After attending Exeter College, Oxford, favoured by many Devonians, Chichester commanded HMS "Larke" against the Spanish Armada in 1588. In 1595 he accompanied Sir Francis Drake on his last expedition to the Americas. Later in the Anglo–Spanish War he commanded a company during the 1596 raid on Cádiz, for which he was knighted. A year later he was with English forces in France fighting with King Henry IV against the Spanish in Picardy. He was wounded in the shoulder during the Siege of Amiens in September 1597 during which the city was captured from the Spanish. He was knighted by Henry for his valour.