This chapter explores how Havana’s slave-owning elites employed the newspaper to articulate the dreams and aspirations of a modern Havana at the turn of the nineteenth century. The text looks closely at the plantocracy’s early writings on the city from the 1790s to the 1810s. It details the planters’ growing discontent with the urban aesthetics of the Spanish-Bourbon city and an impetus to replace it with one they called buen gusto (good taste). Buen gusto is examined here as a criollo elite discourse that speaks broadly to the aesthetics of Western modernity. Such discourse was instrumentalized to envision a modern Caribbean metropolis under the cultural regimes of Spanish colonialism and Atlantic slavery. All told, the chapter considers how the plantation system generated an aesthetic discourse that fueled future projects of urban expansion and renewal.