For many travelers, the word ‘Caribbean’ conjures up instant images of sandy beaches, umbrella laden cocktails and reggae music swaying palm trees in the breeze.
That quintessential Caribbean vacation is indeed the stuff that vacation dreams are made of. But if you choose to explore further, you will find a diversified mix of lands that provide a breathtaking variety of worlds to explore.
In a circular volcanic ring between the North and South American continents, live the more than 200 million people in 35 countries and territories who have a border on the Caribbean Sea.
The region was populated by Ciboneys, Tainos, Arawaks and Caribs before the small islands and territorial waters were invaded by European foreigners more than five centuries ago. The Europeans thought they had discovered a ‘new world,’ but in fact they were in a territory that had been inhabited for four or five thousand years.
However, within a few decades the newcomers would virtually eliminate the original inhabitants, as enslaved Africans and indentured Indian labor, were brought, forced and shipped to the region by European migrants, administrators, military, entrepreneurs, and gentry who turned the verdant green hills and rolling valleys into acres of sugar cane, bananas and other agricultural commodities.
Today visitors come from every corner of the globe, to every part of the region. And those expecting to find a monolithic area scattered throughout the Caribbean will be surprised.
A traveler has an extraordinary range of potential destinations where the locals speak six official languages, dozens of unofficial and local dialects, and represent electric and entrenched cultures.
Yet some island nations are so small, you wonder how they can sustain a livelihood in the competitive 21st century world. Others are so large, you know the political or cultural meaning of their name long before you arrive.
If you want to visit the Caribbean, to understand the people, cultures, food, history and traditions – where should you go?
Regional definition
For the purposes of this article, the Caribbean includes all countries and territories that have a border on the Caribbean Sea.* For countries with land and other sea borders, this article only covers their Caribbean Sea regions, not the entire country.
In general, these territories have been influenced by one another, as well as the colonialists who lived and operated on the land for centuries, and the cultures that were brought by force.
Each is unique and merits its own exploration, but to decide where you want to go, you have to begin with your own travel preferences.
Your Criteria
Trying to decide on one Caribbean country that will highlight the whole region is a non-starter. Instead focus on the factors, activities and adventures that suit your travel style.
While most people may be looking for sunshine, beaches and watersports, you can find those activities everywhere on this list. But after you have exhausted the Caribbean vacation of your friends’ photos, what do you really want to see and do?
The Big Islands
Looking for crowded urban centers with a wide variety of cultural, historical, shopping, dining and adventure options? Your choice would be the large populated islands.
The largest populations in the Caribbean are on the islands, which were the hubs of activity for the colonial powers. Today they support vibrant, original cultures that will soak you in savory food choices, and sway your body to their globally popular music.
However visiting the larger islands also presents big population problems. With the exception of Cuba, tourists must be vigilant against criminals and other perpetrators who may attempt to take advantage of foreigners. As in all big cities, the island’s densely populated centers are not recommended for anyone after dark. And visitors should pay attention to their personal belongings at all times.
But the larger islands provide a wider variety of activity, and more historical and cultural information to absorb. These are also the business centers for the region, and the home of larger companies and small businesses. If you want to balance your visit across recreation, and education, the large islands are hard to miss.
Your destinations are: Cuba, Dominican Republic, Haiti, Jamaica, Puerto Rico
The Moneyed Islands
The scattered history of the Caribbean region during the colonial era left several small, private islands to find alternative sources of revenue. Some like Anguilla chose to pursue high-end tourists and exclusive resorts, others like the Cayman Islands became global banking centers.
Today the gross domestic product per capita (by purchasing power parity) of Caribbean nations ranges from $2,000 (Haiti) to $34,000 (The Bahamas). Economic disparity in the region is a reflection of, among other issues, history, colonial decisions, development choices made by government, and the global business environment for their most important production commodities including sugar cane, coffee and bananas. The region also gets a share of global weather disasters especially hurricanes.
Given the varied economic situations, a vacation on the moneyed islands can be tranquil, and hassle free, but also expensive.
