It’s evening in late February and I’m at home listening to the howling wind. I pace the house, driving the family a bit crazy. As my departure time gets closer, I get the chart and spread it on the dining room table, using jigs and sinkers to lay it flat. With my finger, I trace the direction of both the wind and swell. “This will not be pretty,” I say out loud.

I run a pilot boat on Block Island Sound. This evening we have an outbound ship arriving from New Haven, Connecticut. My job is to get the pilot off the ship so he doesn’t end up taking a ride to Singapore. We meet the ships between Block Island and Point Judith, Rhode Island. In weather, this maneuver can get hairy. We want the ship to act like a jetty so the pilot can descend the ladder in the lee. It may sound simple, but the wind and sea rarely work in our favor.

The question I always ask before heading to work is: What’s the weather doing now? On this February evening my local weather facts are as follows: west wind 38 knots; south swell 8 feet every 10 seconds. I use the Block Island airport and Buzzards Bay Tower for wind, and the sea buoy southeast of Block Island for wave information. I know I won’t see these exact conditions, but the data provides a good ballpark. I plot the wind and swell directions on the chart. From there I’m able to plot the approximate course for the ship. Plotting may seem like overkill, but it makes me feel more confident. When there’s weather at sea, the more I know ahead of time, the better I feel.

An hour later, I’m at the dock in Snug Harbor, where the wind screams. I can see Point Judith and observe that most of the fishing fleet has come in for the blow. I take the boat off the dock, then pass Snug Harbor and Dog Beach. At night everything is magnified—the wind feels like a tempest and the night looks darker. We pass through the harbor entrance, George’s restaurant on my port side. This is where I start to feel the ocean, the mood of it. “This won’t be pretty,” I repeat. And the mate agrees.

We feel the surge, a precursor of things to come. At the West Gap—the link between Point Judith and Block Island Sound—we hit our first sea. The mate and I have our same conversation. “It’ll get better a mile out.” Sometimes we’re right, sometimes we’re not. Outside the wheelhouse, the wind and sea have come to life and I begin to relax. I trust the boat, the hull and myself.

Running the pilot boat has, in a way, impacted the way I run my own 21-foot Contender center console. The 64-foot pilot boat, by the sheer number of trips I do in all types of weather, has given me the confidence to run in fog and wind in my own boat, because when it comes to boat handling, there is no substitute for repetition.

I used to hate docking. I’d get so nervous. It was the same when running at night. I hit docks and pilings and ran boats timidly in the dark. Then something happened. I got better at it.

I don’t think you can learn how to drive a boat by studying a diagram. I believe in making the mistakes. That’s how you grow. I make one almost every week. I come into the ships too fast or too slow. I slam the sides of tankers so hard that my teeth crack. I run a following sea at the wrong angle. To counter those mistakes I try, at a minimum, to get the weather down. That’s why, when I’m not on the job and preparing to run my Contender across to Block at night in fog, I make it my business to know current and wind.

Once we’re clear of the Gap, I put the boat on course and find the ship on radar. It’s too sloppy to sit, so I stand, slowing the speed to 7 knots. The west seas are what I thought they’d be: staccato and steep as cement walls. As we get away from land the south swell really shows itself, trying to raise my port side as the west seas continue to drive at my bow.

This is the Block Island Sound washing machine, its signature move. All you can do is hold on. But even this is what we thought it would be. I turn the spotlight on to gauge the wave directions, which can be hard to do. Waves are rarely uniform, rarely patterned.

On the radio I talk to the pilot. We have the ladder on the ship’s port side. We agree on the ship course of 110 degrees. I run alongside the ship, matching its 8-knot speed. At night in weather, this maneuver never looks great. These ships are big, and the ocean is bigger. It’s unforgiving. And yet, we get the pilot aboard.

“Not nice out,” the pilot says as he comes into the wheelhouse. We start to leave the lee side of the ship. This is where I have taken some of my biggest rolls, the kind that make every muscle in your body tighten like a bow string.

“Hold on,” I say. That phrase is repeated constantly on the boat. As I get ready to turn for Point Judith, a wave comes at us fast, moving as if it’s not attached to the ocean. “Hold on,” I yell.

We rise up and fall off, and keep falling. Then a big west-running chop grabs our stern and twists us hard to starboard. That’s when I hear a scream behind me. “My leg,” moans the mate.

After a few minutes the mate says his leg is not broken. He can move it. It seems that during the roll, the pilot had lost his grip and tumbled across the wheelhouse, slamming into the mate who was wedged into the navigation table.

In the end we are all fine. I give the helm to the mate and he takes the boat in, the west wind on the port quarter, south swell on the starboard beam. Just like we figured it would be. 

This article was originally published in the May 2021 issue.