With the Soviet occupation of Estonia, Gailit fled with his family in September 1944 to Sweden, where he worked as a writer.

[3] In 1917 August Gailit, along with some other writers and poets, founded a literary group called "Siuru" with which their erotic poems caused some scandal.

Members of the group included: Marie Under, Henrik Visnapuu, Johannes Semper, Peet Aren, Friedebert Tuglas and Artur Adson.

His famous novel Toomas Nipernaadi (which was made into a movie in 1983) describes the romantic and adventurous life of a vagabond.

Gailit's novel Üle rahutu vee (published in 1951 in Gothenburg, Sweden) concerns the tragic event of having to leave one's homeland.