I Once Won a Free Trip to Cancun Because My Friend Had a Weak Bladder

mariachi statue

“If I win, I promise to take you!”

I made this half-joking vow to my new friend Erin as we dropped our entry forms into the box at the movie theater on the South Side of Pittsburgh.

We had only known each other for a couple of months, having met on MySpace back in 2005 when people legitimately used social media sites to make new friends, as opposed to simply reconnecting with old ones (I miss those days…)

Erin and I went for a walk around the South Side one evening, with no real plans except to chat and hang out. At one point, she had to pee, so we ducked into the movie theater. While she went to answer nature’s call, I noticed a box on the ticket counter.

“Win a trip to Cancun! Win a trip to Punta Cana!”

Whatever, I thought. I had never won anything in my life, except for a plastic mug bearing the logo of my high school back in a 7th-grade school drawing. This contest appeared to be sponsored by a local radio station and the prize was a trip for two to the tropical destination of your choice.

cancun resort

I had time to kill, so I grabbed the only writing utensil available, a dull pencil in my backpack. As I recall, I had to bite off some of the wood to get the lead to emerge so I could actually write with it.

I didn’t bother to fill out most of the form, because I didn’t want spam or junk mail coming my way. So I listed my name and phone number, but I ignored the email section and probably used a fake mailing address.

When Erin returned she filled out one too, and we agreed to take each other if one of us won. I completely forgot about the contest about two minutes after I walked out of the theater, and that was that.

Imagine my surprise a couple weeks later when I got a call from a guy at the radio station, informing me I was one of five finalists for the prize. To win, I had to compete in a scavenger hunt at the South Side Works that weekend.

I didn’t know what this scavenger hunt would entail, but assumed it would involve being given a list of items and having to run around and find the stores that sell them. So I spent the three days leading up to the contest going into every store in the mall, memorizing which items could be found in which places.

The day of the event, I sized up my four competitors. One young woman had just gotten married and was hoping to use the trip as her honeymoon. Her tearjerker story may have made her the sentimental favorite to those watching, but I was unmoved. I had a vacation to win!

It turns out that my advance studying was unnecessary. All we had to do was unscramble a list of store names, run to those stores and pick up a piece of paper from the register at each place, and run back to the starting point. As a fit young adult male, I had an unfair advantage.

I raced around the mall from store to store, and when I made it back to the start, I discovered I was the first one there. I had won! Because my friend had a weak bladder and I was a fast runner, I won a trip to Cancun!

I called Erin to give her the good news, and over the coming weeks we planned our amazing vacation. Seven nights at an all-inclusive resort just south of Cancun.

I don’t even remember the name of radio station. Sorry, guys. But thanks for sending me to Mexico!

People really do win those things.

The Week-Long All-Inclusive Stay in Cancun

cancun beach

After winning a free trip to Cancun several years ago, my friend Erin and I booked the week-long vacation for early November.

It turns out that Hurricane Wilma, a category 5 storm, ripped through the Yucatan Peninsula just a week before we were scheduled to fly there. Yikes! Several days’ worth of flights were canceled, but everything was back on schedule just in time for us to make the trip.

The best thing about this vacation in Cancun was that it was all-inclusive, meaning everything was paid for. All-inclusive vacations are really a cheap way to travel to Cancun since you don’t have to worry about unexpected expenses.

The resort restaurants and bars were open all day (and in some cases, all night), and we could go in and get unlimited meals and drinks for the entire week without paying a thing.

We spent a week bouncing around from Cancun to Tulum to Playa del Carmen. Unfortunately, we didn’t make it to the island of Cozumel, one of the best scuba diving spots in the Caribbean, but that’s on our bucket list for next time!

At the resort, we enjoyed the free fruity drinks for all!

cancun tropical drinks

Wine on tap?! I had never heard of such a thing.

wine on tap

In retrospect, I’m not sure why we didn’t just spend the whole week at the bars enjoying the free booze. Oh, wait, I remember. Because we spent it at the beaches instead.

friends beach

Because of the hurricane, the resort was sparsely crowded. It was maybe 20% full, which meant that at most of the fancier restaurants, we were the only ones there.

