The tourism industry is highly complex and is deeply embedded into the social, environmental, and cultural fabric of social-ecological systems. Engaging in tourism presents an alternative rural development pathway for viticultural landscapes to diversify their economies and strengthen resilience at both micro (individual/business) and macro (community/regional) scales. In an Australian context, expansion of the tourism industry is identified as a key strategy for rural development, particularly as the viticultural industry responds to fragilities in the wine market and global export challenges. However, the emergence and growth of the tourism industry also creates risks for how multifunctional landscapes are valued and subsequently managed. To better understand this complex relationship, regenerative development and place attachment literatures are explored to identify how landscapes and practices within viticultural regions can be best supported by tourism. Host and guest values are examined in two prominent Australian food and wine regions, McLaren Vale in South Australia and Margaret River in Western Australia. Both places have a history for driving sustainable and innovative practices across many facets of rural development and landscape management, which drive regional identity. However, a mismatch is emerging between local and visitor values towards a range of sustainable land use and development themes. Locals are valuing sustainable landscapes and agriculture more highly than visitors, which can in part be attributed to local connection to place. Meanwhile, visitors are less aware of the role that tourism can have in supporting sustainable landscapes and agriculture. Systems are required to adapt and respond reflexively to the evolving landscape of viticultural regions.