The collapse of socialism in central and eastern Europe and the transition to market-based democracies has had far-reaching effects on many aspects of environmental policy and management. This paper discusses key issues for nature and landscape conservation in the light of this transition and the likely enlargement of the European Union to include former socialist states. Case studies from two contrasting models of former socialist polities – the Czech Republic and Slovenia – highlight the need to analyse the current transition in the light of specific historic trajectories. Nevertheless, despite clear differences between protected area systems and their management in the two countries, clear commonalities relating to post-socialist transition emerge – notably in relation to issues surrounding land ownership, new structures of state power, and developments in civil society. These issues are then discussed in relation to further likely transitions as the two countries seek to join the European Union.