The Portuguese began their colonial expansion early in the fifteenth century: by 1417 they had arrived in Africa. They settled islands and coastal areas in Upper Guinea in Africa by 1462, islands in the Gulf of Guinea by 1500, reached India by 1510, Malaysia by 1516, Indonesia by the 1520s, and Macau by 1555. As colonization progressed, the Portuguese introduced one or more varieties of their language in their settlements and trading posts, and over time these varieties of Portuguese have evolved lexically and structurally. Spoken varieties of Portuguese in Brazil, Angola, Mozambique, and East Timor have developed different patterns that are often consistent with patterns found in naturalistic second language acquisition. They also display unmistakable evidence of substrate influence. In addition, many highly restructured varieties, the Portuguese-based creoles, developed throughout Portugal’s colonial empire, some of which are still spoken today in Africa and Asia. Apart from the substrate influence apparent in the creoles, they have also developed many features unique to them as independent linguistic systems. In this contribution, the expansion of Portugal’s colonial empire and the evolution of all these Portuguese varieties will be presented and discussed.