Editorial: Lose the Pirate Flag

pirate-pics-2 The editors here at Terrapin Tales generally follow the Fun Boat Manifesto: as long as it’s fun, and doesn’t harm anyone else, go for it. But we haven’t been on the water as much as we should lately, and maybe that’s what’s making us a bit cranky. Aside from being irked by large motor boat wakes, which we’ll get to in a later editorial, we’re here to state that we’re firmly against pirate flags, except on actual pirate ships. 

Pirates these days fall into one of two camps: scary pirates from countries undergoing strife or civil war, and paunchy middle aged folks who bought a boat and decided that affixing a black and white flag to their rigging would add just the right touch of rebellious attitude – like slapping a Harley sticker on a Winnebago. We feel sorry that geopolitical forces have forced the first camp to resort to violence for survival, but at least we understand their predicament.

The second group tends to have no economic hardship, aside from paying for their slip and their children’s higher education costs. So why the flag? A pirate flag on a boat is not the sign of a good seaman, a fun boat, or a world cruiser. It says one thing: I’m middle aged, and I don’t know how to create my own adventures anymore.

If you’re truly looking for excitement, the editors have a few recommendations: rather than installing a pirate flag, skipper, sell your over-large boat for something smaller and tippier: perhaps a Laser or an open-water rowing shell. Both will test your balancing skills, get you physically fit, and put you more in touch with the water than a tubby yacht. A small craft will be lively, exciting, and perhaps damp- but nobody said that being a pirate was going to be dry.

pirate-pics-1-3 If you’re unwilling to go with a smaller boat (that we’re certain you’ll use more than your big toy), we recommend that you make your own flag. Given the long tradition of semaphore and flags in maritime culture, this would be a keen way to learn something new and impress your yacht club, or at least your mate.

If you’re like most people flying a pirate flag, you probably aren’t sailing during the winter cold (though real pirates wouldn’t let a little unpleasant weather stop them) So you should have plenty of time to pull out the old sewing machine (or acquire one- another exciting opportunity) and get started.

Better, make a few flags and give them away to fellow boaters as initiation presents for your new secret adventure club. Don’t divulge the meaning of whatever obscure symbol you choose—unless you’re offered some good grog. Go on some kind of sailing expedition to waters you’ve never ventured into before, even if that’s just an overnight cruise beyond your day sailing grounds. After that, plan another cruise—this time at night, when the chance of adventure increases tenfold.


We’re guessing historic pirates were good seamen, able to overtake other vessels under sail power alone, and smart enough to reach their destinations solely with traditional navigational tools. So, while you’re improving your piratical skills, how about turning off the electronics and steering with just a map and compass?

Whatever you do, we hope that once you ditch the pirate flag, you’ll make skill-building, risk, and challenge part of your life in 2017. Happy sailing.


  1. Amen! Down with the Hollywood revisionist history “pirates” It was once a hanging offence just to sail under a black flag.

  2. I’ve been known to sail under a pirate flag, the middle-aged hopefully not too paunchy one, but I sail one of those small tippy boats, one that isn’t even 12ft long. Years ago, while building my SCAMP, two of my cohorts and I were tailgating after “work” and one of the instructors walked by and said we were a bunch of pirates. Well, I found three pirate flags and we flew them the rest of class. We were/are firmly in the let’s-find-some-small-boat-adventure type of pirates, no pillaging allowed. Of course, it’s hard to look mean in a 12ft boat that looks like a bath toy 🙂

    We did cross wakes with a very admirable fellow who didn’t take kindly to our flags since he actually did deal with real pirates – of the Yemeni type. He from the bridge of a bristling warship. This gave me pause, I certainly don’t want my Huck Finn style adventures identified in any way as one of the other type. I wondered for a while what other fun-loving, yet a little rambunctious name we could sail under. I decided on “Hooligans”. Although the dictionary defines it as a “cruel, brutal man”, but I always thought of it as fun loving, yet a little mischievous, doing the kind of acts like re-arranging the letters on a sandwich board in a funny way, or wielding a water gun on a hot summer day. I even commissioned a whimsical flag design, but have yet to sew it up.

    I think us small boaters need a flag to fly under, one that promotes the fun and adventure you espouse. Flag or no flag, getting out on the water is the name of the game.


  3. Fun loving yet a little rambunctious used to just describe sailors on shore. So with the cunning use of a flag do you think we can inspire a fleet of adventures? I see small flags planted all over, proclaiming this beach claimed in the name of….? Sail and Oar League? Huck Finn Adventurers? Bob? Need some sort of artwork.

  4. As a living history Pyrate who is middle aged but not paunchy, I sail with a crew under the Black Flag. We educate people about what it was like for not just Pyrayes but most Seaman in the 18th century. We dress the part with real weapons and fire real cannon. We are more than fit sailing period correct boats! I am a bit put off by the fat shaming sound of your article as well as your throwing people in to two camps who fly the flag. Not everyone falls in to your profiling. Come see us sometime and learn abit about careening and traditional practical sail. As for adventures, we more than have and tale you on them. Look us up, promise we won’t plunder you.😉

  5. Whilst pirate flags are flown in the UK by mainly over 50s it is always for the benefit of their grandchildren 🙂

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