How To Choose the Right Caribbean Island For Your Vacation

September 23, 2022

Image source

There are about 700 Caribbean islands split into about 13 different countries, meaning that there are about six different languages spoken across the islands. Every island has a thousand different places to visit. Hence, a unique experience awaits you on each island.

So, if you’ve made up your mind to visit the Caribbean islands, it’s a good idea to thoroughly plan your trip ahead of time. There’s a lot you need to decide to determine which of the islands will best suit your needs. We’ll be guiding you about that in this post.

But there’s also a lot to plan for, once you’ve decided on the island you wish to visit. We’ll share that bit at the very end.

Let’s get started!

How to choose the right Caribbean Island?

You must’ve seen pretty pictures of the Caribbean Island on Instagram, we bet. Perhaps, that’s what brought you here.

We ask you to visualize the dispersion of Caribbean islands on this map. Now that you know what you’re dealing with, let’s consider the factors that can help you choose the right island amongst these.

Intent of Vacation

First, determine what’s the intent of your vacation. Are you going to spend some quality time with your partner? Is this a honeymoon? Are you going to travel solo? Or are you going on a vacation with your family?

Depending on your answer, choose a suitable island. You’ll know which island suits your needs by reading reviews of the travel bloggers or exploring activities offered in each area.

For example, if you Google the best Caribbean islands for families, you’ll see many reputable sources recommending the Bahamas, Jamaica, Anguilla, and Puerto Rico. But if you Google the best Caribbean islands for a honeymoon, you’ll see these sources recommending St.Lucia, the British Virgin Islands, Barbados, etc.

Generally, here’s a list that can help you navigate your way wisely:

Intent Suitable Island
Couple GetawaysPuerto Rico
Family VacationSt. Maarten
Solo TripBonaire
Water sportsThe Cayman Islands 
Relaxation Curacao’s 
Visit many islandsBahamas

Number of People

Next to intent, we recommend considering the number of people accompanying you. If you’ve got a family or a group of friends, you might want to opt for islands that offer resorts with more rooms. Or perhaps, activities for all age groups. Similarly, you might want to visit an island that offers food and transportation at a lower cost. In this case, the Dominican Republic and Jamaica are excellent options.


As mentioned earlier, the number of people accompanying you will significantly influence your choice of island. And that’s particularly true from a monetary point of view.

So, when you plan your trip to the Caribbean Island, determine the amount you’ll be spending on this vacation. If you’ve got a lavish budget, you can consider expensive Caribbean islands, such as:

  • Musha Cay in the Bahamas
  • Moskito Island on British Virgin Island
  • Cayo Espanto in Belize
  • Nevis
  • Saint Barthelemy

But if you’re on a tight budget, you can enjoy your time at the following Caribbean islands:

  • Martinique
  • Trinidad & Tobago
  • Grenada
  • U.S. Virgin Islands

Note that the best cheap Caribbean islands may be cheap for a certain travel blogger, but they may not be cheap for you. The same applies to expensive ones.

So, you need to set up your budget, explore each recommended island in your respective category, and make rough calculations of expected expenditure. Only then, you can conclude whether an island is truly expensive or affordable for you.


You can explore the dense green forests of Caribbean islands with your kids and family. You can go camping. You can learn scuba diving or enjoy sunset boat rides. The possibilities are endless.

But if you’re going with your partner, you might prefer romantic evenings on your patio instead of exploring the wildlife. If you’re traveling solo, you might want to experience the island nightlife in its complete swing instead of ordering dinner for two from a five-star hotel.

Note that not all Caribbean islands offer everything that there is to experience. Some specialize in fun, while some specialize in romance. Hence, we recommend considering the range and nature of your activities when deciding the best Caribbean Island for yourself.

Final Words

By now, we hope you have a clear lead about how to choose the right Caribbean Island for yourself and where to start with the process. Once you’re through with step one, it’s time to proceed to step two. 

Related Posts Plugin for WordPress, Blogger...

Andi Perullo de Ledesma

I am Andi Perullo de Ledesma, a Chinese Medicine Doctor and Travel Photojournalist in Charlotte, NC. I am also wife to Lucas and mother to Joaquín. Follow us as we explore life and the world one beautiful adventure at a time.

More Posts - Website - Twitter - Facebook

Leave a Reply

Your email address will not be published. Required fields are marked *