out of a bong, and long-haired women dancing. Their colors and patterns often make no sense. I have seen ones with pink stripes on their heads, blue and fuchsia polka dots on their bodies, and bright yellow tails. If you ever see a fish that looks like a bunch of different fish that have been glued together, sure as shooting, it’s a wrasse.

The monk seal was super cool. He shimmied further up the beach with each wave that hit the shore. I couldn’t tell which mask his face wore; was it boredom, or exhaustion, or total disregard? Land and people seemingly meant nothing to him. His Hawaiian name is “`Ilio-holo-i-ka-uaua” which means “dog that runs in rough water.”

The following day I discovered just how rough that water was.

We set sail around 11 am. It took twenty minutes to crank the anchor up. Our arms alternated moving forwards and backwards and forwards and backwards and forwards and backwards. Thats the beauty of not having an electric windless, you gotta work hard to get that sucker up.

As soon as the anchor was hanging loose, I steered us out of the bay. We waved goodbye to the green frontier and greeted the wet kiss of the blue.

Red-footed boobies flew around us for hours. Above, below, behind, to the left, to the right. There were more than we could count. Sam and I both had boobies land on our boats during our crossings. My best bird friend, Pluto, was a booby. I would like to think that Pluto and Sam’s bird friend were flying above us then. 

The return started out with amusement; we had a bowline tying contest with our eyes closed, and made music with my spare hoses. A few hours into the sail, Sam heard the phantom voices of Juniper. He was hearing things, not even I heard! He yelped, “What was that, who said that?” I smiled and said, “Don’t worry about that, Juniper is just haunted.”

It wasn’t long before the reality of the upwind trek set in and all our laughter fell away.

The wind was blowing strong from the exact direction that we needed to go, there were currents pushing us backwards, and Juniper’s rail was flooded by the sea. Each tack provided little progress. It was as if we were sailing in quicksand.

We were salmon swimming upstream, we were birds with broken wings, we were sailors smoking a pipe dream…. it was maddening. 

It took us 20 hours just to go 10 nautical miles. A starfish would have moved faster! That kind of sailing can wear anybody down. Put two people, who don’t really know each other, together in a space that neither can escape, and a situation like that can hit even harder. 

I wonder if anybody can ever really know another. I am still trying to get to know myself. I wander around perpetually startled by secrets sides of me as they fling themselves into the light of day. What cage of my body had I kept them in? Which of my twisted thoughts had fed them? Is that really me? Who am I really? Who is anybody really?

Sam and I were both used to sailing alone and had developed our own philosophies towards sailing. Under those circumstances, these differences were challenging. We laid around the prison of the boat, barely speaking.

Except for exchanges such as this- “Olivia, it looks like we are on a beam reach, we need to point Juniper higher into the wind, or we won’t make any progress.” Sam said. All of Juniper’s electronic instruments were off and he was referencing the Windex at the top of the mast, which points to the direction of the wind.

As soon as he said it, my insecurities started to rage inside. My ego was alive and thriving and stabbing me with negativity. It kept telling me that I was a terrible sailor and that I knew absolutely nothing. I was embarrassed. Did I even know what I was doing out at sea? Were Juniper and I no longer one!

I turned on all of the instruments, and stuttered as I said, “No look, we are between 50 and 60 degrees off the wind. That’s a close reach, not a beam. I can point her higher, but I am pretty sure that we will loose half our speed.” Sam just stared at me, so I followed with, “Either the windex is wrong, or all three of these other instruments are wrong.”

I could feel Sam’s annoyance with me. His need to get off the boat and be somewhere far away.

Sometimes I can feel what other people are feeling. Their feelings creep inside my body and make me want to shed my skin like a snake, again and again and again, until I can feel absolutely nothing. It is a blessing and a curse, and it is always overwhelming.