If you are looking for a more exclusive resort style getaway, manicured and prepared for people who are willing to spend money, you can find these exclusive opportunities on the moneyed islands.
Your destinations include: Anguilla, Saint Barthèlemy, British Virgin Islands, Cayman Islands
The Quiet Islands
Fewer visitors, more open spaces, harder to reach, those are the islands with none of the popularity of their larger neighbors, but an undeterred claim to being off-the-beaten track.
As the Caribbean islands form a semi-circle around the north, east and south sides of the sea, a few locations linger just outside the reach of direct flights, and cruise ships.
If you are looking for silence, and a little effort in your adventure; if your taste buds are prepared for similarity and simplicity; and you are far beyond the need to see another museum or historic plantation house; throw your blanket down here, and close your eyes.
Your destinations include: Dominica, Grenada, Turks and Caicos
Colonial Heritage
Need to feel like you’re wandering through history with Jack Sparrow, or his French or Dutch counterpart? You will find that familiar colonial feel in the preserved, and purposefully built picturesque waterfront towns that still look as they did a century ago.
The throwback colonial heritage towns are streets of busy modern shops and restaurants today, but the facades reflect the building codes of Amsterdam or Paris, and the streets offer to take you back for a stroll down memory lane.
When you want your beach and snorkel time to mix seamlessly with quaintness, the options speak to these old world favorites beating against the sea.
Your destinations include: Curacao, Martinique, Saint Martin/San Marteen
Cruise Ship Favorites
The Caribbean is the destination cruise for which cruise ships were made. Island hopping, jewelry shopping, rum tasting in every port – the islands provide perfect backdrops for the thousands who arrive by ship every year to spend a sprinkle of time in the sun.
Cruise ships of all sizes plow the Caribbean waters, but some destinations are particularly popular and full throughout the season.
For the getaways which support one-day stopovers offering a selection of passenger-favorite foods, and easy to manage excursions, cruises are a viable introduction to the region. On a cruise, a selection of islands can be seen in succession without the hassle of airports and packing. A flavor and taste of the region can be captured in manageable trips to see more isolated areas and quieter beaches.
But on a ship, you’ll only be touching down for a brief moment, and will experience none of the adventure that true immersion can bring.
Your destinations include: Bahamas, U.S. Virgin Islands
The Edge of a Continent
The colonial legacy of the South American continent belongs to Spain and Portugal, with three northern exceptions that culturally identify with the countries in the Caribbean Sea – the Guyanas.
A territory split three ways between France, England and the Netherlands is today two countries and one territory with familiar Caribbean distinct cultures.
Since visiting the Guyanas is rarely straightforward, the three countries remain off most tourists’ lists. Yet there is an opportunity to see where the Caribbean Sea’s conflicting historical nations took control of a small slice of the South American continent.
The three countries have little of the popular imagination’s developed tourism infrastructure of their more frequently visited neighbors, and present more of a challenge to the average traveler. But if you are really looking for Caribbean adventure beyond the norm, you can look no further than these often forgotten regional players.
Your destinations are: French Guiana, Guyana, Suriname
Distinct Regions in Big Countries
The island nations dominate the tourist vision of the Caribbean. But it’s dynamic soul rested on the edge of the water in the regions of major Latin American countries that front on these waters.
The great port cities of Latin American countries were built to service the Caribbean region when Spain still called the Caribbean Sea, a ‘Spanish Lake.’ The most definitive is Cartagena in Colombia, which was the premier center in the region for centuries. But Mexico’s slave trading port at Veracruz, and Venezuela’s once manic shopping area on Isla Margarita are Caribbean mixes in their cultural rhythms and shared history.
To experience how the Caribbean ended up influencing these Latino nations, and tying the national populations unequivocally to the region, your visit would encompass these regions within nations.
Your destinations are: Colombia, Mexico, Venezuela
Singular sites
Singular sites are destinations, which stand alone from country or region to become destinations of their own. The Caribbean lays claim to the defiant beauty of the Blue Hole near the world’s second largest barrier reef in Belize; the stunning ruins of the Mayan culture in Mexico’s Yucatan Peninsula; and the connection to all worlds that is the Panama Canal.
