Scott Stoll logo world traveler. A bicycle wheel and the globe symbolizes Scott's journey around the world on a bicycle.
Sunspots on a Jamaican sunset
Sunspots on a Jamaican sunset. This is one of my all-time best photographs. I took a lot of photos of sunsets in Jamaica. But this was the only sunset that captured a sunspot. I photoshopped these side-by-side so that you can see the sunspot tracking with the sun, and that it isn’t an aberration. (Also looking like some dust is a pelican flying high above the setting sun.) There is a faint cloud in front of the sun causing the banding. I believe this cloud acted as a filter to allow my camera to see the sunspot. 

The real Jamaica

Another mis-adventure 

When we began our tour of Jamaica with Oakley, an official—“Look, I have a sticker to prove it”—tour guide, we only made a few miles before he lit up a joint.

Before I go any further with this story, I should pause with a disclaimer: If you’ve read Falling Uphill, then you know I’m more of a misadventurer than an adventurer. Though I may look like a bumbling fool, I love the surprise of leaping before I look. Even more so, I love the feeling of conquering these unexpected situations. So, rather than become the tourist with a fixed agenda and little more surprises than what you see in the brochure, I opted for the “real Jamaica”. It is a strategy that has some pros and cons, as you will see. Okay, back to the story.

Jamaica Oakley the tour guide
Oakley, our Jamaican tour guide smoking a joint.

Surprised, I said, “You can smoke a joint and drive at the same time!?” 

“C’mon Scott. This is my country. You can’t criticize how I do things in my own country.”

This is actually my number one rule when traveling: Don’t criticize someone else’s country or culture.

Well, at least not to their face. I like to get a good sampling and do a triple-check before I form an opinion. And mostly, I keep my opinions to myself. 

“It was just a question,” I said. “I couldn’t smoke a joint and drive. I’m surprised you can.”

His answer sounded like poetry.

Of course, Scott.
Of course, I can.
Who do you think I am? 
I can drive and smoke a joint.
I can drive and roll a joint.
I can drive and smoke a joint and roll a joint.
C’mon Scott.
This is the real Jamaica.
I’m the real deal. 
The real plug.

The last part was his tagline, which he said at every turn, “I’m the real deal. The real plug.” He wanted to make sure we knew just how good he was, and how lucky were to have found him. This would factor into his pleas for a tip. 

On the inside, I was thinking, “I should get out of the car now.” However, this conflicted with my philosophy. Falling uphill is a metaphor for overcoming obstacles in an unexpected way. In art school, we called these happy accidents. Now, instead of waiting for accidents, I seek obstacles. I think of fear as the door to a new opportunity. So what I actually said was, “When in Jamaica, right?”, which was the beginning of a slippery slope. 

One thing that differentiates a mis/adventurer from a tourist/vacationer is wanting to experience the real country, not the veneer built to empty your wallet. I want to meet locals, learn the customs, see how they live, what they eat, what they do for work and fun, and most importantly, I want to know what motivates them. Taking that one step further, I like to experience life as the local experiences it: do what they do, eat what they eat, et cetera. And I always like to learn a little of the local language. My favorite Jamaican expression was, “Wah gwan?” meaning, “What’s up?” And the response is, “Nah gwan.” Nothing. Or, even better, “Mi deh yah.” I am here. I love that response. “Ya mon! Everything is fine because I am here!”

Jamaica bamboo river rafting Martha Brae
When I heard we could go river rafting on a handmade bamboo raft I thought it had adventure written all over it. Actually, it is more like a romantic gondola ride in Venice, Italy. Here you see the dock with romantic couples getting ready to go.

So discovering the real Jamaica was my self-imposed challenge when I arrived in Montego Bay with literally thousands of other tourists. Most of these tourists go straight to their all-inclusive, fenced-in resorts never to be seen again. Some of these resorts cost thousands of dollars per night, where people stay in rooms with glass bottoms that float over the ocean. Little did I know, I was going to succeed at seeing the real Jamaica far beyond my comfort zone, which I think is impressive considering this is around my 70th country. (I say “around” because countries are tentative agreements between people.) 

