Anyone who’s serious about getting a bigger boat should consult sooner, not later, with someone who did that recently.

Someone like my fishing buddy Headwind, who this month observes the one-year anniversary of his own upsizing.

“Observes? Why not say celebrates?” Headwind just said. He’s the only one allowed to look over my shoulder.

“Because I fish with you,” I told him. “Because I ride in your truck with the boat behind us and launch and haul it with you. Because I’ve watched you getting used to the boat the hard way—stomping and hollering as you go.

“If you spoke to your wife and dog that way, they would leave you.”

Headwind said it’s not the new 18-footer that turns on his temper and coarsens his language; it’s the situation—almost everything’s different from the canoe-like 15-footer (plus 4 inches) that still sits in his side yard, its 9.8hp outboard fidgeting in the garage.

When we go a few weeks without using that, Headwind needs to be reminded to tow it around the neighborhood for a mile or two and run the engine on the garden hose for five or ten minutes.

If he doesn’t, the trailer tires will develop flat spots, maybe soft spots. The engine may forget how to run.

The difference between a 15-foot boat and an 18 is something like the difference between a 15-inch fish and an 18-incher: not only more length but also more beam, more bulk, more weight.

More things to do before hitting the road, more when you get home.

If you know Headwind, you know he likes doing things the hard way. That’s why everyone here at the Fish or Cut Bait Society calls him Headwind. Even I forget his real name.

I told him I’m the one who should celebrate, because so far I haven’t had to call an ambulance when he cusses himself to death—hopefully with his new 18-foot skiff still on the trailer, so I won’t have to crank it back up there by myself. That’s a two-man job unless the wind is dead still.

His old boat, a 15-footer plus 4 inches, is an easy one-man launch and haul.

If there’s a crosswind at the dock, one of us has to wade down the ramp to keep the new boat centered over the trailer while the other cranks it up with the winch.

The new rig came underfitted with a 1,200-pound capacity winch—good enough, perhaps, for the hull alone but not with the 216-pound 60hp outboard, 60+ pounds of gas, two batteries, and... everything is bigger, heavier.

The bigger boat required a 2,500-pound capacity winch with two gears, replacing the stock 1,200-pounder. One more size upward wouldn’t be excessive.

Though he’s getting on in years, Headwind can carry the small boat’s electric trolling motor in one hand from the garage to the boat and back. When he called the manufacturer to ask the new one’s weight, he was told it’s 30 pounds. I’m guessing 40. He’s guessing 50.

That trolling motor is a lot more complicated than the other. It has spotlock and autopilot. I should probably read the instructions because Headwind hasn’t had time. As for the GPS—please don’t ask.

The little boat’s little engine weighs 81 pounds and its fuel tank holds 18 pounds of gas. When he acquired it, 12 years ago, Headwind could have hauled that up the trailer without a winch.

Headwind didn’t consider those differences in advance, even when I wondered whether he would be able to launch and haul alone if he had to.

“We’ll figure it out at the ramp,” he said then. A year later, we guess he could do it if there’s a dock.

“There’s a lot more to remember, a lot more to do, a lot more to worry about, when your boat’s 2 feet, 8 inches longer,” he says almost every time we fish.

Headwind’s new boat is not only that much longer; it’s also 21 inches wider. So’s the trailer—76 inches now compared to 66 before. Hitched to his pickup, the whole rig is 43 feet long, front bumper to outboard propeller. The smaller rig is 6 feet shorter.

A few years ago, in neighborhoods we sometimes drive through, various municipalities installed what we call traffic circles. Others call them roundabouts. In the dignified circles (ha!) that Headwind and I frequent, it’s hard to mention them without exposing oneself as a vulgarian.

Let’s take an imaginary ride to the launching ramp. Headwind’s driving. Just ahead lies an intersection that’s too small for the circle inserted in the middle of it.

“Dirty word,” Headwind mutters. “Bumpity thump” go the trailer tires as he makes a tight turn. He could go a little wider, but that would knock the tires against the curb, going “Bangity bang.”

“May the Deity condemn it!” Headwind shouts. That’s as close as I’m allowed to go to what he really says.

Here comes an entry ramp to I-95. A sign says so. Translation: “All hope abandon, ye who enter here.”

We must merge into traffic, so Headwind switches the left turn signal on. Four other drivers instantly cross four traffic lanes, trying to squeeze us onto the shoulder.

When we pull the smaller boat, the others scarcely notice. This new rig is conspicuous.

“With the little boat, we need hardly any more stopping distance than we need without a tow,” Headwind says. “With this one, we need close to 100 feet, even in slow traffic.”

As he speaks, another driver veers into our safety space. Headwind drops back a bit and a second driver jumps in.

“May a thousand deaths befall you!” or something like that, Headwind screams.

“They can’t hear you or see you shaking your fist,” I tell him.

“I can hear them laughing at us,” he tells me.

The navigation system he uses tells us when we should arrive at the ramp, but it doesn’t know we’re towing a boat.

It doesn’t know when we have the little boat either, but that one’s size and weight are nearly negligible.

If the pleasant female voice directing us were a real person, she might be asking why we’re slowing down, why it’s taking so long to speed up, why we don’t move into the three-length opening on our left.

“We’re towing a boat, you idiot!” Headwind would tell her. Sometimes he tells her anyway.

“I don’t understand,” she answers him.

Now we’re about to get into the exit lane. Headwind turns on his blinker, which is widely seen as a sign of weakness in southeast Florida traffic. Someone a few lengths back sees it blink, passes us on our left, cuts in front of us, and stays alongside on our right.

Now we can’t make the ramp without risking our lives or, much worse, Headwind’s new boat. We have to try again at the next exit, then go back.

Headwind flashes his headlights, plays an angry tune on the horn, and calls the other driver a lousy, stinking so-and-so.

The other driver opens his window, sticks his left arm out, and gives Headwind the finger.

“He heard me!” Headwind hollers joyfully.

He told me that towing the little boat has no discernible effect on his truck’s gas mileage. With or without, it’s about 18 miles per gallon. With the new rig, it’s 12 and a half.

So, I mentioned, buying a bigger boat not only made everything harder, it’s also more expensive. As someone who likes to do things the hard way, you should be glad.

“In all honesty,” Headwind confessed, “I am.”

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