Portugal in World War II was neutral, but Salazar’s decision to stick with the oldest alliance in the world, cemented by the Treaty of Windsor (1386) between Portugal and England, which is still in force today, meant that the Anglo-Portuguese Alliance allowed Madeira to help the allies and in July 1940 around 2,000 Gibraltarian Evacuees were shipped to Madeira, this was due to the high risk of Gibraltar being attacked by either Spain or Germany. The Germans had planned an attack and codenamed itOperation Felix, which was never initiated.
The Gibraltarians are fondly remembered on the island where they were called Gibraltinos. Some Gibraltarians had married Madeirans during this time and stayed after the war was over.
On November 12, 1940 Hitler issued Führer Directive No. 18 in which there was the possibility to invade Portugal and he also said “I also request that the problem of occupying Madeira and the Azores should be considered, together with the advantages and disadvantages which this would entail for our sea and air warfare. The results of these investigations are to be submitted to me as soon as possible.
On the 28 May 1944 the first repatriation party leaves Madeira for Gibraltar and by the end of 1944 only 520 non-priority evacuees remained on the island.
More recently a monument was made in Gibraltar and shipped to Madeira where it has been erected next to a small chapel at Santa Caterina park, Funchal. The monument is a gift and symbol of ever-lasting thanks given by the people of Gibraltar to the island of Madeira and its inhabitants.