My travel partner found a hotel run by locals with most of the customers being local. When I smashed my knuckles while closing the door, I knew I was in the right place. It’s surprising how many third-world countries build doors with knobs too close to the frame. Another threat is falling coconuts. And indeed, one night a coconut smashed the roof of our hut. Had I been standing there or sleeping in a tent… It was another close call, another misadventure.

Yes, Jamaica does retain the unflattering title of a Third World/developing country. And, if you fly straight into a resort, you may never know this. The disparity between the rich and poor is mind-boggling. Yet, the Jamaican people were wonderful. I loved the laid back spread-the-love attitude. Considering their history of having had the indigenous population wiped out, slavery, both Spanish and British rule, and years of rebellion, this was a surprise. I felt that the United States could take a lesson from Jamaica in peace and love. 

Everyone I met was full of life’s wisdom. And each had a mantra that helped them govern life. I took notes on their advice.

  • You can’t leave the same way you came.
  • Water is life. More water, more life.
  • One love. One life.
  • A bird can’t fly with one wing.
  • There is no time before now.
  • Spread the love, mon.
  • This is God’s land. No one owns it. 
  • If you got everything, then you got too much. 
  • Too much money usually falls into the hands of the wrong people.
  • What’s not meant to be is not meant to be. That’s how it is. You can’t fight fate. 
  • Never give up on life.
  • I don’t blame them. They do what they gotta do to survive.
Jamaican YouTuber
Jamaican YouTuber. A homeless man trying to raise himself out of poverty.

That last mantra was from a homeless man that I met on the last tiny public beach in Montego Bay. He grew up living under the house where the dogs sleep. He fed himself by collecting and selling pint bottles. But, now, he says, the bottles aren’t worth enough to feed himself. It’s the result of tourists driving up inflation with their easy money. He also blamed the politicians for taking as much as they could before being kicked out of office. To his credit, he didn’t beg for money. All he wanted was the phone number of an American woman. “Please, mon. I don’t want to live like this anymore. You must know one single woman.” His pleas broke my heart. Meanwhile, in the background, another homeless man was trying to turn himself into a YouTube star.

Anyway, my misadventure began outside my hotel where dozens of hawkers lurked, among them Oakley, who came with a wholehearted endorsement from some fellow Americans. “He is the real deal.” And he was. We had a whirlwind of a day. Here are a few highlights:

  • The old British jail, a tiny stone house, which is now a hole-in-the-wall restaurant.
  • The local market, not the market for tourists. Where people were more shocked to see a tourist than anywhere else.
  • We floated down a mountain river on a bamboo raft, which included a foot massage and drinks. Red Stripe is the go-to drink in Jamaica.
  • Talking with some real Rastafarians.
  • Cliff divers and sunset at one of the world’s most famous bars, Rick’s Café. 
  • Hundreds of miles of villages and beaches filled with thousands of tourists.
  • And, the day wouldn’t have been complete if we hadn’t nearly run out of gas, and finding a gas station that had only enough to give us two gallons. 
Jamaican medicine woman
Jamaican medicine woman at the local market.

But the biggest, most memorable attraction of the day was Oakley himself. He smoked at least one big fat joint per hour. Another passenger, Bryan, smoked up front with him. And when they both got going, there was a curtain of smoke in front of me. It was like being in a Cheech and Chong movie. In between joints, Oakley smoked cigarettes. Soon, I was feeling dizzy. 

The day started to really turn when we stopped at the corner store. Oakley had to buy some “numbers”. He plays the lottery morning and night, spending at least $20 per day judging by the fistful of tickets. Also, on the agenda were cigarettes, chips and beer. Even Oakley, our driver, was drinking a beer, even though earlier he had said he never drinks and drives. But this was different. “It’s just a stout, Scott. What are you worrying about?” 

“What about the police?” The police, armed with shotguns, happened to be buying chips at the store, too.

“Don’t worry, mon. Twenty dollars will make all our problems go away. And we’ll have a new friend.” 

Later we would encounter a police checkpoint, and I learned that the first thing you do is roll down the windows. They say it is to let the police see what you are doing, but I think it is to let all the smoke out. Fortunately, we got waived through because we had a trunk full of weed. In my defense, I don’t think this was illegal in Jamaica, but it probably wasn’t entirely legal either. The weed came from Oakley’s farm and was one of the surprises of his tour.

