Allan was born in 1872, the second son of that name born to Duncan MacAskill and Effie MacLeod, cottars on 11/12 Ruisgarry (Quay). Allan became a farm servant. The family later moved to 7 Borve, which his father obtained in 1900. 

Allan became a fisherman and yachtsman, crewing on the Vita. In 1908 he married Mary MacLeod of Trealigarry, with whom he was to have seven children. 7 Ruisgarry was passed to Allan following his father’s death in 1915.

Allan's daughter Rebecca contributed a recording to the sound archive of the School of Scottish Studies, University of Edinburgh, in which she recounted the tale of her father incorporating driftwood into his new house. The recording is available here on the Tobar an Dualchais website.