First Passage


In early May this year, I found myself unemployed – just barely recovered from the shell shock of working at one of the best and worst jobs of my entire career. I was leaving the gym, headed home for a much needed shower, when the phone rang. It was Jamie and Niki – the sweet couple who sold their house to Nick and me back in October.

They were about to buy a 40-foot catamaran, which happened to be located in the Caribbean on an island I’d never heard of before, and could I drop everything and help them sail it back to the United States?

My heart skipped a beat at the thought of participating in such a big adventure. I had raced dinghies and the odd keelboat for about 15 years. And I’d always wanted to try sailing a long distance. I’d just never had the opportunity. The pull of the wild unknown made me say yes immediately.

Adventure and doubt are twin siblings, though. Immediately after agreeing to join them, I questioned the wisdom of their invitation. It had been more than a decade since I stepped foot in a sailboat, and I’d never made an open water passage. We’re they sure they wanted me along? Jamie and Niki assured me that my ability to sail, tough as nails attitude, and tolerance for temporary misery (gained from more than a decade of climbing mountains) were adequate qualifications and made up for my lack of experience.

A full life does not come from giving into doubt, so I silenced further fears, bought a one-way plane ticket and a pair of new sailing gloves, and began pulling out of commitments that would prevent me from being gone for a month.

It is not hyperbole to say that flying into SXM is one of the most spectacular landings in the world. The airport is located on a small spit of land – with water nearly kissing three sides of the runway. The prevailing trade winds mean that planes must approach from the west over open water. This, in and of itself, is not all that unusual. (Planes landing at SFO, for example, frequently approach over water.) The thrill that comes from watching the belly of a 737 skim the ocean’s whitecaps rises tenfold, however, as the engines surge and the plane soars past a beach full of people, who are so close they risk being blown over by the plane’s jet wash. With my heart in my throat, I added my own voice to the symphony of gasps and shrieks of glee.


Niki picked me up at the airport and we headed to the boat where we found Jamie (aka Captain Crabby) exhaling a purple stream of profanity over the non-working AIS – the system that would help us identify and avoid other boats underway. He never could get it working, so we vowed make the most of i360 – our visual backup system.

I didn’t have time to wonder what else might not be working on the boat, because Jamie and Niki wanted to be under way the next day. Given that most people spend months outfitting and retrofitting their boats for long voyages, and these two had been working on her for only a few days, I was pretty sure we’d find out soon enough.

On Wednesday morning we pushed off the dock and wove between the boats anchored in the harbor and out into the lazy rollers of the Caribbean Sea. For better or worse, Niki, Jamie and I would be no more than 40 feet from each other for the next three weeks.

I felt a new kind of freedom. A recklessness of abandoning myself to the ocean.

It was time for my first night watch. Jamie stood by my side, lit by the glow of the fading sunset. “It’s easy,” he said. “Let the auto pilot keep the boat pointing at 250 degrees. And make sure we don’t hit anything. I’ll see you in a few hours.” I cinched up my harness, clipped in to the starboard jack line, and tried not to think about the consequences of falling overboard at night when everyone else was asleep.

I perched myself in the captain’s chair. My eyes gradually adjusted to the growing darkness, and I looked up with sincere appreciation. The stars! A planetarium of stars! The night sky wasn’t black, but shot through with pinpricks of cold white light. The milky way was as clear as a strip of cloud. It was really happening – this dream come true!

The next morning the wind had risen to 25 knots; the sea giving the wild sensation of sailing in midair as each swell rolled underneath us. The hazy strip of Puerto Rico off to our right. Nothing but a flat blue horizon in every other direction. It was unlike any landscape I had ever experienced. I stood at the bow with my mouth hanging open. Jamie chuckled knowingly.

For the next week we would be at least 60 miles from the nearest land mass. The wildness of the open water gripped me. We were walled off from civilization by sheer distance. Out here pirates could take over our boat, and no one would ever know. (Side note: Jamie says Pirates of the Caribbean aren’t really a thing, just a Disney creation.)

Danger was also present in more intimate ways. With each violent pitch and yaw, I was quickly and painfully learning the edges of the boat. I stubbed my toes hourly on hatch covers, stairs, cleats, and other things that seemed to materialize spontaneously. The bruises on my arms and legs had bruises.

One morning I decided to cook a veggie hash and scrambled eggs for breakfast. Food had the curious effect of settling my stomach, and I was damned if I was going to let a little rolling get in the way of a gourmet breakfast. I went to the galley and tried to prepare the peppers, onions, and potatoes. I needed one hand to keep the pan on the stove and two hands to chop. Eventually, I figured out a way to prop myself between the stove and counter to free up both hands to cook. I tried to pour myself a cup of tea and the hot water streamed out of the kettle sideways onto my bare knuckles. I moved toward the sink to douse my hand in cool sea water, and the chopped vegetables flew off the countertop like a swarm of angry wasps before scattering on the floor. I tried to dribble a bit of olive oil in the pan. At first, the oil refused to come out. Then gravity switched and half the bottle glugged out. An hour later, we laughed together and ate piping hot fried potatoes and scrambled eggs. Difficulties momentarily forgotten.

Rough seas continued for the next few days. It wasn’t a storm. The skies were sunny. But high winds and swells continued to strain the boat and our nerves. The boat would rise up on the crest of a wave and plunge wildly into the next trough. We would whoop and howl, sure that we were surfing our 40 foot home away from home. Our entire existance was crusted with salt. Every gust of wind blew us further into the unknown.

At night when I wasn’t on watch, I would lay sticky on my bed, in the stifling heat and humidity. From somewhere came wooshing, waterlogged, gravity-defying dreams.

Then one day I gazed at the horizon. A huge island loomed like a mirage. Jamaica.


A few days later, rested and restocked, we settled into a kind of restless routine. The sea was calmer. Gloriously calm, actually. The high tropical sun baked the waves as we glided north on the current that that runs in the narrow passage between Cuba and the Yucatan Peninsula. Humidity left dripping patches on the walls.

As I sat, steaming in the tropical air, feeling the texture of every swell, I came to understand the meaning of cabin fever. With more than 500 uninterrupted miles to go, I got itchy. Not like scratchy itchy. Just this really strong desire to move around. To use my muscles to wake me up. Alas, there was still a week or more left in our passage…I just had to figure out some way to deal with it.

We landed a 24 pound mahi mahi and prepared a simple yet undeniably elegant sushi dinner – complete with seasoned sticky rice, wasabi paste and soy sauce.

We piped our favorite tunes though the boat’s speakers and had our first rum-punch-fueled dance party. Niki and I played our ukuleles and wrote songs memorializing our adventures.

Later, we lay on deck, watching the dolphins ride our bow wave and leap in flashes of grey through the air – mere inches in front of us.

The boat had become home. I felt in step with its rhythms. I liked the nights, the sunsets, and the lights of passing ships swinging through my cabin’s port hole.

The dangers and miseries and sleepless nights lodged in the back of my brain, as stories that smacked of adventure. It’s incredible how I had grown accustomed to this life.

This is what real adventure does. Not only does it explode our notion of what is possible. It redefines our notions of what is easy and can accept as normal.

At 2:45 am, I woke for my scheduled night watch. This time the boat was curiously quiet. On deck, the bright lights of Gulfport, Mississippi blinded me. Twenty three days and 2000 miles after leaving Sint Maarten, we had arrived in the United States at last. Before reporting to customs and immigration we savored a last sunrise sashimi breakfast made with wahoo we’d miraculously caught the night before and watched a pod of dolphins slide lazily past our stern.

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