How to Choose a Caribbean Destination

So you’ve saved the money and you’ve spent countless hours (literally, countless) daydreaming about your vacation down south: the sun, the sand, and the palm trees. And now … it’s time to book.  But how do you choose between a slew of seemingly perfect tropical vacation destinations?

It’s simple: consider what matters most to you and what matters least.

But if this is your first tropical getaway, maybe you don’t know what matters most to you. I had no clue, either. But from my experience, there are major things to consider when trying to narrow down the choices. Read on.



For most of us, this is the biggest factor of all. Sit down and really think about your budget before you do any research at all. Then research destinations and determine which ones you can afford and which ones you can scratch off your list.


Look at destinations that offer cuisine that you’re comfortable with. Maybe you’re adventurous and know your digestive system can handle the unfamiliar, but maybe you need food you find at restaurants in your hometown. Research the cuisine at each destination you’re considering. Read TripAdvisor reviews from people who have visited and pay attention to what they say about food standards and options. Be sure to check out my post on 6 Tips for Using TripAdvisor Effectively.


Okay, you’re going to a tropical paradise and you know with 100% certainty that it will surely beat the climate back home, no matter which time of year you’re going. True! But, not all are equally balmy.

The Bahamas, for instance, is much cooler in winter than many other Caribbean destinations.

It may sound silly when you consider that by “cooler” they mean that some days it dips to 20C (about 70F) at a time when it’s -30C at home, but here’s what happens not long after we land in our paradise: our bodies quickly become acclimatized to the tropical temperatures, so very quickly we detest a 20C day when the day before it may have been 30C.


If you don’t feel comfortable speaking to people who barely speak English and can’t understand you, then you can omit Spanish speaking countries such as Mexico, Cuba, and the Dominican Republic, and choose English speaking ones such as Jamaica, Saint Lucia, The Bahamas, etc.

Flight Schedules

Research destinations that you can easily fly into and out of, if that’s what you’re looking for. Research flights that depart from your local airport. Some airlines will offer direct flights to popular tropical destinations (usually to Mexico, Cuba, and the Dominican) out of smaller airports during the winter months if there’s enough demand.

If you love the idea of driving only a few minutes to a local airport, hopping on a plane, and getting to your sunny destination within a few hours, consider choosing those locations as your destination. Otherwise you may have to drive several hours to a busier international airport to catch a flight. This obviously adds more time and effort on your part, but it often adds more money to the trip because an early morning flight will require an overnight stay at a hotel. Larger airports may also come with a heftier parking fee.


Of course crime is everywhere and you have to take precautions no matter where you are, whether it’s in the Caribbean or in your hometown, but do your diligence and research the destinations you’re considering. If you hear crime is an issue, find out if tourists are often targets or if it’s typically confined to non-tourist towns among the locals. The answer may play a major role in your decision-making process.


If you’re going there to be a complete beach bum, definitely research the types of beaches each destination has. Do you like long walks on the beach? Do you like rough water or calm water? Do you like a small, quiet beach or do you like crowded ones with lots of action? Consider what you like in a beach, or if a beach matters at all, and you will find that every destination differs in this regard.


If you’re adventurous and know you’ll want to explore, definitely research what your potential destinations have to offer in terms of excursions. Some islands may offer a plethora of the wildest excursions and tours that you can imagine, while others may offer more laid-back excursions like shopping tours and sightseeing.


These are a few of the major points to consider when researching the destination for your next tropical getaway. The important thing is to brainstorm. Discuss and research. And if necessary, do it again…and again. You’ll be less likely to regret your decision and more likely to have the time of your life (but be warned, these trips are addictive!).


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Your Friend,
Jody, The Tropical Tourist

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