No Matter What You Like, There’s a Caribbean Island Perfect for You

There are thousands of individual islands dotted around the Caribbean, although this can be whittled down to dozens when you reduce them to the individual countries that they belong to. But still, there are a lot of choices when it comes to which Caribbean country is best for your vacation.

OK, so it feels a bit easy to simply say that they are all utterly charming, but it’s not as though you can make a wrong choice when choosing one place over another. It really depends on what kind of island experience you want to have, although chances are that you’ll want it to involve a fair amount of sun and surf. It’s not as though you’ll have the time and money to work your way from island to island, enjoying the distinctive culture of each.

So how do you narrow down your options when deciding which Caribbean island is perfect for you?

  1. Jamaica: Reggae and Gritty Charm


Want to get away from the idea of staying in a fancy resort? Perhaps you want to listen to some reggae and smoke something a little bit “exotic”? Jamaica certainly has the ability to offer you a luxury experience if you’re willing to pay, but this is not why the majority of people come. If you want to spend your days on a dramatic looking beach while listening to music with like-minded people before sleeping in a tent, a van, or a downtrodden hostel, then Jamaica is for you. While the place could accurately be described as being chilled out, you should be wary about being too chilled out.

There is a relatively high crime rate on the island, so the necessary precautions should be followed. Despite its relaxed reputation, Jamaica is also quite conservative in a number of ways, particularly with regards to LGBT individuals, who are sometimes viewed with suspicion. Kingston’s Norman Manley International Airport provides flights to the US, Canada, the UK, and a number of Caribbean destinations.

  1. Cayman Islands: A Caribbean Playground


A number of travel guides have pointed out that the Cayman Islands (Grand Cayman in particular) can remind you of Florida, which is not all that far away. But Florida is a whole other world, and while the Cayman Islands place an emphasis on holiday resorts, the islands have their own unique culture (without the crowds of Florida).

The placid waters around the islands when coupled with resort living make the Cayman Islands a relaxing choice, although perhaps not the best place if you also want to get out of the resorts and experience an authentic rural way of island life. You will almost certainly arrive via Owen Roberts International Airport, with flights to the US, Canada, the UK, and Cuba.

  1. Cuba: Friendly and No Longer Forbidden


Cuba requires a little more planning than some other islands, although its forbidden qualities are quickly evaporating as the country once again becomes friends with the US. Even as it opens itself up to more tourism, the island makes for an undeniably unique experience that is weighted with history. You should allocate as much time as possible to see Cuba, and even if you stick to Havana you should see as much of the surrounding towns as possible, like a Varadero and Havana tour.

Many of the stereotypes are true, and you can spend your days drinking rum on the beach with a big fat cigar in your hand (although there is so much more to the place than that!). Most arrivals in Cuba will be via Havana’s José Martí International Airport (although other airports are scheduling international flights to meet demand). There are direct flights to Canada, the UK, Russia, France, Germany, Italy, Spain, Austria, Finland, the Netherlands, Angola, China, and many Latin American countries. There are also a number of special charter flights to the US, and these flights are expected to be deregulated in the not-too-distant future.

  1. Puerto Rico: A Close Cousin


While it’s not technically a US state, Puerto Rico is in fact a sub-national administrative division of the US, which makes it a pretty darn close cousin. It’s both a self-governing nation and a US territory. It’s an arrangement that might seem weird to the rest of the world, but who are they to judge? Puerto Rico allows visitors to easily make their way between the island and the US, in a way that is much easier than when US visitors want to make their way to Cuba.

San Juan feels like a true city, with a metropolitan population of close to 2.5 million. The population quickly disperses once you leave the city, and the beaches are rather lovely, particularly when contrasted with the arid beauty of the interior of the island. Given its ties to the US, Puerto Rico can feel like a safe bet for a Caribbean holiday, although this doesn’t make it any less lovely. Most entries to Puerto Rico will be via Luis Muñoz Marín International Airport, with flights to the US, Canada, Spain, Germany, Denmark, Norway, Sweden, and many Latin American countries.

  1. Barbados: Welcome to the British Empire
Aerial view of Holetown, St. James, Barbados

Aerial view of Holetown, St. James, Barbados

OK, so Barbados is no longer part of the empire (and the empire doesn’t quite exist anymore). But it is still a Commonwealth country, meaning that Queen Elizabeth II is the head of state, much like in Canada, Australia, or New Zealand. Unlike those places, Barbados has retained somewhat of a colonial feeling, with a high population of British expats.

It’s a weird and amusing mixture of sensibilities, with the appropriately laid-back nature of the island meshing interestingly well with the more formal way of life preferred by those who are trying to recall the island nation’s colonial heritage. The largest city is Bridgetown (approximately 110,000 people) and the island is serviced by the Grantley Adams International Airport. There are direct flights to the US, Canada, the UK, Germany, and a number of Latin American destinations.

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