This paper investigates the demand for private health insurance in Italy, where universal public coverage coexists with high out-of-pocket healthcare spending. Using data from the Italian Survey of Consumer Expectations (ISCE) and a structured willingness-to-pay (WTP) elicitation method, we identify key drivers of WTP. These include income, perceived health risks, prior medical expenses, attitudes toward the public health system and existing health or other insurance policies. All of these are positively associated with higher WTP, reflecting greater financial capacity, risk awareness, and trust in insurance mechanisms. Further, a randomized control trial reveals that providing information on the costs and (shorter) waiting times for private medical services increases awareness of out-of-pocket expenditure risks, raising WTP especially among the self-employed, and corrects prior misperceptions - whether optimistic or pessimistic - thereby aligning expectations with reality and fostering more efficient insurance choices.