“If it terrifies you so much, why do you do it?” my mother asked.

I was about to leave for Port-au-Prince to sail on a relief yacht through Haiti, Jamaica, Cuba, and the Cayman Islands. I was popping anti-anxiety meds, losing sleep, my fingers itching to call it all off. To retreat into safety.

I had never seen the boat before. I had never met the crew, and they had never met me. When it came to sailing, I was still a beginner, at best. I knew virtually nothing about them–except that I wanted to share their journey. So why?


Growing up, I was the girl who should have been voted “least likely to get on a boat full of strangers and sail across the world.” I got straight A’s, but didn’t dance, drive, play sports or even order in restaurants for 10 years for fear of getting something “wrong.” To be un-right, un-perfect, was literally the most terrifying thing I could possibly imagine. The only solution was to never do wrong things, to never do imperfect things, and to never put myself in situations where I might have to.

Eventually, I was diagnosed with depression and anxiety. I still take medication, and have been in and out of therapy. I thought it would be my life, until at eighteen, I read The True Confessions of Charlotte Doyle by Avi, a tale of a spoiled 18th-century girl who’s forced to put on pirate clothes and climb the rigging when she’s caught in the middle of a mutiny.

Charlotte was forced to become a sailor; I chose it for myself. When I went to sea for the first time, boarding a schooner off the coast of Vancouver Island, Canada, I chose to be uncomfortable, to be scared, to be tossed like a sack of potatoes into situations I didn’t know how to handle. The first time I had to help raise the main halyard atop the cold water of the Georgia Strait, I wanted to dissolve into ooze when someone laughed at me for not dropping the rope soon enough. Still, every time I get on a boat, I have to remember to walk on the high side, to tie a bowline, or to duck when the boom comes through on a tack. I know oodles more than I did, but as even a captain can tell you, the learning never ends–and neither does the screwing-up. But the good sailor has the ability to look into the imperfect; the unknown, and smile.

Moreover, sailing is like no other form of travel in that it forces my human interaction. At sea, there is virtually no escape from my fellow crew other than throwing myself overboard. Every time I board a new boat, there’s that moment where I will meet the small group of people who will share this cramped, musty little microcosm, and who will not only become my friends (or enemies, or lovers–yes, it’s happened)–essentially, my family, for the next two weeks, two months, or two years.

Something about the impermanence of the sea–the ever-changing wind, the currents and tides–forces me to embrace imperfection. And now as I prepared to leave for Haiti, I asked myself again, why?IMG_20160327_111347930_HDR

It was guaranteed that I will get saltwater choking my nostrils and bruises all over my body, and the seasickness will make me wish for the sweet release of death. I will sleep in damp clothing, I will smell like mildew, and I will be forced to take cold showers in spider-infested Cuban marinas. I could have hopped on a plane and been to Grand Cayman in three hours. But I chose this.

It’s no secret that few women choose this mode of travel. The ones who do go a little further, push a little deeper, live lives a little braver. Like me, like all of us, they’re afraid of what could happen; of being laughed at, of being scared, of being alone, of being hurt. But they do it. And in doing it, they remind me that this choice I’ve made can’t be as wrong as I sometimes think it must be.

It’s hard to keep dwelling on myself when I learned that the Dutch girl on the Haitian boat took a year off from medical school to hop yachts and backpack through Cuba solo. The 40-year-old Canadian who divorced her husband and left her corporate job in Toronto, only to reinvent herself as a kiteboarder and sailor on the reefs of Belize. And the apple-cheeked girl I met the on the Dutch schooner Oosterschelde, who took a gap year off before university to sail 9,000 miles over the equator to become a “shellback.” Like me, all of them were outnumbered by men; all of them were consumed by doubt and loneliness; at various times, I saw all of them cry.

And all of them are still sailing. We never ask each other why.

Sailing has given me the privilege of shutting off Facebook and Instagram and CBS and CNN. To cross foreign borders as if they didn’t exist; to dance the salsa in Cuba as if I weren’t an American but a citizen of the world. To hitch a free ride on a Jamaican police boat when I came in too late from a dancehall, then learn to surf in Port Antonio, seeing stars on jerk chicken. To launch from Ushuaia at the end of the world, then fly with hourglass dolphins through a pink sunset off the coast of the Falkland Islands.IMG_20160302_092659022_HDR

Or to port-hop, dropping off saxophones to marching bands of street children in Ka Kok, Haiti; to creep onto the beach at Ascension Island at midnight to watch sea turtles lay their eggs under the full moon. To drink pints in Horta, Azores, at the most famous sailors’ pub in the world under the flags of ships of a hundred nations. To blearily curse the first mate who put me on 4 a.m. watch, only to thank God that I get to watch the world be made anew, as if this were the Book of Genesis and God were moving across the face of the waters. To go where literally no one else I’ve ever met has ever been, and never will. To enter an ancient world of sextant and the compass; the bosun and the binnacle and the bilge. Of way, hey, up she rises by the light of the Southern Cross.

Why do I do it? The reason I sail is why most people travel. Because of the terror, and the joy, of leaving the known and passing into the unknown; the idea that what you mind find might be better than what you left behind. It might be uncomfortable; it might be scary; it will certainly be un-perfect. But it will be magnificent.

For me, the sea is the eternal unknown; it’s the question I will be asking myself for the rest of the life. The far-off shore I’ll always be pointing my rudder toward, even if the journey is all I’ll ever find.

“Don’t look at the wheel,” the captain told me one night as I stood at the helm in the North Atlantic, and he’d noticed the topgallant luffing as I struggled to stay on course. “Choose a star and steer by it.”

“But which one?” I asked desperately, feeling that ancient anxiety bubbling up within me. “What if I’m wrong?”

“Any one. You have good instincts. Trust them.”

And I put my hands on the wheel.

[divider]Guest Contributor[/divider]

IMG_4491Claire Shefchik is a travel writer whose memoir, Princess of Pirates: How I Ran Away to Sea is forthcoming in 2016 from Cleis Press/Viva Editions. She holds an MFA in writing from Sarah Lawrence College, and has been featured in The Huffington Post, Matador Network, CosmopolitanThought Catalog, and Rain Taxi Review of Books. She blogs at Princess of Pirates.