the first crossing

the one where he sails out to sea, contemplates death, then decides to enjoy himself anyway

We are out at sea.

Claire leans on the tiller, trying to surf the 8-foot waves that seem to come from every angle. Occasionally, one breaks over our beam and tosses the sailboat sideways. The crew brace for impact. Two miles ago, a wave caught us at just the right angle. Water flooded in through our open companionway, soaking our living quarters down below. Since then we’ve kept the dropboards down.

“It’s starting to ease up,” Claire says. “Let’s switch to the autohelm.”

What a relief.

We set sail from Chaguaramas three hours ago. An hour and a half after that, we ran out of daylight. Now we bob along—a single pin-prick light below a sky glittering with stars. Behind us is Boca de Monos, the turbulent gateway between Trinidad and the Eastern Caribbean. Ahead of us is 70 miles of ocean to Grenada.

After a bit of fiddling and some light swearing, I manage to install the autopilot. Its mechanical arm buzzes cheerily, holding our course.

For the first time since we left the safety of the marina, I pause. I lock eyes with Claire, and immediately she knows

I am convinced we’re going to die.

Remember that propeller you installed yourself? How are you so sure it won’t just fall off?

What about your rudder? It sure would be a shame if you lost steering. With a roaring current pushing you into the nothing out West.

One poorly placed wire can become an arc welder if it shorts against the engine block. If the smoke didn’t make you abandon ship, you’d surely be fucked without propulsion.

I’m in a total unreasonable panic. With every passing second, I fight the urge to turn our boat around.

“I’m going to do a systems check,” I say.

I make my way down below where I rack my brain for the unlikeliest catastrophic situations and proceed to inspect every inch of our vessel for signs of our impending doom.

Bilges. Clear. Alternator. Working. Through-hulls. Dry.

Everything looks to be in order. But that’s what the boat wants me to think! It’s only a matter of time before shit hits the fan.

GPS. Fine. Keel bolts. Still attached.

If everything is so fine then why, pray tell, do I feel like I’ve been shooting adrenaline? Get a hold of yourself! For God’s sake—nothing is happening.

Nav Lights. On. Check the weather. The weather…

5 hours have passed. I’ve been so busy fretting that I didn’t notice it. But now something catches my attention.

The stars are gone.

That rhinestone blanket above has turned deep black. It’s dark in all directions.

Suddenly the wind picks up, shaking every loose bit of canvas in a deafening din.

We’re going faster. The boat keels towards the water. Frothy spray comes over the bow. This ride has just kicked into a higher gear.

And then comes the rain.

“What if we run into pirates?”

“We’re not going to run into pirates.”

“How do you know?” (i don’t)

“Because we’re sailing at night. They’re not around at night.” (am i bullshitting?)

“But then we sail in the dark? How do we make sure we don’t run into anyone?”

“We’ll have our lights on.” (i’m totally bullshitting)

“But they won’t have their lights on. You just told me people turn off their lights to hide from the pirates.” (they do)

“We won’t turn off ours so they’ll see us.”

“But then the pirates.”

“They won’t be around—”

“If they aren’t around then why do people turn off their lights?” (oh, to hell with it)

“I don’t know.”

It’s two days until the crossing. Claire and I are hunched over a map. I’m pushing triangles around talking about “degrees of set” and “flood and ebb currents”, but really it’s all dancing around the question that matters.

Will we get there safely?

“Let me walk you through the route again.” I say, “If current is 1.5 kts…”

As I prattle on, my mind begins to wander.


I snap to.

“Sam, you’ve already walked me through this. The current, the timeline, all of it. We’re ready.”

“I…honestly, I don’t feel ready,” I say.

Claire smiles, “You’ve planned this trip down to the minute. What’s left to do?”

“I don’t know. I feel like I’m flying blind here.”

That makes her laugh. “I wouldn’t expect any different. You worry. It’s why you get to the airport four hours before your flight. It’s why you’re wracked with anxiety when you’re double parked. It’s just who you are. But you know what, I don’t worry. I know you’ve done your best to keep us safe. It will be enough.”

She pauses, then adds, “This trip is going to be amazing, just you wait.”

A squall.

Warm air rises faster than it can be cooled, forming tall, dark clouds. When the weight of all that moisture becomes too much to bear, it comes down in a violent shower.

“I’m pretty happy we put two reefs in!” I call out to Claire. Both of us are completely soaked.

Claire nods. A reef shortens the sail. Less sail area means less speed. Two might be considered excessive, but we’d studied the passage weather for weeks and knew that a nighttime squall could put us on our heels. In a blow like this, those reefs keep the boat upright.

Far from being overpowered—L’Apéro is performing. The rain has pounded the seas flat. She cuts through the water at nearly twice her previous speed. It’s all starting to feel rather exhilarating.

I sheet out the main—the sail’s belly bulges just ahead of her midway point. Our speed creeps up.

Claire shoots me a look.

“It would be a shame to waste this breeze,” I say.

She smiles, “You’re thriving, Marfleet.”

Good God, she’s right.

Here we are, flying kites over a plastic bathtub, in the pouring rain, in the middle of the Caribbean Sea, and I’m thinking about going faster.

I think I might be starting to enjoy myself.

Look ahead, do you see that light? Port side bow.” I gesture towards a steady glow on the horizon. “It hasn’t moved in the last hour. And the color looks to be more yellow than white. That’s the oil rig.”

A quick check of the GPS confirms it. We’re about to pass through Hibiscus Gas Field—our only landmark between Trinidad and Grenada.

Claire beams, “We’re right where we need to be.”

It’s one thing to plan a trip on paper. It’s quite another to see confirmation on the horizon, after hours of muddling in the dark. We might not be totally out of our depth out here in the ocean.

“Sam, you should let Chris take over. Get some sleep.”

The distant glow of the rig is coming into focus. The rain has stopped as suddenly as it came. All around us glow the lights of tankers, supply vessels, other denizens of the sea.

What about electrical fires? Collisions at night? Maydays and SOSs?

I push those thoughts aside. We are as prepared as we need to be. There was a time for worry, now there’s nothing more to do than to take the ride.

Chris emerges from the living quarters—bright eyed and characteristically unconcerned.

“Ready to go under, bud? I’ve got it from here.”

Actually, I am.

We reached Grenada after 22 hours.

The passage held more excitement. There were even larger squalls. Passing tankers. Large patches of seaweed that tried to jam our propeller. But none of it felt existential. Nothing held the weight that the first squall did.

Reflecting on the lessons of the passage, I’m still the same person. I will get anxious over boat maneuvers. And I’ll still plan every sail like it’s a grand battle. But I see now that my fear isn’t a signal that I’m doing something I shouldn’t do. It’s a guide that shows me how to do a meaningful thing the right way.