[A lot of people are still wondering what this Pirate of the Year thing is all about, so we’ve asked an expert to write about her experiences. Mateys, welcome reigning Pirate of the Year Finn Reed to tell you about what she had to go through to win the award. The challenges you will face this year will probably be different than the ones she overcame, but you’ll still find this useful! –Phillip]

Finn Reed - 2016

Finn Reed, Pirate of the Year 2016

So you want to be pirate of the year? Well, step up lads and lassies alike because with these tips you’ll be well on your way to being a swashbuckling master. If you’ve never heard of Pirate of the Year, it is an esteemed title which, if earned, will win you a shiny trophy and, of course above all, bragging rights. But with all the scurvy sea-dogs out there how can you be certain to reign supreme? Some would say you simply need to be at the right place at the right time; which in this case is somewhat true as you’ll need to make port at the Tim Faulkner Art Gallery to attend the Kentucky Pirate Fest! There, the Pirate of the Year 2018 will be crowned, and it could be you!

So how can you secure your spot as this year’s premier pirate? You’ll need to complete grand tasks against your fellow scallywags in an array of appropriately pirate-y challenges such as walking like a pirate, seducing like a pirate and giving commands like a captain to name just a few choices that might be assigned by the judges! (Full disclaimer: the tasks will be picked at random and might not be discussed in this guide, but I guarantee you’ll find at least one of these tips from my personal experience helpful for any challenge thrown at you!) After each challenge you compete in the number of contestants will be decreased, so how do you make the cut?

Walking like a pirate might seem to be the easiest but don’t fall into a trap! Many contestants will portray the classic drunken pirate (a tribute to the great Captain Jack Sparrow), but that can become old as one after another pirates do the same gag. Not to say you can’t do it too, but do something to spice it up; interact with an audience member or a fellow contestant, make a joke, do a flip (maybe not if you’re intoxicated, no one wants to do the paperwork). You want to get picked for the next rounds so don’t forget that the greatest way to be remembered is to do something unique!

Seducing like a pirate is the trickiest challenge unless you’re simply a full-time Casanova with endless charm and charisma. But don’t be discouraged, this challenge can be very fun! If you’re feeling daring go for the full-on seductive winks and whatever else might be in your arsenal—maybe you took a belly dancing class in college? Even if you’re not able to make the burley lady or the lovely man swoon, you can at least make them laugh! Pirate themed pickup lines are always a good choice, perhaps one about how a certain lovely lady puts a shiver in your timber…

Now that you’ve made it through the first two challenges, it’s time for your final task—give commands like a captain. Remember our old friend Jack? Now’s the time you want to break him back out. Captain Jack Sparrow has an arsenal full of great commands to—well, I was going to say borrow but considering you’re being as pirate-y as possible, we’ll go with “steal”. Nonetheless, for this challenge it’s not a bad idea to pick a couple of naval phases to throw into your commands to make you seem like a true old salt of the sea! Perhaps “avast,” “hornswoggle,” and “freebooter” would all be good choices to add to your vocabulary. Think like a true pirate here: what would you want your captain to give you? A raise? Rum? Port every week in Tortuga? The options are endless…

These tasks are just a few that you might find yourself up against, but you may be faced with surprising challenges as well. Above anything else have fun as you compete for your title! If you’re enjoying yourself, you’ll find other people enjoy you too, which might just be the determining factor in your victory!  The best advice that I believe can be given from one Pirate of the Year to the next is not to take yourself too seriously. Don’t worry about messing up or embarrassing yourself! After all, to err is human but to arr is pirate!

Best of Luck,
Pirate of the Year 2016, Finn Reed