Someone walks into a room with a headache and I catch it. Someone has a stomachache, all of a sudden I am hunched over in pain. I walk into a space where people are high, and instantly I am the highest kite in the room. The other day, I was helping a woman who was choking. I got within five feet of her, then I started choking and gagging until I threw up. The worst is when I catch someones sadness. Once I was home alone and my ex walked into the room having just returned from a trip. I was so delighted for his return, but as soon as he walked in I was overcome with grief and became hysterical with tears. “Are you sad,” I asked him? “Yea, I have been really depressed lately,” He replied.

So yea, I cry a lot. Sometimes I cry my own tears, sometimes my eyes cry the tears of others. That day on the water, teardrops fell from my eyes, from Sam’s eyes, and from the sea’s eyes.

Teardrops because something we have always dreamt becomes real, because of the kindness of strangers, because we have to let go of someone that sang straight into my heart, because we are inside the wilderness of waves, because we haven’t truly slept in days, because we saw the sunset, because we saw a shooting star, because tomorrow is now yesterday, because the salt falling from our eyes is like the rain before the rainbow…because… because…because.

Anyway, on the next tack I didn’t fall off the wind as hard and I trimmed the sails in real tight. My traveler was squeezed in on the high side, the sheets were taught, and the outhaul was snug. I was testing my theory on loss of speed to shut my brain and ego up. It tuns out, the higher that we pointed, the slower we went. “Ok, I see what you mean, I think it is better to fall off a little and sail faster,” Sam said.

That first night, off the coat of Kaua’i, was the color of charcoal. The moon and the stars were covered in clouds and I could hardly see my hands in front of me. My navigation lights shorted out too and the smell of charred cables floated through the air. We were forced to sail under anchor light only. It was darker than dark. Each tack we did was all based on what we could feel. 

I’m not surprised about the lights with all the water we were taking over the bow. Juniper was heeled over like she was ready to tip. Water was rushing down the decks; my v-berth was soaked, the prisms were leaking, and the interior cabin floor was flooding uncontrollably on port tacks- seawater was running out from beneath the cabin stairs and turning the starboard-side floorboards into a river.  I used every towel and rag I had to combat it.

There must be a crack in my hull that is below the waterline when I am heeled over. I initially noticed the cabin floor leak on my final approach to Hawaii from San Diego. At the time I thought, “Is Juniper sinking?” Then I thought, “Hell, it doesn’t matter, I am almost to Oahu.” The leak has grown and now most certainly matters.

On a boat like mine, a persons weight has less of an effect on the balance, but keeping weight on the opposite side of the sails was important to me. Especially with all the water that was seeping in. And when it comes to Juniper, I can be just a tad bit controlling….just tad.

So anyway, I was adamant that we sleep and sit on the high side under these conditions. This really agitated Sam. He prefers the comfort of the low side, which is understandable, especially after he was thrown face down to the floor while sleeping on the settee. I still need to make lee clothes…oops! 

The next afternoon we finally made it around to the eastern side of Kaua’i and we were still only speaking when necessary, so it seemed. Long and liquid silences stringing us along.

Sam had a flight to Tokyo the following day, and we realized that we wouldn’t make it back in time. He wanted me to drop him off at a harbor on the southeastern side of Kaua’i. Nawiliwili is the harbors’ name. I like to say that name.

I wondered if Sam was really worried about catching that flight or if he just wanted off my boat so bad that he elevated its’ importance.

Heck, I could have crossed the Kaua’i channel alone, but I didn’t want to, nor did I want the journey to end on a note so quiet and sour. I said, “Pretty please don’t let me cross this channel on my own.” And he eventually agreed to push the flight back a day.

Then we spoke about the not speaking. Communication can cure anything. It can cure it enough to make a small boat feel much larger and little progress upwind feel much further. 

We made it to the thick of the Kaua’i channel and the wind and the current shifted in our favor, steadily curving us towards our destination. It was like the flow between us as humans, had created a shift in all the water that surrounded us.

The second night, the navigation lights still didn’t work and the boat was still dripping wet. We took turns waking up every hour to check on the world. Two solo sailors no longer desire the need for keeping a proper watch. If we both wanted sleep, we both slept and alarms were set. That’s how we had done it on our own, that’s how we did it then.

