Millions of blind people cannot use travel sites effectively due to the significant access and usability barriers. Literature recognizes that travel sites lack accessibility and usability, but does not clarify the nature of interaction challenges blind users face. We conducted an exploratory field study with blind participants to examine where, how and why challenges arose in searching for flights on the Orbitz travel site. We employed verbal protocol analysis to generate an in–depth, contextually–situated and experiential understanding of participants’ interaction challenges. Results establish the feasibility and utility of our approach for an accurate evaluation of accessibility and usability of travel sites for blind users.