This chapter briefly explores the rich tradition of literature written and published by women in the Spanish Antilles, Cuba and Puerto Rico, in the nineteenth and first half of the twentieth centuries. It focuses on the ways these women engaged with their countries' distinctive island identities from a political and gendered perspective within the broader framework of the Hispanic literary and cultural tradition. The genre most cultivated by women was poetry, although the most celebrated woman writer of the period, the Cuban Gertrudis Gomez de Avellaneda, was acclaimed as a dramatist as well as a poet, and wrote novels and an autobiography. The Spanish Constitution of 1837 guaranteed freedom of the press, and it was during the progressive General Espartero's regency that Avellaneda's novel, Sab, and her first book of poems, Poesias, were published. Sab remains exceptionally transgressive for its times.