Confessions of a Part-Time Pirate

By Milledge Webb

My first Friday sunset cruise was tied snugly back to the dock at the city marina and the last smiling customer was helped back onto land. The crew smirked and pointed down the companionway into the dark recesses of the hold.

“Costume time rookie, down you goes.”

“Costumes?” I began to wonder just what kind of boat this was; it must be true what they say about sailors.

“Time to get pirated up.”

And they swung around the cabin like Peter Pan’s Lost Boys, struggling into costumes either several sizes too large or too small. They gave me a pair of what appeared to be extra large candy striped culottes and half of a Robin Hood shirt. A twisted bandanna tied around my head completed the ensemble.

I looked a lot more like one of the back-up dancers in a LoverBoy video than a pirate. We loaded up and set off into the darkness, swashbuckling to sea-shanties on CD.

I have been doing this for more than two years now. I never had a job that I liked this much. I have come to peace with dressing like a pirate. It’s really not that bad, except that my mom and dad only tell people about the pirate part of my job.

Sample my Mom to another Mom in the line at Publix:

My Mom: So how is your boy doing?

Another Mom: He just finished law school. How is your son?

My Mom: Well, he’s still working on that Pirate ship.

They never mention that we sail a 72’ foot schooner the old-fashioned way, all weak minds and strong backs and regular beatings. No sir, all they remember is pirates.

I suppose it’s inevitable.

St. Augustine attracts a special breed of weirdo, the Pirato-file. These are the people who have normal jobs at the power company or whatever and then go home, dress up like Captain Hook and talk like him, too. Their wives cram themselves into corsets and bustiers while trying to talk like sea-hags. Renaissance fair regulars look at these folks and shudder, “Weirdoes.”

I am not one of these people.

Each night I put on my pirate costume while silently repeating, “At least I’m not working at T.G.I. Friday’s.” And then I tie on my bandana and smile.

It is a normal Friday night on deck and I stare out across the river, and try to look as cool as I possibly can while wearing my costume. I help families in matching T-shirts onboard and hoist their kids high and set them down on the deck. The kids ask if I’m a real pirate. I smile and give them a big “Yarrr,” because after all I’m as real a pirate as they have ever seen.

I start rambling from family to family, telling jokes and asking where they are from. I make it a point to Google places I don’t know about, like Missouri and Connecticut, carefully cataloguing facts and sports team names so that I can find common ground and have something to chat about while I serve Diet Cokes and bottled water. I dig it, because you get to meet all sorts of folks, and they all seem to be bananas for everything pirate.

A group of drunken, single girls out on the town oozes with possibility. Make it a group of 40-something recent divorcees with vodka breath and plastic swords and it oozes something else. A group of these walked on my deck one night, looking at me with disappointment when I help them aboard and they squawk about how they where expecting Johnny Depp. I seat them along the port side of the boat, next to the coolers. They giggle at my accent, “Sorry, Hun. Weah from New Yawk.” I smile and lean against the rail. If you can’t beat ‘em, charm ‘em; it’s the Schooner Freedom way.

I turn on my sugariest, sweet tea Carolina accent and work the group. The whole “Yea, I love this job; where else could I get to dress up like a pirate and get paid for it” shtick. By the time I bust out a few “Ma’ams and Ya’lls” I have them eating out of my hand. Or, so I think.

We raise the sails and they turn from the mildly annoying Long Island peanut gallery to Step Moms Gone Wild with a splash of chardonnay. Usually our customers are here for an hour of ghost stories before their kids fall asleep in the mini-van on the way back to the hotel. Not the Step Moms. They are having quite a time, and they like the attention. They also know my name. Right in the middle of a pretty good story about a ghost with no head, their glasses are empty. I hear them calling me and giggling, holding their cups up so I can see. I am busy adjusting a line, and they think I am ignoring them. The Chardonnay mutiny begins. I hustle with the lines and rush to their aid, hoping to quiet them down. But they are just getting wound up.

The other customers shoot dirty looks down the port side and pleading looks at me. I try to be charming.

“Ladies, can you please keep it down.”

That only makes them louder.

Then from the stern “the Captain needs you to keep it down.”

Now they are really fired up. I often wonder if they would behave this way in front of their children. I could only imagine how some 19-year-old frat guy from Rutgers would react to his mom misbehaving this way in public. I bite my lip and ask them again to keep it low, so that the other customers can hear the stories, Hell, even I wouldn’t mind hearing them right now. Even the actor who tells the stories is getting a little steamed. He puts his hands on his sword and pistol and tries to look authoritative. The Step Moms are oblivious, and I do my best to placate them. They submit by loudly whispering during the stories and harassing me every time I pass them.

My decision to seat them dead center in front of the coolers was a poor one. I have to bend over in front of them every time I need a Bud Light or a Diet Coke, so I take to squatting instead of bending to avoid their “busy hands.”

We come about under slack sails and things have gone from bad to worse on the port side. The no smoking rule has become quite an issue with Step Mom Gone Wild #3. She has a Capri 120 tightly clenched between her teeth and mocks me by flicking a Bic lighter. I go through the prepared smoking policy speech.

“Gunpowder, Coast Guard, Captain says so…” She takes this as a personal challenge and flicks the lighter closer and closer to the tip of her spaghetti thin cigarette, daring me to do something about it.

In the 20 minutes left before we finally parted ways, the Step Moms did everything in their power to mess with me. I did my best to just ignore it and focus on the other passengers, who were also trying to ignore them.

When we open the Bridge of Lions for the sixth time that day, matters come to a head. I forget myself in a rush to serve a small boy a Sprite before we strike sails and foolishly bend over right in front of them. I won’t tell you where they poked me with their plastic swords, but it brought back bad memories of sports physicals and summer camp.

I jump like a hooked tarpon and the Sprite slips overboard with a hollow splash. Now is one of those deep-breaths-find-a-happy-place moments. I do just that and carry myself away to anywhere but here, anywhere but within plastic sword poking distance of the Step Moms.

We strike sails and tie her to the dock, and I hide my anger and discomfort in a place only people in the service industry know about. That hollow spot that we stuff full with every shift of rude comments and complaints. Then we smile and keep on moving.

The Step Moms have not forgotten, and they wave their plastic swords at me and giggle. I hold my chin high and pose for a picture with them. It takes a big man to smile for the camera after being on the receiving end of a plastic sword yucky touch.

I wonder if Johnny Depp ever has nights like this.