Alright it’s time to be straight with me and with yourselves about your Jamaica addiction. I’m about to spill the creative ways I’ve funded my obsession for so long so you have to share yours in the comments below too! Actually when I sit down and think about it I can’t come up with anything overly ridiculous I’ve done to afford any of my sixteen trips but there are a few things in there that make me laugh.

There’s only one trip I can think of where I was completely scandalous in order to get my ticket. Back in those days a CHEAP ticket from where I live was $800.00 – no joke. One month I lied to my landlord about major car repair problems and asked if I could skip the rent and pay it back in installments. He was great and agreed and I bought my ticket to Jamaica. It sometimes paid to be a single mother because people felt more sorry for me and were willing to cut me a break sometimes but little did they know.
Several years ago I became virtually debt free and paid off my car, got rid of credit cards and all loans so life was great at a zero balance but I had no more credit cards. I didn’t mind not having them until it was time to start shopping for airline tickets which I did every few months. Lucky for me I had awesome coworkers who all collect points on their cards so every time I was at my desk and saw a fabulous seat sale I would just ask a coworker to book it! They collected their points, I paid them in cash and I was always good to go!
Another great way to get to Jamaica cheaply and I highly recommend it is have a BFF (I love you!!) who works for an airline. A couple years ago one of my girls added me to her family and friends flight benefits with the airline she works for. Before you hate me I want to point out the negatives to this plan! First of all you have to fly standby which is never guaranteed and I’ve been stuck and unable to board in different cities more than once! Unfortunately I’ve never been stuck and unable to board in Jamaica, only every other city trying to get to Jamaica. Another downside is that I collect points for this particular airline BUT if I fly standby I don’t get points for those flights. So in the long run I would probably have double the points and free flight possibilities if I’d actually bought confirmed tickets.
I think those are all the creative ways I’ve taken my sorry ass to Jamaica over the years, aside from just buying tickets and winning trips (twice). So now it’s time for you to share! Tell me below the craziest or most creative ways you’ve funded your addiction! There’s gotta be some great stories out there, I know you guys!
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