That night, when I opened my eyes, I saw a cyclops shoot blue arrows at my ancestors, I saw a metallic tree grow fruits made of diamonds, I saw a siren making out with a unicornfish, and I saw a plane parading around as a boat.

At the last hour before sunrise, I saw a massive ship coming straight towards us. It was the size of an apartment building and covered only in red lights.

I screamed, “Sam we gotta tack, there is a strange looking boat directly in front of us!”

Sam came out, looked at it and said, “Olivia that’s a windmill on shore.” 

“Who did I call to for guidance when you weren’t here?” I asked Sam. 

Honestly, when I am sailing alone, I pray and use my pendulum for guidance. My pendulum is made of amethyst and hangs from a golden chain. I would ask the pendulum, “Should I jibe?” And if it started swinging (yes) I would jibe. After I lost the use of my alternator, each night I would ask the pendulum if I needed to turn on the running lights or if the anchor light was enough. Each night it said anchor light, but then one night, when I was still five days from shore, it said running lights. I asked the question over again. “Are you sure pendulum? I am almost out of battery!” The pendulum started swinging to assure me that it was sure, so I ran those running lights. I woke up that night to see a ship passing me to starboard. 

Mock at my methods all you want, but that night proved to me just how right my pendulum’s advice was. Without my running lights on, that ship never would have seen me. 

Anywho, I believe in magic and God and aliens and I sure do love a good crystal, but enough of that hocus-pocus. Sam and I arrived back to Waikiki after 40 some odd hours. My refrigerator broke again as soon as we hit the dock and I discovered that most of my clothes had become petri-dishes for mold. 

Sam flew out the next day for his job in Japan. Before he left, we agreed that sailing and adventuring on shore together was more fun that doing it on our own. It’s a different kind of experience that doesn’t have the same rewards of sailing solo, but has its own. 

I have been feeling blue since we arrived back. I always feel this way when parts of Juniper are broken. When she leaks, I leak. But show me a boat that doesn’t leak, and I’ll show you a liar. 


*Sam and I documented our sail. Check out this Youtube video he made.

*A newspaper article about my crossing came out yesterday. You can read it here.

*I made a Wilderness of Waves instagram that you might enjoy.

* If you like these tales from the sea and are not already receiving them directly to your inbox, just go to, scroll to the bottom of any page, enter your email address, and click the “sail along” button beneath it. Then go to your email and click on the confirmation email that WordPress sends to you. Voila, now each post will sail straight to your inbox. Subscribing helps me continue this journey.


  1. You should sail Annapolis to Bermuda race June 5th 2020.

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  2. Any update on when Sam Holmes is going to post the video on his youtube channel? He should show the highlights of the trip on his channel and then link the entire video on your youtube channel?

    1. Hi Dan! I hear has been working on it, hopefully he posts it soon! I am going to make my own edit from the footage. At the moment I am making a music video of my sailing footage for a new track by Will Oldham that will come out in the next few months!

    1. Hi Dan! the video is now posted on Sam’s page (see above for link). I just finished a music that features me sailing and will be posted in December. Will send you that link as soon as I have it 🙂

  3. I too engage the assistance of an amethyst pendulum and it has never been wrong in regards to my boat. Great blog. I found it from Sam’s video.

    1. Haha Roberto if it is true, you know the pendulum doesn’t lie. Thanks for sailing along with me!

  4. The hardest part is finding the dead flat water required to obtain the information. Great blog , unique style, thanks for sharing.

    1. Actually the pendulum did, sadly, get it wrong regarding the results of last year’s Australian election. I only ask about myself and my girl ‘Peggy Sue’ now. I leave the big issues to those with mortgages and television sets.

  5. that is really cool that you a sam met and then sailed together. Such a cool experience watching and reading the two of you connect. You guys both share a passion for sailing. I find that really rare and beautiful. I wish you guys the best. Be safe.

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