Caribbean Travel Guide

The Caribbean Sea is a sub region of North America bordered by the Cuba and the other Greater Antilles to the north, the Lesser Antilles to the east, South America, and Central America. Before Christopher Columbus sailed through on his historic voyages these islands were settled from South America northward by the Arawak, Taino, Lucayan, and Carib indigenous people. During the Age of Exploration the islands were fought over by the English, French, Spanish, Dutch, and other European nations as slaves from Africa were brought to work on the plantations (sugar being one of the biggest exports). During this time the world saw the so called “Golden Age of Piracy” and most of the celebrated pirates come from this time period in the Caribbean.

Today when one thinks of the Caribbean they think of tropical islands with crystal clear water, amazing beaches, and colorful reefs. Some of the islands are independent countries and others are still part of a European nation. The people are predominantly descendants of formal slaves and the economies tend to be lower than European standards. Each island has its own culture, but there is a “Caribbean feel” throughout the region. For this reason I am considering the Caribbean as the islands on the north and east side of the Caribbean Sea along with the Bahamas, Dutch ABCs, and Bermuda.

I had the good fortune of sailing my boat throughout the entire Bahamas and Turks and Caicos island chain for seven months in 2011. During this time I saw every island except for Inagua Island. This includes spending several days out at remote Hogsty Reef (a 3 x 5 mile atoll) halfway between Acklins Island and Inagua Island. In fact, starting in 2016 I was asked to write a month column in the South Florida edition of All At Sea about each island in the Bahamas.

Once I finished sailing through the Bahamas I started a charter business and sailing school in the US Virgin Islands and have been venturing into the British VI and Spanish VI (along with Puerto Rico) ever since. Starting in April 2017 I have been carving out time to cruise south to the different islands of the Windward and Leeward Islands of the Caribbean.

If you would like to learn more about a particular country just click on it in the map below. Of course you can also jump over to the travel video pages for the Caribbean, Bahamas, or Virgin Islands.

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