The Caribbean and Beyond: A Few Points to PonderThe Caribbean and Beyond: A Few Points to PonderThe Caribbean and Beyond: A Few Points to PonderThe Caribbean and Beyond: A Few Points to Ponder

The Caribbean and Beyond: A Few Points to Ponder

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The deeper I transition into this process of living on a Caribbean island, the more complicated I’m realizing it is.

There are many tradeoffs when choosing a Caribbean lifestyle. At times, living in Jamaica makes me feel I’m navigating ship in the dark. I’ve made some mistakes that have set me back dearly but I’ve also gotten a few things right. I’m hoping that sharing them will help you avoid costly and painful errors as you make the huge decision about starting this new chapter.

Traveling someplace new is sort of like a first date.  Have you ever met someone new and suddenly believed in “love at first sight?” Maybe it was in college, at work or on a dreaded blind date.

Whatever the case, after you had fallen for this person, it seems as if they could do no wrong. They have no irritating habits, always know just what to say and as you look towards your future together, it’s all sunshine and happiness. You expect sweet bliss, right?

Then, after a while, or perhaps just after you’ve said your vows, suddenly you “realize” that he sits on a the couch and picks sock lint from between his toes while he watches TV. You wonder when she start chewing with her mouth open. Why didn’t you notice the piles of trash in the floorboard of his car when you were out on dates?  How did all of that escape you? Like they say, “love is blind.”

Being enamored with a far-flung location can cause blindness, too. I lived in Italy just out of high school. I really enjoyed the culture, the history and the food. Initially, as a flaming redhead, I suffered great embarrassment at the attention paid to me by Italian men. This slowly blossomed into reveling in the admiration. Eventually, however, it petered out to shear annoyance following several months of being hounded and even “handled” everywhere I went. As things become familiar, the glow wears off and reality sets in.

I’ve frequently been accused of wearing rose-colored glasses when it comes to Jamaica. I’ve had many people, including Jamaicans, stand me against a wall, with a finger in my chest, telling me how insane I am to want to live here.

They cite the issues of crime, poverty and corruption as critical points in their reasoning. A few have come right out and told me that I’ll never “make it” here. Straight from my “southern, redheaded woman, stubborn roots,” I’d like to say, “them’s fightin words!”  Ha ha.

It’s not that I ignore their insights or that I don’t acknowledge the reality of the facts they state. I’ve been reading Jamaican newspapers for five years now. I talk to Jamaicans virtually every day and KNOW what’s happening here.

Although I don’t totally understand how it got this way, I see the broken system and the broken people. I have no illusions that it will be miraculously “fixed,” nor do believe myself to have any brilliant solutions. I simply love this place and it’s people in a way that even I don’t understand sometimes.

Meanwhile, I see mass murders in my own country that happen not because of poverty or because someone snitched or was flashing money around in public. No, these killings happen “just because.” I find myself edgy in crowded or popular events in the USA, wondering who might be “the next shooter.” I look at our American political system and have to ask if we have the right to point the finger at ANY country and chastise them for their corruption. Seriously.

Nearly every “destination” around the world is now marketed, suggesting how fabulous life would be if you “owned” a piece of their amazing town…history…view…or some other selling point.

Go to any vacation spot and there will be realtor magazines and billboards strategically placed to lure you in. We have all taken a vacation and thought, “Man, it must be amazing to live here.” We so easily gloss over what we don’t want to see.

Whether it’s the mountains of Kentucky, the hills of Tuscany or the beaches of Jamaica, it takes time to grasp what life is like there, day-to-day. 

Obviously, there are certain realities that you must contemplate before taking the plunge into life in Jamaica, the Caribbean in general, or any foreign country, for that matter. You want to intimately know what you are getting into before you take the leap, at least as much as is possible. What seems charming at first glance, can become deeply irritating in the long-term.

