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Portugal is commonly recognized as one of the best drug policy examples in the world. Nonetheless, contrasts between drug use risks in rural vs urban settings in the country is an understudied topic, even if its specific challenges are commonly affirmed, both by professionals and people who use drugs (PWUD). The aim of this study was to compare rural and urban environments concerning socio-sanitary services availability; illegal drugs availability; risk behaviors related to drug use; stigma associated with illicit drug use; and social support. Additionally, specific harm reduction challenges and recommendations for improvement were explored. A qualitative study with two focus groups involving people who use drugs, outreach workers and local decision-makers was conducted. Distinct scenarios and challenges in both settings were found: In large cities, a significantly higher specialized service coverage than in rural areas was described. In rural settings, a higher number of drug-related risks, higher levels of stigma and lower availability of human and material resources were mentioned, although being associated with higher levels of informal social support and more proximal relationships with harm reduction teams. This study emphasizes the need for a harm reduction paradigm strongly focused on environmental risk determinants, as much as in individual ones.