Research in sustainability transformations has emphasized technological innovation and large structural changes. Less attention has been paid to enabling approaches which emphasize the role of reimagination and collaborative exploration of alternative futures, involving agency, emancipation and care. In this research we took an enabling approach to sustainability transformations and worked with stakeholders in collaborative workshops to invite their experience of the COVID-19 pandemic and its transformative potential in envisioning and co-producing sustainable futures. In the workshops, stakeholders discussed their understandings of sustainable tourism development. What was evident among stakeholders was a caring for people—employees, locals, tourists. Although nature was another focus (often in the context of the new-found interest in tourism in proximate environments), care did not go all the way to redefine human and non-human relationship—missing a deep ecological understanding. This study expands knowledge on sustainability transformation and disruptive research that creates processes for re-imagination.