Abstract: This paper examines the perspectival vision and funereal imagination underlying early English picturesque gardening through a study of the grotto and gardens at the Twickenham villa of the eighteenth-century English poet Alexander Pope. This paper challenges the view that Pope's English landscape garden rebelled against Continental traditions. Instead, it argues that Pope adapts and reinterprets religious and spiritual traditions embedded in Renaissance perspectival vision through a funereal imagination, thereby offering a critique of the increasingly influential scientific, secularised, and commercialised culture of landscape spectatorship in the eighteenth century. The analysis focuses on two spatial-visual routes: first, the perspectival vista extending from the Thames through the grotto and arcade of trees towards the shell temple; second, the reverse viewing of the same axis. Utilising seventeenth- and eighteenth-century textual and visual sources on perspectival vision, as well as Pope’s letters, poetry, and portraits, the paper argues that the grotto, arcade of trees, dim light, and perspectival structures together constituted an initiatory mode of seeing grounded in an awareness of mortality. Placing a “melancholic veil” over “Alberti’s window”, this mode of seeing expressed scepticism towards Renaissance confidence in mathematical geometry to reveal truth. Instead, through concealment, deferral and symbolism, it directed viewers towards the limits of human knowledge and the transience of life, creating a poetic space for reflection on existence and death.