The Easiest Way To Win A Bunch Of Free Vacations

Just show up on a Tuesday night and hope nobody else does!

Welcome to CHAPTER FOUR of my island memoirs, originally published in 2011 and adapted to include current times and life situations. Each chapter is free to read for the first week and then it’ll drop behind a paywall. Coconuts are free…rum is not 🍹

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Want to know a great way to get to Jamaica?

WIN A TRIP!

What’s even better than winning a trip? How about winning TWO trips?!

It’s pure madness, I tell ya! Nobody should’ve been as lucky as I was, and I never have been again since winning two vacations within a three-year span.

It’s almost as if those “Kristi needs to be in Jamaica” gods feel a need to secure their five minutes of fame in every chapter of my story.

Rewind to March 2003, when I won my very first trip. At that point in my life, I’d never travelled anywhere and knew nothing about Jamaica except for the music. Can you imagine transitioning from that to having a Jamaican flag tattooed on my arm within a few short years?

Let’s talk about July 2006 now. A local nightclub here in Calgary was giving away a trip to Jamaica. This time, it was for the massive annual music event called Reggae Sumfest in Montego Bay.

A friend of mine alerted me to the contest and said she heard there was a rule that you had to be present at the nightclub to win.

Only a true destination addict (or a total loser) would go to a nightclub alone on a Tuesday night, fill out roughly 10 ballots, and then hang out like a wallflower waiting to win a trip.

I sat there, bored out of my tree because the draw didn’t take place until midnight. Funny enough, I bumped into the promoters of the first trip I’d won, and wouldn’t you know it - they were giving away this trip, too. I remember them saying, "Wouldn’t it be crazy if you won again? How fun would it be to bring you back to Jamaica!”

About 45 minutes later, that comment took on a whole new meaning.

When it came time for them to go on stage and make the draw, they announced the winning name…

Ashley Finster!

Sadly, my name is Kristi.

My heart sank, but only for the five minutes they waited for Ashley to grace us with her presence. She was a no-show, and the crowd began yelling for a re-draw.

They drew again. Guess whose name was pulled???

Yup…Ashley Finster again. Can you imagine?