The Isle of Wight Undercliff is a unique coastal landscape. Formed by deep-seated mass movement, the origins of the Undercliff can be traced back through the Holocene and Late Quaternary, when sea level and climatic conditions were very different than today. The spectacular landscape of stepped terraces with open sea views, coupled with a warm humid micro-climate, became popular in Victorian times, a period of rapid development of Ventnor and other villages located within the Undercliff. The occupation and development of the Undercliff has exposed development and infrastructure to repeated damage from incipient ground displacement. Occasional more rapid ground movement and landslide events have occurred leading to the evacuation of residents, severe damage and abandonment of affected areas. This chapter gives an account of the landscape and landforms of the Isle of Wight Undercliff as observed from Victorian times to the present day. It presents new work to construct a three-dimensional model of the underlying geology which has a profound influence on the various landslide ground models that form the Undercliff. The sustainability of development and continued occupation of the Undercliff gives rise to many challenges and risks that requires effective management of land instability to mitigate the potential economic losses, which are anticipated to increase in future due to climate change and rising sea level.