Jamaica – Country #6 In My Mission To Visit All UN Recognized Nations

In this latest series, I will be going through all the countries I’ve travelled to from my personal experience. In this article, we will be covering country #6: Jamaica. If you haven’t gotten a chance already, read this story first to find out why I’m trying to visit all 193 UN recognized countries.

Jamaica has been a country that I’ve always wanted to visit. In my head, I envisioned a friendly country where you can walk around and enjoy the tropical island paradise weather. Little did I know that this fantasy was soon to be crushed when reality sets in.

VIDEO – Country #6: Jamaica

Going to Jamaica by cruise ship

Back in 2014, I just started getting exposed to many travel tricks and travel hacking cruise ships was one of them that I was interested in trying out. And while I learned that there’s really no “travel hacking” method for cruise ships, there are ways to get significantly discounted cruises.

The single best way to get cruise deals is to book through Vacations2go.com. That’s how I found a deal to go to Jamaica on a cruise for just $270 CAD per person. Karen and myself ended up booking a 5-day Caribbean cruise going to Jamaica and the Cayman Islands.

Arriving in Ocho Rios

When we arrived in Ocho Rios, Jamaica, the first thing that happened was we got approached by tons of sales people trying to sell us stuff. From tours to trinkets, the sheer number of touts was overwhelming. We’ve never really traveled much outside of North America before. This instance was our first experience ever getting swarmed by hordes of people trying to aggressively sell us stuff.

We tried avoiding them by walking on an alternate path from the rest of the other tourists. This turned out to be a bad decision. Because now we are walking away from the tourist path. Jamaica is known to have a lot of crime and looking in hindsight, we should have stuck to the tourist spots.

It wasn’t long before a bunch of Jamaicans found us and started following us. They kept asking us to either buy something or to give them money.

Eventually, it started raining and they ran off leaving Karen and myself drenched.

Exploring Ocho Rios

Since it started raining, we got a chance to explore peacefully. The harassment from the locals briefly stopped. We got a chance to check out some local stores. Turns out we needed some Jamaican money to buy anything. So, we ended up going in a CIBC bank branch (yes, the Canadian CIBC bank is in Jamaica) and Karen withdraw some cash.

When the rain stopped, the harassment from the locals once again resumed. One guy kept bugging us to join his tour and we told him we were broke (which was true, we spent all our savings to go on this trip). He then looked at me and I never forgot what he said next: “there ain’t no such thing as a broke China MON”.

While what he said was definitely racist, I thought it was one of the funniest thing I’ve ever heard. We just laughed and we understand, it’s hard to imagine someone broke going on a cruise (even though we were actually broke).

Eating in Ocho Rios

I wanted to eat at a local restaurant but Karen was really paranoid so we ended up going to one of the more touristy restaurants to eat Jamaican food. It was definitely a rip off and we paid a lot of money. Looking back, I would never do that if I was travelling solo.

We also got some coconuts to drink on the street as we were exploring. And quite frankly, those coconuts weren’t very good at all!

Before long, it was time to board the cruise and we were happy to leave Jamaica.

Cayman Islands

Our next destination after Jamaica was the the Cayman Islands and this was the tropical paradise that we envisioned when we went to Jamaica. This was our time to play in the beach, enjoy the weather and take some pictures of the surrounding area.


Despite my poor experience in Jamaica, I don’t have anything against the country. I understand that people are struggling to make ends meet. It’s totally understandable that you can assume people who are in a cruise ship are rich. So of course your first instinct would be to find a way to extract money from them.

I spoke about this to my Jamaican co-workers and acquaintances who live in Canada and they agreed. They told me that Jamaica is indeed a rough travel destination.

The lesson here is not to over hype a country in your head and have no expectations when you travel.

Subscribe to Travel and Live Free’s email list to get the latest blog post, updates, and to follow my journey as I work towards visiting all 193 UN recognized countries in the world!

Like me at Facebook to get the latest updates on my journey around the world. Don’t forget to subscribe to my YouTube channel to watch the latest video on my travels and travel tips.

Leave a Reply