According to Edmund Molyneux, Sidney began work on the Old Arcadia upon returning from Europe in 1577 ‘before his further employment by her Majesty, at his vacant and spare times of leisure (for he could endure at no time to be idle and void of action)’ (MW 311), though there are suggestions that he was interested in literary pursuits somewhat earlier. During the 1577 embassy German poet Paulus Melissus proclaimed in verse ‘O, Sidney, renowned for your study of the Muses’, and sometime travelling companion Lodowick Bryskett mentions that Sidney was ‘with the Muses sporting’ during their earlier continental tour. By 1579 Daniel Rogers praises Sidne's accomplishments as a fellow poet and alludes to literary collaborations with Dyer and Greville. The following year, when he started the Defence, Sidney adopted the modest pose (wonderfully illustrative of sprezzatura) of having ‘slipped into the title of a poet’, and being ‘provoked to say something unto you in the defence of that my unelected vocation’ (MW 212). It should be stressed that Sidney nowhere signals an intention to become a published poet or live by the pen, but there is increasing evidence from the late 1570s onwards of his sustained experimentation with English versification and exploration of poetry's utility that went beyond the level of simple compliance with what was expected of a cultured courtier.

As Molyneux suggests, the Old Arcadia was composed during enforced leisure, a dilatory period in which Elizabeth repeatedly obstructed Sidney's plans for greater English support for continental Protestants and grew increasingly unwilling to assign Sidney to duties overseas due to her distrust of his evident popularity with foreign rulers. Sidney spent much of this leisure at his sister's house at Wilton. The political and intellectual community that developed at Wilton was hugely important in providing a physical and mental space away from court in which much of Sidney's writing takes shape. The immediate contexts of the Old Arcadia's production and reception at Wilton are described in the dedication to the Mary Sidney prefacing of the 1590 edition: