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Portugal credits its founding to Guimaraes, and the city accepts the responsibility with both civic pride and a certain amount of pragmatic tourism marketing. Afonso Henriques, born here around 1109, defeated the Moors at the Battle of Ourique in 1139 and declared himself the first king of Portugal. His birthplace, the Castle of Guimaraes, sits on a hill north of the old town on walls that date from the 10th century, one of the best-preserved medieval fortifications in Portugal. Nearby, the Palace of the Dukes of Braganza, built in the early 15th century and later restored, represents a style influenced by the Gothic manor houses of England and Burgundy in a way that is unusual for Iberian architecture.

The old town, inscribed as a UNESCO World Heritage Site in 2001, is one of the most intact medieval urban cores in Portugal.

The Largo da Oliveira, a cobbled square with an outdoor shrine and arcade arcades, and the adjacent Rua de Santa Maria, lined with granite houses from the 15th to 18th centuries, give a sense of a city that evolved slowly rather than being rebuilt in any single era. The Sao Francisco Convent and the collegiate church of Nossa Senhora da Oliveira frame the square with buildings whose oldest elements go back to the 12th century.