Sailing to Kaua’i with a Stranger

I was itching to sail away from Waikiki. So when all of the boat work was completed, I decided to sail over to Hanalei Bay in Kaua’i. Sailing between the Hawaiian islands can be hellacious. These islands are in the middle of the ocean and the water around them has that middle of nothing strength amplified by strong currents and turbulent winds that funnel fast between the headlands, saddles, and narrow gorges of the land. 

Everyone warned me that the sail to Kaua’i would be a breeze, and the return an unforgettable upwind sea-saw. “It will bend your mind,” they said. 

For me, sailing near land is way more frightening than crossing the Pacific. Near land there are; other boats, coral reefs, danger zones, submarine cables, buoys, kelp, currents, commercial fishing gear, explosives dumping areas, ship wrecks, and many other hazards to avoid. Near land, one has little time to sleep and one must always think. Near land, some say, more boats sink. 

As much as I like sailing alone, I didn’t want to go to Kaua’i on my own. 

I met another solo sailor named Sam. He crossed in June from Los Angeles to Hawaii on his 23 ft. boat, Sweedish Fish. My godfather, Jeff Fletcher, connected us. Turns out we were in the same marina, only five boats apart. 

Sam and I had the sea in common and our crossings and lessons were similar in many ways. We both left the mainland with no plan beyond, probably because we were not quite certain there would be a beyond to plan. That’s the reality of anything worth calling an adventure. 

Together we stared at human hair necklaces in a museum, hiked to a waterfall, climbed Koko Head, and pretended to be guests at a hotel swimming pool (room # 234). Still we were strangers.

When Sam asked if he could interview me for his YouTube channel, I suggested that the interview take place while sailing to Kaua’i. We made a plan to leave 3 days later. 

I checked the GRIBs and there was no wind in the channel, so I decided it would be best to head up the east side of O’ahu and get into the wind blowing out at sea.  

We left on a Saturday of the new moon. That morning we biked and skateboarded to the grocery store. Prepped the boat and left the dock around 11 am. As we exited the harbor surfers were shooting down waves off the port side of the boat and parasailors were flying in the air off of starboard.

When we first got underway, I had to face my jitters all over again. Twenty knots plus of wind, close-hauled, is not my friend. Even though Sam was there, “what if’s” ran rapidly around my head. What if we sink? What if we hit a reef? What if we hit a whale? What if we hit another boat? What if the engine breaks again? What if a hole in the sea opens up and eats me? My body became a drum. Bam-bam. Bam-bam. Bam-bam. 

I couldn’t think clearly? I couldn’t be present. I was on the verge of panic!

In my fluster, I set up Ruby (the self-steering windvane) wrong and my head was so clogged it took me far too long to resolve. Irrational thoughts can so easily fog a mind with clutter that steals its clarity. 

You are what you think. What you think is what you are. What you think, you are. I think, I think, I think, I am not on a boat. I think, I am riding a winged horse through a cosmic sea on the celestial sphere. I pass by an octopus smoking diamonds on Neptune, then I swallow the light of the stars. 

While I was battling myself inside, Sam was fighting against his seasickness. There we were, in love with this thing that can make one of us puke and the other scream. 

It took us six hours, heading upwind, to get to the other side of the island. There was a fresh breeze, small swell, and white caps.

Was it a mistake to sail to the east side of O’ahu? Had it added hours onto the trip? I don’t know, but I would rather sail than motor any day and drifting in dead air is such a drag. So what if it created a little extra distance between us and Kaua’i? 

Once on the eastern side of the island I was able to crack off the wind and we reached the rest of the way there. The boat moved good and the wind stayed strong. 

Sam and I were a good team onboard. He was so seasick that I did most of the cooking and sail changes. There were reefs put in and shook out and put back in. The staysail went up then came down then went back up. Together we jibed when needed. At one point I noticed a line had gotten loose and was moving freely across the deck and around the mast. It was my topping lift, which Sam was able to corral and secure back into place.

I discovered that an interesting thing can happen when I’m not sailing alone. The other person can question my choice of sails or tactics and I can begin to doubt myself. It is as if I never knew my boat at all. As if they are the expert and I their apprentice. As if they are right and I wrong. I kept having to remind myself that Juniper and I were one at sea, that I knew every inch of her, and could ride her in the waves blind if I had to.

This self-doubt is nothing new to me. I have always struggled with insecurity and lacked self-confidence. I have always found it hard to be me, to fit in, to fly free. When I am alone at sea, I don’t feel this way. When I am in a foreign country, I don’t feel this way. When I am with a close friend, I don’t feel this way. But, I can’t reduce my life to those scenarios. I thought somehow crossing the Pacific would help me overcome these unfavorable traits, but while sailing with Sam, I realized they were still there slouching in the pit of my being.

The full moon rose that night dressed in orange silk. I danced beneath moon shadows and the canopy of the Milky Way, while Sam slept.

We reached the northern coast of Kaua’i around moon rise the following evening. We were six miles from shore and the smell of earth was blowing off the island. It smelled like a forrest inside the boat and reminded me of digging for worms as a child. 

I think the scent was so strong because Kaua’i is pure country. It’s got more dirt than asphalt, more trees than people, more soul than you can shake a stick at. Some people say that island is too country for them to remain content, but I love country. Give me a city and I’ll rip it apart until I find a patch of earth not manicured by man. 

The wind shifted north, south, east, and west as we sailed parallel to the land. We ended up close-hauled on our final approach to Hanalei. The wind was light, the water smooth, and the energy was high. 

…… To Be Continued …..

5 Replies to “Sailing to Kaua’i with a Stranger”

  1. I hear and know your feelings are felt by many. Most do not test their limits but human you are and will always be. Lots of amazing adventures ahead for you.

    1. @annabaileycrlson, thank you so much for reading and relating your feelings. Means the world to me! <3 XO

  2. I stumbled upon Sam’s video and found your blog. I am not a sailor of the sea, but an explorer of land. All human’s have those traits you decribe whether one admits it or not. Safe travels on this rock we call Earth. May the Universe be with you as you learn and discover.

  3. great blogs and videos stumbled across your links while watching sam’s utube posts. Have sailed as ballast crew on various lake superior trips and am always impressed at good sailors which you are! Have fun on your journeys!
    Chukku Anderholm

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