Strickland was born in Valletta, the son of naval officer Commander Walter Strickland, from the ancient English Strickland family of Sizergh, and Maria Aloysia Bonici-Mompalao, the niece and heiress of Sir Nicholas Sceberras Bologna, fifth Count della Catena in Malta, whom Gerald succeeded in 1875. He was educated at St Mary's College, Oscott, and Trinity College, Cambridge (BA, LLB). Upon graduating, he was admitted to Inner Temple in 1887 entitled to practice as a Barrister-at-Law. He gained the rank of Major in the service of the Royal Malta Militia.