Updated March 21, 2018
Plan a Caribbean trip and you'll hear lots of confusing terms thrown around, referring to different groupings of the islands on your itinerary. Two common island groups you might encounter are the Windward and Leeward Islands, as they contain many popular cruise ship port stops.
Both the Windward Islands and the Leeward Islands are island chains that are part of the Lesser Antilles (together with the Leeward Antilles islands of Aruba, Curacao, Bonaire, Tortuga and Isla Margarita). Though both archipelagos are located east and south of Puerto Rico, where the Caribbean Sea and Atlantic Ocean meet, the Leeward Islands are the more northerly in the group, and the Windward Islands are located farther south.
The Windward Islands comprise Barbados, Grenada, the Grenadines, Martinique, St. Lucia, St. Vincent, Tobago and Trinidad, which are among the larger of the Lesser Antilles islands. They are referred to as the Windward Islands due to their location on the path of Northeastern trade winds.
The Leeward Islands are composed of the many smaller islands that make up the Lesser Antilles, including Anguilla, Antigua, Barbuda, Guadeloupe, Montserrat, Nevis, Redonda, Saba, St. Barts, Saint Kitts, Saint Martin, Sint Eustatius, the British Virgin Islands and the U.S. Virgin Islands. They are referred to as the Leeward Islands due to their location away from the trade winds.
All of these islands are most typically featured on Eastern and Southern Caribbean cruise itineraries, particularly with luxury and small-ship cruise lines. However, port stops in Barbados, St. Lucia, Antigua, Barbuda, St. Kitts and the Virgin Islands are not uncommon on Eastern Caribbean cruises with more mainstream cruise lines.