Caribbean Getaways

Trips are for exploring, vacations are for relaxing. See why the Caribbean is our favorite vacation destination. Find getaway tips on which islands to visit, plus where to eat, stay, and play.

With crystal clear waters, ocean views, and sandy white beaches it’s hard to beat the Caribbean when it comes to relaxing vacations. Instead of focusing on all-inclusive resorts, we recommend off-season travel to get the most out of a Caribbean getaway budget.

From rustic getaways atop cliffs overlooking turquoise waves to historic port cities, the Caribbean has something for everyone. Here are our top vacation destinations for romantic getaways plus a few things to know before booking a trip to the Caribbean.

Romantic Caribbean Island Vacation Destinations

Cartagena, Colombia

Rooftop pool view at Hotel Ananda Cartagena Columbia
Hotel Ananda Cartagena Columbia

Cartagena is a port city on Colombia’s Caribbean coast. By the sea is the walled Old Town, founded in the 16th century, with squares, cobblestone streets, and colorful colonial buildings. With a tropical climate, the city is also a popular beach destination. 

Costa Rica

Playa Samara, Guanacaste, COSTA RICA
Low tide in Playa Samara in Costa Rica

A tale of letting go. Inspired by nature and the desire to live a stress-free life. Costa Rica became a defining moment. A trip that would change my life forever.

Dominican Republic

Travel Dominican Republic Safe Playa Rincon
Playa Rincon

My goal with this post is, to be honest, fair, and helpful for anyone looking to answer the question, is the Dominican Republic safe for travel? I’m sharing the good, the bad, and to the best of my ability a little history behind the latter.

How to Properly Pronounce Caribbean

Nothing makes travelers stand out faster than pronouncing Caribbean incorrectly. Think you know exactly how to say Caribbean correctly? In this case, it’s all about emphasis. Try saying it now. Caribbean.

What syllable does the emphasis fall on for you when you say Caribbean? First CAR-ib-be-ahn, second Ca-RIB-be-ahn or third Care-ib-BEE-ahn. Since, there are different dialects at play throughout the Caribbean knowing where to place the emphasis on Caribbean can be tricky.

By default the easiest way to understand how to properly pronounce any word is to understand the root origin. The word Caribbean comes from an indigenous tribe called the Caribs which should mean the emphasis is on the first syllable. Sticking closely to the word’s origin is usually the most respectful and most locally common option. So why do most islanders say care-ib-BEE-an themselves?

Even the Oxford English Dictionary recognizes the complexity of pronouncing Caribbean correctly.

“Of all World English varieties currently addressed by the OED, delineating a ‘Caribbean English’ provides the greatest challenge. The Caribbean is defined by the OED as the region consisting of the Caribbean Sea, its islands (including Cuba, the West Indies, Puerto Rico, and others), and the surrounding coastal areas. There is vast phonetic and phonological diversity across this region, but separate models for each nation would be impractical given the small number of terms currently in the OED from some of the Caribbean nations.”

Oxford English Dictionary

So what’s a traveler to do when trying to properly pronounce Caribbean while on vacation? Since properly pronouncing Caribbean varies depending on the island and region, when in doubt take a cue from the islanders on arrival. Since Ca-RIB-be-ahn is not correct in either the Oxford or the Webster pronunciation guides, at the very least, stay away from placing too much emphasis on the second syllable alone.

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