This has got to be one of the most ridiculous things I’ve done and probably this trip shouldn’t even count towards my trip totals, but nonetheless I did it and it was quite the whirlwind experience! Take two crazy Canadian chicks with birthdays in November; one with hotel connections and one with flight benefits. Put them together and you have a recipe for adventure! NOTE: Little bits of info have been altered just to save time. This post is already too long!

In November 2009 I got an offer from an all-inclusive resort in Runaway Bay, Jamaica for a couple nights free stay to write a review for them. This is the ONLY time I’ve done all-inclusive on purpose. One of my best girls, Erin who works for an airline (and just happens to have a wicked food and recipe blog) had just added me to her flight benefits so we decided it would be a good idea to take the hotel up on it’s offer. We knew it would be a risk since flying standby is never guaranteed until you’re on the plane and rolling, but it was a risk we were willing to attempt!
I remember my departure night like it was yesterday, Erin calling me as I was leaving for the airport and telling me my flight to Toronto was oversold and it doesn’t look good. But I had to go try anyway, just in case. So I got to the airport, sat at the gate and prayed. Every single last person had boarded the plane and I was alone and waiting for my name to be called on the off chance that someone never showed up for this flight. Erin was at the other end of the country (New Brunswick) waiting on my word because if I didn’t get on my flight she wouldn’t bother getting on hers. Finally the gate personnel looked at me with a grin and called my name. I literally got the LAST seat on that plane! I quickly texted Erin and told her to get on her flight!
The challenge wasn’t over yet though. Four hours later her and I met at Toronto’s Pearson airport at about 7:00am (my first flight was a red-eye), had breakfast and headed to our Montego Bay flight gate. There was also a chance that we wouldn’t get on this flight because it was pretty full and we were standby. So we sat at the gate waiting again when finally we were told that we will not be getting on. My heart sunk because the only option was to turn around and just fly home. But the agent at the gate said there is a flight leaving for Kingston around the same time and that we should run over there and get listed on their standby list! Away we went, running around the corner to a new gate FULL of Jamaicans waiting to fly home and we sit and wait again for our names to be called.
Again, we waited until almost everyone had boarded the plane. We even waited through them calling other standby passengers to board as if we were on the bottom of the list. Erin and I actually started planning our trips back home because we were so sure we wouldn’t get on this flight, when shockingly, our names were called! I’m telling you this was such a last minute change of plans that I was calling our ride from Montego Bay to pick us up in Kingston AS we were boarding the plane!
I remember this flight into Kingston as one of my best flights ever because the plane was full of returning Jamaican farm workers going home for the winter. I had a middle seat between two workers and got to know them on the way down. They were scared shitless of the flight and they prayed a lot because of it. Of course, in true Jamaican style, by the time we arrived one of them already thought I was his girlfriend and had asked for my number a hundred times. Our flight touched down and we were through immigration faster that I’ve ever experienced because in Kingston it’s the Nationals line-up that’s long and the tourist line was non-existent. We were outside the airport in about 15 minutes and Damian (our ride) was there for our 2-hour drive to Runaway Bay.


We enjoyed the countryside on the drive, stopped to buy jackfruit, filmed ourselves driving over flatbridge and through Fern Gully, etc. By the time we reached Runaway Bay it was dark and the clock was ticking on our countdown back to Canada. Eeeww that sounds horrible having just landed! We couldn’t waste a minute of our time! The first thing on the agenda was to surprise one of our Jamaican friends at a local bar on the road beside the hotel. Some of our friends knew we were coming and were all in on the surprise but one of them didn’t know so the bar thing was a set up to surprise him. It was executed flawlessly and his surprise is captured in the video below.
After the surprise Erin and I went to check into the hotel. This whole resort thing is new to me and I have no clue what to do inside these gates but I knew there was free food, liquor and entertainment so that’s where we went! I overindulged in the rum and Jamaican food buffet while we watched plenty of cultural entertainment in the main stage area at the hotel. I could dig it! However I knew I would NOT be satisfied for long inside here but the tiredness of the journey combined with free alcohol took over and we knew we needed to sleep. I wanted to be up early the next day and not waste any time of our first (and ONLY) full day in Jamaica.
We were up at the crack of dawn the next morning and since I was doing a hotel review I decided to go do hotel stuff, like check out the pool and see if I could bribe a bartender into serving me long before the bar opens. Yes, I had my first rum of the day at 9:30am, poolside….before the bar opened. Later in the morning Erin and I parted company for a while. She opted to stay on property while I went back to the road bar to link up with a bunch of Jamaican friends who weren’t allowed inside the hotel….reasons I hate hotels. I lingered at the road bar ALL day until I was starving to death and forced to go back and eat since the food was free.
That evening we celebrated birthdays for free with food, wine, cake and all the trimmings. I keep highlighting FREE because I’m not used to getting what I want without having to pay for it! What a concept! After dinner we watched some more of the hotel entertainment which was a sexual position contest….similar to musical chairs. When the music stopped all the couples had to land in some position and they would be eliminated based on lameness. It was hilarious! Erin and I then became stars while butchering Shaggy’s “It Wasn’t Me” at hotel karaoke while under the influence and then decided we were ready to party. We opted for the go-go bar across the street which was a hundred times more fun! We walked across the highway and into the bar where there were some pretty hot Jamaican females up on stage doing their thing. I’m always amazed at the dancers in go-go bars. My butt used to move that way back in the days when I would practice Jamaican dancing!
The night went on and eventually the bartender started offering me free drinks in exchange for getting up on stage and doing my own dance. I’m brave like that and I ALMOST went up there but decided at the last minute that I hadn’t drank enough so I opted out. But I did have a slammin’ good time at the bar that night and in my opinion, we left too early at 1:00am. Our dilemma was leaving the next day though, we still had to be up at a reasonable hour to eat and be ready for our airport bus at 10:30am. Wow, it was really over that fast.
My standby flights home were uneventful, I made it on both as scheduled – seated between a snoring guy and a surrogate mother. I highly do NOT recommend 48 hours in Jamaica when you have to fly for 24 hours on top of that. But would I do it again? In a heartbeat!
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