Sailing Solo in Search of an Endless Sunrise

At the beginning of August, I am sailing solo across the Pacific Ocean from San Diego to Hawaii. It is one of the longest ocean passages in the world, with nothing but a wilderness of waves between the land.

The Pacific was named by the Portuguese explorer Ferdinand Magellan and it means “peaceful,” which makes it sound like sailing on it is as easy as pie, but from what I know it’s a lot wilder than that.

It is open ocean tousled by the collision of high and low pressure systems that conjure typhoons, hurricanes, and cyclones into existence. It is 750-million-year-old water that rests above a tectonic plate in a perpetual state of subduction. It is a galaxy of deepwater trenches filled with glowing-eyeless-alien creatures. It is a valley of submarine volcanos. It is the great ocean of Kiwa. It is a Ring of Fire.

People think I am brave, but I never wanted to sail across it alone.

In fact, I am afraid to go alone. I am afraid of a lot of things. Like elevators, lightning, and the sound of my own voice. I am afraid of falling overboard. I am afraid of growing old. I am afraid of my own thoughts. I am afraid of the ghost of yesterday. I am afraid of sitting still for too long. I am afraid of dying alone. I am afraid to wake up one day just a dreamer with a dream that wilted beneath the firestorm of fear. A dreamer tethered to a cloud that dissipated into sinking air.

My dream of setting sail always dripped with the hot nectar of romance. It involved me and some handsome fella who could take care of all of the electrical and mechanical shit, while I made the sails dance in the wind. I have been so obsessed with this idea that seven years ago I broke up with a live-in lover because he had no interest in sailing. Since then, I have had a string of boyfriends who sail, from 3D gun-slinging Republicans, to pirates who stole my jewels, to gypsies who floated in a hazy shade of reality. For my love of sailing and the pursuit of a sailing companion, I was able to ignore the obvious signs of incompatibility and even willing to bend myself into impossible shapes to keep that toxic flame burning.

Still I held onto the dream.

I was supposed to sail to Hawaii this summer with my most recent Romeo—a gypsy in case you were wondering—but a few months ago our love affair exploded and I found myself about to turn 37, partnerless, and living on a boat still shackled to land. I realized that even though I had over 10 years of sailing experience and my 50 ton captain’s license, my romantic notions of sailing with a mate were built on the fact that I didn’t have the self-confidence nor self-trust to do the repairs that go along with sailing. I realized that in my quest to fill this sailing partner void I had sacrificed self-love. I realized that there was nothing getting in the way of my dream, but me, and I wasn’t going to let another year drag by in search of that perfect someone to sail off into the sunset with. So I decided to cross the Pacific alone.

In order to do so, I first had to identify the origins of my fears.

I had to find the heart of that coward that crept around inside of my head and try to shoot her dead. And I had to let go of all of my ponderings involving risk and probability if I was ever going to embrace the unknown.

I discovered that the more you know, the more you know there is to fear. For instance, as a kid I used to do triple flips off a high dive until I saw a boy bust his head open. The image of his blood filling the pool still stains that memory. I’ve never done a flip since.

When it comes to sailing, I’ve been dismasted off the coast of Bermuda. I’ve broached on the edge of a tropical storm. I’ve run aground by the Statue of Liberty and been stuck there for three high tides. I’ve been knocked down four times in a row with a mast horizontal to the water and a spinnaker dragging in the sea. I’ve been on boats where we had to MacGuyver voltage regulators with lightbulbs and I’ve had major engine failures uncomfortably close to shore.

None of these situations required screaming “Mayday” into a VHF radio and all of them added some sweet sugar to the adventure, but I wasn’t alone in resolving them. Could I handle situations like these on my own? That is what the coward inside my head wondered.

I have spent the past two months working 14 hours a day to make sure that I am prepared to handle any situation that the high sea throws at me. I have studied and repaired every nook and cranny of my boat under the expert guidance of a former America’s Cup boat builder. I have learned to use power tools that I never knew the names of. I have learned basic electrical rewiring along with a clearer understanding of my 12-volt system. I have crawled into tiny spaces to repair and study parts of my engine. I have learned how to deploy a life raft. I have learned how to cut down my rigging with a grinder. I have learned how to scale, gut, and fillet a fish. I have learned how to anchor on my own, to pick up a mooring ball on my own, to lift a spinnaker pole on my own, to reef the mainsail on my own. I have learned how to use a self-steering windvane and I have practiced plugging my thru-hulls with seawater spraying inside of my boat.

Am I ready for this? I don’t know, but I am brave enough now to try.

14 Replies to “Sailing Solo in Search of an Endless Sunrise”

  1. Wow and Wow and WOW! You are one unique woman going on a unique voyage, and I say “bon voyage.” May all your dreams about this adventure come true, and may the book it builds for you come sailing into the world.

  2. No doubts about the strength of your heart, body, mind from the moment I met you. Your sunsets await!

  3. You’ll be great. Self sufficiency is the ultimate high and no better theater to practice than blue water. Everything is infinite including your capacity to sort out the bumps as they come. Nice hustle Olivia, have fun 😉

  4. Your blog is very fascinating and interesting, did not know you have been coast to coast, great life’s experiences that you undoubtedly will use on your journey to Hawaii, you will have many thoughts and prayers going with you.
    We will look forward to tour blogs as you go, be safe??

  5. The mother in me wants you to wear a life jacket at all times, and a GPS necklace. I’ll be watching. I’m nervous for you. The best of luck!

  6. Olivia! You are always inspiring and truly amazing! I wish you the very best on your quest. You’re a formidable warrior and intrepid explorer! May Mother Ocean look over you and commune with you!

  7. Just a quick hello from the furthest point backward WP is allowing me to go. But the comments above lead me to believe there was earlier work. I shall have to look again tomorrow, or later today, depending where your sail is filling right now.

  8. Hi Rawgod, you found it! This is the beginning! I have been sailing for 10 years, but this is my first blog post and this is my first solo expedition 🙂 Enjoy the journey. x

    1. Ahoy, Olivia! I was trying to find your first blog post, too, and re-read your journey from CA to HI — glad I stumbled across this reply you sent to rawgod! Can’t wait for the Q&A coming up next week!

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