The waiters would come up and ask, “You want tequila?” at every meal – even breakfast!

mariachis restaurant

At one dinner, we were serenaded by a mariachi band.

And after the meals, it was back to the beach.

beach chairs

The laid-back week was the complete opposite of my current travel style, in which I cram as much as possible into a few short days.

me beach

The resort itself was spectacular.

Everyday during the vacation in Cancun, we would find a gift from housekeeping – a towel twisted into a random animal shape. On this day, it was a swan.

hotel bed

This was my first experience with a minibar. Normally, I don’t touch these, because they’re so expensive. We weren’t sure if the minibar was part of the all-inclusive package, or if we would have to pay for anything we ate.

So on the first day, we drank just one bottle of Dos Equis. When we weren’t charged, we knew we had the green light to go nuts and empty it everyday, because it would be replenished the next day at no cost.

resort minibar

I did want to incorporate some cultural experiences into this trip, but because of the hurricane and ongoing clean-up efforts, many of the tours were canceled.

We were able to sign up for a tour of Mayan ruins near Tulum. After a short hike through the forest, we arrived at the ruins.

tulum ruins

The steps on these ancient structures were very narrow, so they have installed a rope to aid visitors with their ascent.

ruins stairs

Looking back down from the top.

selfie ruins
view from top

We also visited a local Mayan community. More than 6 million Maya still live in Latin America today. Our guide was friendly with one particular family and invited us to catch a glimpse of their way of life.

maya family

Their way of life consisted of large families living together in small huts while turkeys, ducks and chickens roamed around.

maya chickens

Our guide told us that she gives the family a payment whenever she brings in tourist groups. So while it felt a little odd that their whole life was on display for all of us camera-wielding tourists, at least they were benefitting from the arrangement.

maya children

The tour company also offered a snorkeling tour in a cenote, a deep natural sinkhole teeming with wildlife.

Unfortunately, the snorkeling part of the tour was canceled, but we did get to stop by the cenote to see the turtles swimming around.

cancun mexico

We also stopped at a market that had locally-made artwork for sale. Most of us just browsed, although one lady was an experienced haggler who scored a couple of deals.

shopping mexico

Our resort was actually an hour outside Cancun, near the town of Akumal. So we didn’t get to spend time in Cancun proper, but we did get to have a somewhat urban experience when we boarded the local colectivo bus into the town of Playa del Carmen.

playa del carmen

Playa Del Carmen had an active business district. I loved the store that sold gifts and novelties, like these skeleton dolls.

skeleton dolls

We stopped for an authentic Mexican meal.

playa del carmen meal

The restaurant had a humorously mistranslated sign on the bathroom door.

bathroom sign

And then it was back to the resort for some more lying around at the beach.

beach sand

When we were tired of sitting at the beach, we moved back to the pool. The choice of where to spend our leisure time was so perplexing.

poolside resort view

It was a really tough call, and you should feel sorry that we had to make such painful, agonizing decisions.

resort pool

They even had little trams to drive us to the beach, in case we didn’t feel like walking. Talk about being spoiled!

bus shuttle

We only got really crazy with the drinks on the last night, when we went to one of the resort nightclubs and freely accepted the complimentary tequila.

I remember spending some time on the dance floor trying to communicate in Spanish with these guys who only spoke Italian. Good times.

This blurry pic from the club is one of my few memories from the evening.


The good times ended on the flight home the next morning, when we were both borderline sick. Under normal circumstances, this might have been a miserable experience, but because there were fewer than 20 people on the plane, we got to stretch out and sleep it off.

The scariest thing about the plane was the “dinner” – some sort of microwaved box of food. I’ve never had another actual meal on a plane so I don’t know if this is what they all look like.

airplane meal

Other random memories from the trip: Watching South Park on the hotel tv with Spanish words dubbed over the original voices; being amused by the sight of spider monkeys on leashes in neighborhoods; wandering through backstreets of Playa Del Carmen and having more than one local ask us if we wanted to buy pot; wondering if they had dyed the water in the ocean because it was so clear and blue and there were so few fish.

Cancun was fun, and it instilled in me a burning desire to travel that has not subsided yet!

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