Drawing from ethnographic research and interviews with older North American women who migrated alone to retire in Ecuador, this article grows the body of literature on gender and ageing, examining how these women position themselves within a gender-ageing nexus, contradicting certain gender norms in their attempt to obtain later-life self-fulfilment. Particularly, we examine how this group positions the third age as a time of individual adventure and self-actualisation, challenging normative gender ideals about femininity and care but meeting (many) social expectations to “age well.” We argue that the lifestyles of these women demonstrate new experiments with gendered ageing, facilitated by global inequalities but challenging some normative ideals around femininity and old(er) age.