This paper closely examines fairy tale films with road movie components, in particular those films featuring female protagonists. The study’s objective is twofold: first, to further develop existing research on the road movie by exploring one of the lesser known constituents of this broad genre and, second, to address gaps in scholarly literature on road movies when it comes to themes in female-led trips and the characterization of travelling females. Through a detailed analysis of the journeys of female characters in recent voyage-oriented fairy tale films—Peter Pan (P.J. Hogan, 2003), Alice in Wonderland (Tim Burton, 2010) and Tangled (Byron Howard and Nathan Greno, 2010)—the investigation shows that these new heroines significantly differ from those of old. Their travels are portrayed as being less difficult, and the traits that they exhibit while on the road, namely fearlessness, rationality and an undying optimism, are rather favourable when compared to those exhibited by former road heroines. Although these protagonists still face characters who wish to impede their movement away from a domestic setting, it is demonstrated that the protagonists are ultimately successful in not only acquiring power in the surroundings that they find themselves in, but also in carrying over their goals and dreams to their own worlds upon their return, privileges that most former road heroines did not have. Ultimately, the study shows that females can be as efficient travellers as males, and in some cases are portrayed as even more competent than their male counterparts.