Each of these locations is it’s own tourist book, a site that is typically incorporated into a larger trip, but remains the highlight for any discerning traveler.
While the islands may support the paradisiac vision of well-earned rest, the ‘mainland’ Caribbean offers a unique selection of rare treasure that tells the story of a greater Caribbean with an ancient past, natural wonder, and vibrant future.
Your destinations include: Belize, Mexico, Panama
Beaches and Water Sports
Perhaps there is a chance to learn to dive or snorkel for the first time; sailing or kayaking on the turquoise green waters; cycling on the dry, flat islands; or lying on any one of hundreds of white sand beaches.
Even if your criteria extends to history, culture or adventure, you can still find the time to lay back, relax and soak in the sun.
Your destinations are: just about everywhere*
Considerations
Getting there
You can fly or cruise to the Caribbean at any time of the year from dozens of ports. But air travel is usually best for going directly to one island. There are no long causeways or mega bridges artificially linking any of the islands. Once you arrive, you would typically end up staying.
Staying in One Place
With the exception of hub spots for smaller islands, air travel between islands is not convenient. Few countries have sufficient economic ties between them to merit regular flights. A land vacation typically involves picking just one island.
Island Hopping
Boat travel between islands ranges from speedboats to cruise ships and everything in-between. But the public facilities to go from island-to-island by boat are typically more defined than by air, but not as logistically common as in more developed areas.
There can be ferry services between islands within the same country like Trinidad to Tobago, or even different countries such as from St. Lucia to Martinique. But the region is not generally structured for spontaneous water crossings. If you want to island hop, your best bet is a cruise, or if you can afford it, your own boat.
Security
The larger islands and countries with big cities provide the most challenging personal security issues, but travelers should be aware of their surroundings in any location, and only do business with legitimate operators discovered through independent sources or trustworthy recommendations.
Politics
The Caribbean island nations are rarely newsmakers for conflict or instability, although unrest has certainly taken place in years past. Civil strife is typically kept away from tourists, but pay attention to any developments that change the equation.
However, the larger Latin American countries have presented a security challenge due to civil unrest. Check before you go. In many cases, the problems do not affect the coastal Caribbean areas.
Accommodations
Pitch a tent on the beach or pamper yourself in a 5-star resort. The widest range of accommodations will be on the larger islands, but all prospective tourism places will likely have a property to suit your purposes.
Food
Turn on your taste buds for delicacies and spices, old world favorites, and popular international fare. And of course, a range of extra juicy and sweet tropical fruits. Caribbean food responds to the circumstances of every country, and caters to the preferences of its visitors.
Language
The official languages in the region are European – Dutch, English, French, and Spanish, and Haitian Creole and Papiamento, the Creole of the western Netherlands Antilles.
But there are dozens of local languages and dialects influenced by the original inhabitants and enslaved Africans. The populations of Asian descent also speak languages from, or based on, those of their ancestral homes.
Learning a local word for common items can be a fun way to make friends.
Currency Exchange
Local currencies are used, but with few exceptions, the region is globally integrated into the world economy, and visitors can typically use U.S. dollars and Euros, or exchange other currencies at legitimate centers or banks.
*In alphabetical order the Caribbean Sea destinations are: Anguilla, Antigua and Barbuda, Aruba, Bahamas, Barbados, Belize, Bonaire, British Virgin Islands, Cayman Islands, Colombia, Costa Rica, Cuba, Curacao, Dominica, Dominican Republic, French Guyana, Grenada, Guatemala, Guadalupe, Guyana, Haiti, Honduras, Jamaica, Martinique, Mexico, Monserrat, Nicaragua, Panama, Puerto Rico, Saba, St. Barthelemy, St. Martin/Sint Maarten, St. Kitts and Nevis, St. Lucia, St. Vincent and the Grenadines, Sint Eustatius, Suriname, Trinidad and Tobago, Turks and Caicos, U.S. Virgin Islands, Venezuela
