Destination, Travel

The Only Guide You Need to Narrow the Search For a Caribbean Vacation

planning a caribbean vacation

It’s time to plan a vacation, and you’ve got your eye on the Caribbean. But wait, which island? With hundreds of technical isles strewn throughout the Caribbean, trying to decide which one to visit is a true vacation conundrum. Not to worry, no need to sift through hundreds, fewer than 50 islands are actually inhabited and available to visit.

Planning a Caribbean Vacation

Still, the options are plentiful. There are a variety of ways to go about this, and we are excited to help! From topical geography to cultural layers, each island offers a different blend of features, use this guide to help discern which features are essential for your vacation.

Discover Endless Fun & Relaxation in Curacao >>

Culture Vs. Nature

Every single island has plenty of nature, but on some islands, the emphasis is raw nature whereas on others it’s a rich cultural heritage. Then, of course, certain islands have a healthy mix of both. We recommend considering whether you prefer plenty of culture or the uninterrupted views and sounds of nature.

Carnival Curaçao
Image: Lindomar Henrietta, Evento | Show | Otro (ESO)

YOU MAY ENJOY: Carnival Curaçao -The Best Carnival Celebration You’ve Never Heard of


From below Florida to just above South America, the Caribbean is an expansive region. Islands near Cuba have distinctly different weather patterns than those above Venezuela. The ABC islands, for example, feature more of a dry, arid desert climate with little rain. The smaller islands in the eastern Caribbean feature more tropical wet climates, with fierce rainy seasons.

Many of the Caribbean islands lie within the hurricane belt, in fact, nearly all of them do, except the entire southern portion. This is well-worth considering while planning your trip, as you don’t want to be caught in a hurricane, or have to deal with canceling your trip before leaving due to one. There is some data on which islands are at risk in which months, which you can read here. If you know you want to vacation during hurricane season (prices are usually less, fewer crowds, lots of benefits), you’re safest visiting a southern Caribbean island, such as Curacao.

Santa Barbara Beach & Golf Resort | planning a caribbean vacationSize


Are you dreaming of strolling around the entire coastline of an island in a day? Are you looking to run into few other souls for a week? Or, do you prefer raucous nightlife, charming towns, and abundant dining options? There are islands as tiny as Saba and as large as Cuba, with everything in between.


From the iconic Beach Boys song mentioning multiple islands to Richard Branson owning Necker Island, some islands are much more famous than others. Perhaps you fancy the idea of seeing the beaches of Jamaica yourself, or it could be you would prefer to visit an island none of your friends have heard of.

Proximity to Other Islands

Are you interested in spending a few days on one island and then hopping over to a neighboring one? Certain islands are extremely remote with no other land in sight, i.e., Bermuda, while other are happily nestled among many others. Hop around the ABC islands or the Virgin Islands.  

Santa Barbara Beach & Golf Resort | planning a caribbean vacation

Water Activities

Are you extremely fond of scuba diving? Is lounging on a soft white sand beach your idea of the best day ever? Some islands are more well-known for their underwater worlds whereas others offer the world’s best beaches, for example.

Land Activities

Ahh, something many people don’t consider. If you’re traveling in a group comprised of individuals with varying tastes and ideas of fun, you need an island with options. Not every Caribbean island is large enough to offer equal parts land and sea adventures. The larger islands will have more variety in this department. One island even has an ostrich farm.

Santa Barbara Beach & Golf Resort | planning a caribbean vacation


Caribbean cuisine is varied, but it’s safe to say seafood, rice, and BBQ are major players everywhere. Mostly we’ve added this to list so you can consider how many options you want to have. Small remote islands won’t have an abundance of dining establishments. Larger islands with bigger populations and a more layered cultural history will have varied cuisine with plenty of places to eat.

UNESCO World Heritage Sites

Another way to narrow down your options is to consider how much culture you’d like to experience. Any island with people will have a certain degree or culture, or the lack of culture IS the culture. Only a few islands feature enough culture to merit museums and UNESCO World Heritage Sites.

As you make your way through this list of considerations, we suggest taking notes on what you decidedly DO, and DON’T want in your Caribbean island! Then you can take your list and head to Google to figure out which island has your desired range of features.

Or, you can simply take our word that Curacao is one of the most well-rounded islands in all of the Caribbean, and start planning your trip!

Seriously, Curacao is:

  • Of medium size
  • Is a constituent country of the Kingdom of the Netherlands (more culture)
  • Features equal part land and sea adventures
  • Has had an intense history of different European nations ruling it
  • Features incredible scuba diving and underwater excursions
  • Is beneath the hurricane belt
  • Has neighboring islands
  • Features UNESCO World Heritage Sites
  • Has an incredible cuisine scene
  • If off the beaten-tourist-track
  • Isn’t too remote, still has Wifi and other modern amenities

We could go on, but suffice it to say Curacao is a solid option for your Caribbean vacation. If we’ve piqued your interest, take a peek at the island’s most luxurious resort, Santa Barbara Beach & Golf Resort.

Like it? Share it...Share on FacebookTweet about this on TwitterShare on LinkedInPin on PinterestShare on Google+Share on StumbleUponShare on TumblrEmail this to someone

You might also like

Leave a Reply

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