Win a Trip To Jamaica!

Want to know a great way to get to Jamaica?  WIN A TRIP!  What’s even better than winning a trip is winning TWO trips! I confess, that’s how all my Jamaica madness started 6 years ago.  In fact the 6 year anniversary of my first trip is coming up in March.

Rewind to March 2003, about 6:30am when I heard a cue to call on the Vibe 98.5 radio station, to get your name entered in a contest to see Sean Paul live in Negril. At this point in my life I’d never traveled anywhere and knew nothing about Jamaica except for the music. Imagine that…now I’m blogging about it and have a Jamaican flag tattooed on my arm!

That first trip was fabulous but only a short 5 days – pretty much a teaser.  The whole thing was scheduled and they had us at a big, fat, all-inclusive resort.  Needless to say we didn’t experience any Jamaican culture except what kind of blender drinks they could whip up at the bar and how to double-fist them 24-7.  I left Jamaica happy but dissatisfied.  So unbelievably, for someone who never travels, I was on a plane back to Jamaica two months later.  And I didn’t even go near a hotel!  I stayed in the home of a Jamaican police officer and got some culture shock! I loved it!

I returned again 11 months later with my son, who was 11 at the time.

Now fast forward to July 2006 when a local nightclub here in Calgary also happened to be giving away a trip to Jamaica. This time it was for Reggae Sumfest in Montego Bay.  A friend of mine told me about the contest and that you had to be present at the nightclub to win so I sacrificed my sleep on a work night and headed down to the club.  Only a true addict would go to a nightclub alone, fill out about 10 ballots, and wait to win a trip.

I sat at the club, bored because the draw didn’t take place til midnight.  Ironically I ran into the promoters of the first trip I won and wouldn’t you know it, they were giving away this trip too.  They made some random comment to me, “wouldn’t it be crazy if you won again? How fun would it be to bring you back to Jamaica!”

Well about 45 minutes later that comment took on a whole new meaning.  When it came time for them to go on the stage and make the draw, they announced the name…Ashley Finster!  My name is Kristi. My heart sunk, but only for the 5 minutes they waited for Ashley to grace us with her presence.  She was a no-show and the crowd was yelling for a re-draw.  They drew again.  Guess whose name was pulled??? Yea…Ashley Finster.  She must have filled out 10 ballots too.

The crowd wasn’t so lenient the second time around; we already knew Ashley wasn’t there so we all started yelling right away.  They pulled the third name and the look on their faces gave it away before they even said anything. They both started laughing and I KNEW IT!!!  The drink in my hand went flying and so did I, right up to the stage!

Yes folks, I won two trips to Jamaica within 3 years.  Even I thought it was unbelievable.  And off I went 2 weeks later, for my fourth trip to Jamaica.  And I’ve been back 4 more times since then.  A true addict at heart.

FOOTNOTE: Ashley Finster, if you ever stumble across my blog?..THANK YOU!!!!!!!


  • Eco says:

    I could use a free trip! Airfare and lodging kills me….

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  • Jamaica says:

    LOL smart ass!!

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  • Lisa says:

    I’m jealous! You must have been meant for Jamaica. It’s a gorgeous, friendly place, and I’d go back in a nano-second if I could just win the airfare…

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  • Jamaica says:

    Hey Lisa….yea I guess it was meant to be. I still don’t know anyone personally, who’s won two trips to the same place, so close together.

    I’m truly thankful.

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  • Ashley says:

    Sigh thank you other Ashley, because indirectly you not claiming your prize eventually brought about my first trip, and then life long devotion to my new homeland of Jamaica!!:D

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  • candice says:

    I am interested in this, please tell me how i can play

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  • Kristi says:

    LOL Candice read the blog post. It’s not a contest.

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