Islands in the Caribbean Sea

According to multiple sources o the internet, there are “at least 28 island nations and more than 7,000 individual islands” in the Caribbean. How then, would you choose which island or islands to visit?

Largest Islands

Cuba is the largest island in the Caribbean. Until recently, American citizens were not legally allowed to visit Cuba.  Restrictions were lifted somewhat in 2014 -some were put back in place in 2017.

Which Cruise Line will You Choose?

Although it is possible to visit Cuba on your own, it is difficult; the easiest way for Americans to visit Cuba is on a cruise ship. Royal Caribbean, Norwegian, and Carnival have inexpensive cruises that stop for a day or two in Havana, Cuba’s largest and capital city.  Other cruise lines also visit Cienfuegos and Santiago de Cuba, but these cruises are usually more expensive.

The second largest island is shared by the countries of Haiti and Dominican Republic. Royal Caribbean, Norwegian, Celebrity and Carnival cruise lines all cruise to Dominican Republic. It is also safe to travel there on your own.

In recent months, violent protests have erupted in Haiti. If you want to travel there on your own, precautions must be taken. It might be best to travel with an organization that is familiar with the country. Cruises do not travel here, although Royal Caribbean and Celebrity stop in Labadee, a Haitian island leased by Royal Caribbean.

Jamaica is the third largest island in the Caribbean. Montego Bay and Ocho Rios are the cruise ports where nearly all lines stop. Jamaica is a popular honeymoon destination partially due to the number of all-inclusive resorts.

Climbing Dunn’s River Falls, Jamaica

Traveling outside the resorts on your own is not recommended. There have even been reports of attacks within the resort area, so caution is advised. Jamaica is a beautiful country, though, and worth visiting.  Dunn’s River Falls is amazing – check it out.

Puerto Rico, a territory of the United States, is the fourth largest island in the Caribbean. The capital and largest city is San Juan – often used as a starting point for Eastern or Southern Caribbean cruises. (Southwest Airlines started flying to San Juan in 2013 so reasonably priced flights may be available).

San Juan is an interesting city on its own. Visitors love Old San Juan, located on the northwest islet of the city – this historic district is very interesting. Other popular attractions include Ocean Park, Isla Verde and Condado.

Stingray Up Close

Although not a large country, the Cayman Islands (Grand Cayman, Cayman Brac, and Little Cayman) are located in the same area of the Caribbean as these larger islands. Cruises that visit Jamaica often stop at Grand Cayman as well.  Tourism is important to the Cayman Islands. The most popular spots and activities are the Seven Mile Beach, snorkeling and scuba diving (two shipwrecks are popular spots), Stingray City, and the Cayman Turtle Center.

The Bahamas and Turks and Caicos

The Bahamas is an independent British commonwealth that consists of over 700 islands, cays, and islets. It is the closest of the Caribbean islands to the United States. The islands’ proximity to the US, the weather, and natural beauty make the Bahamas a popular vacation spot. Over half of the gross national product of the Bahamas is earned through tourism.

Every cruise line offers one or more itineraries that stop at the Bahamas. The Bahamas is popular for a three day cruise. These cruises leave from Miami or Ft. Lauderdale, stop at two Bahamian ports and then return to port of embarkation. Stops may include the cities of Freeport or Nassau. More often, though, one stop will be the cruise line’s leased island or cay. These private ports have been developed by the cruise line with a resort-like feel.

Turks and Caicos, a British Overseas Territory, includes over 300 islands. It is located south of the Bahamas, although because it shares the same archipelago as the Bahamas, it is often considered part of the group. Tourism is a large part of the economy in Turks and Caicos, although financial services are also strong.

Cruise ships bring hundreds of thousands of tourists to the islands each year. Visiting the Bahamas or Turks and Caicos without a cruise ship is also popular. The larger islands are accessible by air. Resorts and luxury hotels line the beaches in popular areas.

Eastern Caribbean

East of Puerto Rico is another group of small islands known as the British Virgin Islands. This group of about 60 islands is a British Overseas Territory.  Tourism and financial services are the largest industries in the territory. Tortola, is the largest island, followed by Virgin Gorda, Anegada, and Jost Van Dyke.

Just south of the British Virgin Islands are the United States Virgin Islands, a territory of the US. The largest islands are Saint Croix, Saint John, and Saint Thomas.

Tourism and related services are the main source of income for the islands. While Saint Croix and Saint John are visited by some cruise lines, the popular Saint Thomas is visited by nearly all lines. The British Virgin Islands and US Virgin Islands are both safe to visit on your own. To travel between the two countries visitors must check in and out with a passport.

Anguilla, St. Maarten/Saint Martin, St. Kitts and Nevis, Antigua and Barbuda, and Montserrat are smaller islands located east and south of the Virgin Islands. All are British territories or in some way connected with the United Kingdom, except St. Maarten/Saint Martin which is half Dutch and half French. While all Islands are visited by some cruise lines, the most popular lines only visit St. Johns, Antigua; Philipsburg, St. Maarten; and Basseterre, St. Kitts.

Southern Caribbean

Several islands make up what is often called the southern Caribbean. Guadeloupe is a small group of islands which is a region of France. It is visited by several European cruise lines. Tourism is important to the island country, although most tourists come from France or other European countries.

The island of Dominica is one of the few independent countries in the Caribbean. Although its primary industry is agriculture (mostly banana production), tourism is increasing. Dominica is a volcanic country, so there aren’t many beaches. The island is, however, popular for scuba diving.

Martinique is a French region like Guadeloupe. Although agriculture is an important industry, it has been surpassed by tourism. The island is visited by higher-end cruise lines – some European.

St Lucia is a small (238 Square miles) independent island country. The island has both volcanoes and beautiful sandy beaches, making it popular with tourists. Most of the visitors come via cruise ship. The popular lines all stop at St. Lucia.

St. Vincent and the Grenadines is an independent sovereign state. It consists of one larger, though very small, island and a string of 32 even smaller islands. Agriculture is the primary source of income, however, tourism is growing – especially since the filming of the Pirates of the Caribbean movies on the island. The higher-end cruise lines visit this island.

The island of Barbados is directly east of St Vincent. Because it is so far east it is often referred to as an Atlantic Island rather than a Caribbean one.  Varied industries play a part in the economy of the island. Tourism has been developed and draws visitors from the Europe and North America. Several cruise lines visit the small country.

Grenada is an independent country located near the southern end of the chain of islands. The country includes the island of Grenada plus six smaller islands. The country struggles with a large financial deficit. It has focused on tourism to combat the problem. A newer cruise dock welcomes ships from all the popular cruise lines.

Trinidad and Tobago is the southern-most country in the Caribbean, made up of a pair of islands. This country is the wealthiest in the Caribbean. Tourism does not play a large part in the economy, although a few of the higher-end ships stop at each island.

Islands of the Caribbean
Looking Out to the Caribbean Sea

I realize this is a long list with a lot of facts and not as many experiences and pictures. Of all the islands listed, I have visited only two – Grand Cayman and Jamaica.  There are a lot more on my bucket list.

I’ll be crossing another island off my list in a couple months when my daughter and I visit the Bahamas. Last week I asked, “Where should we go?” – a cruise to the Bahamas won out.

What islands in the Caribbean have you been to?  Which is your favorite?


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