The Leeward and Windward islands are situated in the Caribbean Sea in a line of fragmented land masses called the Lesser Antilles. Many of the Caribbean islands are volcanic and a few are flat coral structures. The whole Caribbean Sea / West Indies region encompasses some 5,000 plus island land masses, reefs and cays. This section of the guide concentrates exclusively on travel in the Lesser Antilles region of the Caribbean from the British Virgin Island group in the north to Trinidad in the south.

The Caribbean Leeward Islands are so named due to the prevailing winds blowing north and they consist of Anguilla, Antigua and Barbuda, the British and United States Virgin Islands, the Dominican Republic, Guadeloupe, Montserrat, Saint Kitts and Nevis, Saba, Saint Martin and Saint Barts.

The Caribbean Windward Islands are so named due to being on the windier and wetter side of the Lesser Antilles and consist of Martinique, Saint Lucia, Barbados, Saint Vincent and the Grenadines, Grenada Trinidad and Tobago. Together all the islands make up the group of Caribbean islands known as the Lesser Antilles.