This chapter focuses on a visit by two women activists and travellers to the Soviet Union in the 1960s. The chapter analyses the left-leaning feminist Rosey E. Pool’s private letters in which she describes her travel experiences with her partner Ursel ‘Isa’ Isenburg behind the Iron Curtain. In a reading against the grain, the chapter uncovers the multiple layers of meaning in the seemingly partisan accounts of a fellow traveller. Pool’s contemporary notes provide the reader with a very subjective take on Khrushchev’s USSR that owed little to other travelogues of the time. The chapter interprets the letters as commentary on Western political issues, such as women’s liberation and racism in the American South.