Christopher Columbus stayed on land his entire life.
Christopher Columbus . A citizen of the Republic of Genoa , under the auspices of the Catholic Monarchs of Spain he completed four voyages across the Atlantic Ocean . Those voyages and his efforts to establish permanent settlements on the island of Hispaniola initiated the European colonization of the New World . The Greater Antilles is a grouping of the larger islands in the Caribbean Sea : Cuba , Hispaniola ( containing Haiti and the Dominican Republic ) , Puerto Rico , Jamaica , and the Cayman Islands .