The Caribbean is considered to be a hot spot for travelers all around the world with many different nations, islands and generally remarkable holiday destinations to explore. Sometimes we need to unwind, relax and dive headfirst into a week or so of relaxation - and that's the sort of luxury provided in the Caribbean.

However, it's not quite as simple as that. Instead of just going for it and booking a spontaneous holiday at some point throughout the year, there needs to be some kind of thought process which goes into it.


That's because every major spot in the Caribbean is a little bit difficult or awkward to visit at certain times of the year. The reasoning behind each of the five we're going to list varies, but they need to be taken into consideration before you wind up on the holiday from hell.

This isn't intended as a piece that'll discourage you from visiting - but instead, one that'll open your eyes to the reality of travel and why it's so easy to get caught off guard from time to time.

Aruba - JANUARY TO MARCH (Soaring Prices)

The image above alone could win a lot of people over when it comes to deciding whether or not Aruba is the right place for them. It's the kind of tropical paradise that we'd all love to jet off to at the drop of a dime, mainly because it's just so secluded. Alas, with every shining light comes the realization that all is not as it seems.

To put it as bluntly as possible Aruba is an incredibly expensive destination and while that may not be a turn off for most who are planning on going, it turns out that January to March is one of the worst times to go. While the weather may be pleasant the room prices go through the roof as people search for the ultimate winter break.

The Bahamas - JUNE TO NOVEMBER (Hurricane Season)

Even if you only wanted to go over to the Bahamas in order to enjoy a nice Bahama Mama, we would completely understand. It's a wonderful destination full of wonderful people and whether you want to head to a local town, try the local cuisine or just lie on the beach and top up your tan, this is the place for you.

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Unfortunately, a decent portion of the year can be viewed as 'out of bounds' for a lot of people - and that's because of hurricane season. Typically, from June 1 to November 30, there's an incredibly high risk of hurricanes passing through the island. While the same is true of the United States, the Bahamas isn't quite as well equipped to deal with the chaos.

Puerto Rico - LATE AT NIGHT (Unsafe Neighborhoods)

The spirit and heart that can be found in Puerto Rico go above and beyond what most folks have experienced on a standard 'hot holiday' or European getaway. The cities are vibrant, the nature is breathtaking and the culture is there for all to see. Hell, San Juan alone has all of that and so much more.

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Alas, one of the primary issues following PR around like a bad smell is the crime. It's particularly bad late at night so if you happen to be on your own or in a small group, avoid and any all situations or locations that might seem shady. That includes La Perla and Puerta de Tierra as a broad view, but in reality, it spreads much further than that.

Cuba - AUGUST TO OCTOBER (Wet Season)

Cuba is as gritty as it is gorgeous with cultural spots and famous landmarks as far as the eye can see. From Viñales Valley to Old Havana and beyond you aren't going to struggle to find spots that are 'Insta-worthy', with Cuba being a hub for learning what the Caribbean is all about.

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One of the primary issues with a big holiday over there tends to be the wet season. This lasts from around June onwards but you can sort of get away with it until around August, and from then until October, it becomes less of a holiday and more of an experiment in which you see how long you can survive.

Jamaica - MAY (Rain & Crime)

From a stereotypical and historical point of view, it's easy to label Jamaica as the unofficial capital of the Caribbean, even though Santo Domingo tends to take on that reputation. The music is phenomenal, the food is great, the cultural significance of the nation is evident to all and it's just such an unbelievably colorful place.

Just try and make sure you avoid going around May time unless you want to experience the full force of the hardest and most ruthless rainfall you've ever seen.

You're also six months away from peak season around November or December, too, meaning that you won't be amongst many other tourists, and in a nation with such concerning crime rates, that's always an issue.

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