Planning Your First Vacation to the Caribbean

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You’ve heard of the horrifying stories, thieves, power outages, generator engines requiring repair during power outages, the hot climate, etc. These stories sound very un-inviting if you’re planning a holiday vacation. But you’re undeterred and are taking on the Caribbean for a long-deserved R&R—from Trinidad and Tobago to Martinique to the Dominican Republic.

This is going to be your first time to visit the region. What kind of preparation do you need to do for this trip? Before you start booking your flights and buying those flowery polo shirts, consider the following things:

About the Caribbean

The easiest way to understand the Caribbean is via its geo-political definition. Geographically, it consists of countries of the Americas surrounding the Caribbean Sea. On the eastern side are island countries that include, among others, Granada, St. Vincent, and pop-star Rihanna’s country, Barbados. Up north are US territories of the Virgin Islands and Puerto Rico, and countries like the Dominican Republic, Haiti, and Jamaica. On the west and the south are states of Central and South America.

Politically, it is organized into social-economic organizations like the Caribbean Community (CARICOM) and the Association of Caribbean States.

Planning Your Trip

There are, of course, those fabulous beaches. But the Caribbean is also comprised of countries with flat terrain like Aruba, Curaçao, Bonaire, and the Cayman Islands. Others are with high, rugged mountains like Saint Martin, Cuba, Puerto Rico, and Jamaica. They are all beautiful places, so you need to get your priorities straight. Here are a few things to consider when planning your vacation.

  1. Which islands? Look at the map and then look at your wallet. You need to make a wise decision as to which countries or islands you’re going to visit. Getting to some islands is cheaper than getting to others via airplane. So scout for reasonable ticket prices. A ticket that takes you to an international airport hub like Kingston might be cheaper than to islands with fewer flights.
  2. Timing. You do not want to be part of the welcome party to a Maria or an Irma. Hurricane season usually occurs during the offseason for travelers. Off-season means prices are lower, from hotels to airfares. However, travel experts have determined that the cheapest day to travel is on a Tuesday, which can save you, on average, up to $25 on your flight, and on a Wednesday, which will shave some $37 on your cost. If you’ve saved enough, it’s less risky, weather-wise, to travel during peak season. The peak season for traveling is between January to April.
  3. How much are the eggs? To get a sense of the cost of living in a country, seasoned travelers try to find out the price of eggs. The point is that you need to do your research on the cost of living in each country that you’re going to visit and factor this into your budget.
  4. Villa or Hotel Resort? Your accommodation should match your travel preferences. Are you doing a honeymoon-type vacation with your wife? Or are you going solo and prefer the non-airconditioned cabanas with a hammock? The selection you make will also impact your budget.

It’s a vacation with the sea, the beaches, the mountains, and culinary delights. Don’t let an inadequately planned vacation spoils them. These four items should get you started.

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