Leeward Islands Leeward Islands are not limited to Guadeloupe alone. It is a group of small islands in the northern part of the Lesser Antilles. The islands are located within the joining of Caribbean Sea and Atlantic Ocean. These islands start in Puerto Rico and goes down to Dominica. Guadeloupe’s Leeward Islands is somewhere between all that. In fact, Guadeloupe is in the south portion and is connected with the Windward Islands or the south portion of the nineteen Leeward Islands.