The transition to a circular economy (CE) is a critical component of achieving global climate and sustainability objectives. Yet, this transformation demands more than political commitment—it requires deep structural changes in organizational models and practices. While the literature on CE and sustainable business practices is expanding, regional-level empirical studies remain scarce, particularly those that compare different economic sectors and examine the gap between environmental awareness and actual implementation. This chapter presents the results of a survey conducted with 67 organizations in the Setúbal district, Portugal, assessing their readiness for CE adoption. The analysis focuses on three core dimensions: organizational awareness and implemented practices, sectoral differences between industry and services, and the key barriers to circular transformation. The findings highlight a clear discrepancy between awareness and action, sector-specific challenges, and recurring obstacles such as limited financial resources, lack of technical expertise, and organizational resistance. These insights offer practical guidance for regional policymakers, higher education institutions, and business leaders aiming to promote sustainable transitions through more effective, context-sensitive strategies.