Aim: The research sheds light on the challenges and limitations of Spanish and Italian hospital design by looking at the gaps between education and practice. Background: Hospital design plays an important role in providing high-quality and cost-effective facilities for any healthcare system. Spain and Italy face contemporary challenges (i.e., elderly population, staff retention, and obsolete healthcare facilities) and have similar issues of life expectancy, health expenditure, hospital beds provision, and decentralized tax-financed healthcare systems. Method: A cross-sectional, mixed-method study was used. This involved two different data collection strategies and analysis for each area of investigation: (i) education and (ii) practice. For the former, educational programs were reviewed via a web search; for the latter, an online survey of 53 architectural/engineering offices involved in hospital design was conducted. Results: Hospital design education is limited to 0/58 in Spanish and 2/60 courses in Italian universities, although each country offers three postgraduate courses. The practitioners’ survey shows that even though their offices have a long history of healthcare design, only 48% in Spain and 60% in Italy have received specific university training. Office staff lack employees with medical backgrounds, which hinders any partnership between health and design fields either for design practice or the education fields. Laws, national regulations, technical guidelines, and previous experience are the most useful information sources, while international scientific publications appear underused by practitioners. Conclusions: Italian and Spanish healthcare architecture could be improved by promoting multidisciplinary teams (in practice and education) and improving the education offer by tailoring it to national needs.