Alto Salento is a territory blessed with natural resources, agricultural historical landscapes (century-old olive groves), valuable rural architectural and cultural heritage (i.e. masserie, trulli, underground olive mills, ancient trails). Thanks to the enduring efforts of local rural champions and animators, pioneer farmers, innovative neo-rural dwellers, environmental activists and committed local institutions, multifunctional farms (offering hospitality, educational and recreational services, on-farm direct selling, social farming activities) flourished in the past decades, especially in the Northern part, and the ‘turn to quality’ resulted into the diffusion of organic farming practices, increasing attention to preservation and enhancement of local ancient varieties, agro-biodiversity and local foods. In the South, where more production-centred dynamics are at play, significant investments were made to improve the quality and add value to key agricultural productions – olives, wine grapes, vegetables and dairy – through processing, protected origin and sustainable agriculture labelling and territorial marketing initiatives. Over time, portions of coastal and inland agricultural landscapes were protected through national or regional legal frameworks and precious rural built heritage was restored also thanks to EU funds, opening up promising windows of opportunity for the development of individual and collective initiatives of slow, sustainable and eco-tourism. Regular exchanges are in place between certain actors but collaboration is not widespread and only a few consolidated networks really operate in the territory. Different frameworks (e.g. Agenda 21, CETSs, Leader) provided opportunities for participatory visioning and planning, effectively engaging (at least temporarily) a significant number of actors. Advocates of conservation, sustainable and inclusive use of local fragile natural and cultural heritage denounce overexploitation impulses and elitist drifts associated to tourism development. Concerns have also emerged about the risk of diluting the message, losing authenticity and control, due to penetration of new actors, representing non-rural and non-local stakes, in local rural economy dynamics. The devastating spread of the deadly olive tree pathogen Xylella fastidiosa is now threatening the survival of century-old olive trees, a unique trait of the Alto Salento landscape, with uncertain solutions and prospects.