Change has engulfed the coastal fringe of Australia. In balancing the built and natural environment, community needs, cultural significance and economic sustainability, planners aim to improve quality of life and create vibrant communities. Yet managing place change, particularly in coastal areas, is fraught with tensions. Most planning discussions about the rapidity of change, the impact of the Sea Change process and increased development have focused upon the extensiveness of residential expansion and the housing styles that challenge the essence of the character of these coastal towns. Character and sense of place qualities are the very reasons that sea changers desire to engage with and reside within these communities. One aspect missing from this discussion and analysis is the impact that large-scale transformations of iconic buildings are having upon these places. This paper examines the consequences that major commercial development projects have upon the communities of Sorrento and Queenscliff. It considers changes (proposed or realised) to four landmark historic hotels: The Koonya and Continental in Sorrento; and the Ozone and Vue Grand in Queenscliff. This paper focuses on issues of planning, social engagement and community debate.