Retirement is a life transition that has been relatively underexplored by geographers. In particular, mirroring other areas of academic and policy research, studies on retirement transitions and post-retirement experiences have been relatively sparse. Drawing on case studies from research in Hampshire and West Sussex (UK), this paper considers the challenges and issues surrounding the occupational cessation and retirement relocation of former farming couples. Utilising in-depth interviews, the paper explores how work-life histories may serve to intricately shape the geographies of retirement. It is seen that whilst family farming provided a shared occupation for couples, the respective gender(ed) roles and associated positionings in relation to farming served to differentially shape respective partner's experiences of, and adjustment to, retirement. In focusing on post-retirement experiences, the paper advocates a more temporally relational understanding of the geographies of older age which recognises how past places and identities are drawn upon in developing a sense of physical, social and autobiographical insideness in retirement spaces.