It can be challenging to see below the surface very deeply. Let’s face it, realtors, restauranteurs, and the service providers that enable you to make the transition often have a vested interest in you going through with it. If not, they lose income. Even resort owners need to keep you coming back and it will be a long while before you hear the rest of the story from them. 

It only stands to reason that many of these sales pitches tend to leave out or shelter prospective customers from anything frustrating or unseemly. In other instances, the vendors are so accustomed to “the way things are,” that they simply forget to mention that the power goes off in a particular town on a regular basis or that you will only have water every other day.  

I would highly advise that you visit a place many, many, many times before you even begin to contemplate investing your energy, emotions and resources there.

It should go without saying that staying in all-inclusive resorts isn’t reality. Not with maids and servers meeting your every desire, a big smile plastered on their face. When asked about their real lives, they are going to tell you it’s all a bed of roses…because that’s what they are trained to do.

Instead, take it down a notch and vacation in some of the smaller, family run motels, guests houses, or villas. You will begin to reach into the local communities and can meet the people who live there. Observe closely to get a feel for what their daily lives look like.

Too afraid to leave the security of your resort? The country is probably not for you, unless you plan to live out your days behind locked doors, in a gated community.  If that’s the case, why bother?

While you are checking out various lodging options, don’t forget to check out multiple locales.

In Jamaica, for example, each parish has its own, distinct flavor. The famous 7 mile stretch of white sand beach in Negril, is full-on resort style life. Offering low-key, locally owned accommodations, the entire “strip” is chocked full of restaurants, shops, loud, busy nightclubs, tour groups and aggressive vendors. It’s not for everyone and yet other people couldn’t do without it.

Further east in Jamaica, life is quite low-key and slow by comparison. The weather is cooler and they get more rain so the jungles are thick with vegetation. There are mountains that rise above the sea. Even their version of Patois, the local dialect, is different. You almost feel like you’ve entered a different country out there.

By contrast, my area, on the south side of the island, is mostly open spaces and is generally drier. It’s inhabited almost entirely by local people doing local things. There are fishermen building fish pots in their yards. Farms are growing and selling fresh produce.

It’s the kind of place that is more about playing dominoes on the verandah, gathering for community functions, and hanging out with friends and family. Even in the relative peace of my spot, I’ve found things that leave me scratching my head, as you can read about here.

Things are a little more lively during the tourist season, January until April, but the sidewalks still roll up between 8 and 9. I’ve actually run into tourists on the beach here who, barely checked into their rooms, have stopped me to ask, “Where’s the nightlife? Where’s the excitement?” or “What is there to DO here?” At that point, I usually find them a driver and send them packing off to Negril.

There are pros and cons to all of life’s decisions. There is no utopia. All of life is a balancing act.

Marrying the person you only met a few months ago and moving to a foreign country, especially a developing country like Jamaica, are quite similar. There will be days that you kick yourself and other days when you smile so widely that you expect your face to crack. I speak from experience because I’ve done them both more than once. Here’s hoping your future holds a lot more grinning.

To read more about integrating into life in Jamaica, check out this post.

Feel free to drop a comment below.  If you’d like to keep up with our adventure, please take a minute to subscribe to our email list in the upper right corner.  We won’t load up your inbox or sell your info.  We will, however, keep you updated.  Blessings to you!


I'm a wife, the mother of ten children, a retired dairy goat farmer and cheesemaker, and I love to travel, write and take photos. My favorite hobby is walking the beach and searching for sand dollars.

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  • malika dakkon
    January 19, 2018 at 2:30 pm



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I have traveled all over the world and fallen in love with many places in my lifetime but none of them grabbed me as intensely as Jamaica. During my first visit, years ago, I felt as if I was coming home for the first time in my life. I look forward to sharing this journey with you as I begin the long process of making Jamaica my actual home. These are my experiences and observations. I hope you can see Jamaica through my eyes, and love her the way that I do. I am Jamaican at heart.

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