After the store, barreling down the road to our next pit stop on the other side of the island, I noticed that my potato chips tasted fantastic. “Am I high? I think I might have a second-hand high,” I confessed to the other passengers, worried I might be sick. 

For lunch, we stopped at a local jerk chicken stand. When I say local, I mean no tourists. They also had a 25-gallon pot of soup atop a wood fire. Cow stomach and chicken foot soup. Again, I confessed, “This may be the best chicken barbecue in the whole world. Either that or I am high as a kite.” In retrospect, I think both were true.

Back in the car, I find myself grateful when Oakley lights up again. I was losing my buzz. Don’t take this wrong way, I’m not a stoner. I have too much of a problem with caffeine and alcohol to really branch out. I’m just saying my mind had a mind of its own at this point. And the day was far from over. I was gonna need some help. 

We hit a few more highlights that I mentioned above, including more beer to toast the sunset. Oakley had fulfilled all his duties except taking us home, which begins after buying some more numbers. 

After the tour through the backcountry, now it was a full-tilt drive down the main highway back to Montego Bay. Where during the day it was a windy road and a lot of dodging of dogs, goats and people, now, it was a frightening 120 KPH drive through the pitch black, honking and passing cars as if they were standing still. I was fully expecting to hit an animal or who-knows-what lurking in the jungles. And several times, I thought I was going to die. This is an expression that has become a cliché, but I really mean it—I thought I was going to die. 

I analyzed/rationalized my options: 

  • This is just how you do things in Jamaica. 
  • I could get out, but being left on the side of the highway seemed much worse.
  • Oakley does this every day, and he’s lived this long. We’ll probably be okay. 
  • No one wants to die. Oakley doesn’t want to die. The drivers in the other car (which were swerving out of our way) didn’t want to die. I don’t want to die.
  • Other drivers might be even worse. There is always the threat of being robbed and left on the side of the road.
Scott playing the ukelele
Scott playing the Lava song on the ukelele. I think I have some talents, but music is not one of them. But I wanted to surprise my partner with a song in Jamaica. I knew I was going to be terrible, so I set the low bar of just enjoying myself. I spent months practicing. I had to start from scratch learning notes, strumming patterns and more. I was still terrible, but I succeeded. My partner had never been so surprised in her life. And I had fun despite being terrible. PS. After seeing this pic, I went on a diet and got a haircut. LOL.

Obviously, we made it. I handed Oakley a tip to get rid of him, ran past the gauntlet of hawkers, and slide into the gated hotel. “Whew! I think we are safe.” 

After it was all over, and sharing stories with the other passengers, I realized we had a “shared traumatic experience,” so to speak, and been thinking the same thoughts. Bryan confessed, “I thought about asking him to stop. But Oakley may never actually be sober. I was afraid he would be a worse driver if he had sobered up.” 

The downside of my Falling Uphill philosophy or leaping before looking strategy is that I expose myself as a bumbling idiot. However, my misadventures are the consequence of challenging myself to face my fears. And, the reward is living more in one day than most tourists do in a week. However, close calls are fun until they are not. So, lesson learned, next time, I can mitigate my risk. I will still want an adventure, but probably it will be a misadventure. When I was a kid, my dad paid me a big compliment; at least, I thought it was a compliment. He said, “I can’t even get mad at you. It’s not that you don’t listen, you just find always find a new mistake to make.” Haha. 

Now that I think about it, I may be a bumbling idiot, but I think it is an important life skill to embrace being bad, like I embraced my adventure with Oakley and embraced playing the Ukelele.

If you enjoyed this story… 

I’d love to hear your thoughts in the comments below.

Subscribe to get new stories in your inbox. 

If you are feeling generous, even $1 helps keep me caffeinated and inspired. Or make an anonymous gift from my Amazon Wishlist.


Leave a Reply

Your email address will not be published. Required fields are marked *

More stories like this

Footprint in the sand

Subscribe to my newsletter ​

I enjoy sending short stories about my adventures. I also send updates with free worksheets, new books and inspirational ideas to help you live a more joyful and meaningful life.