Technologies have dramatically transformed tourist experience. However, research has largely focused on traveler attitudes and technology adoption rather than their experience with travel technologies. Taking a cross-country perspective, this study examines the role of technology readiness (TR) as a personality trait in shaping travelers’ satisfaction with travel technologies, using airlines as a case study. Results of an online survey of travelers in Australia, China, and the United States revealed the moderating effects of the TR dimensions of optimism and innovativeness as well as country of residence on the relationships between perceived quality of technology-enabled services (TESs), satisfaction with TESs, overall satisfaction, and future behavior. These relationships were stronger among travelers with higher TR and varied across countries. The results suggest that tourism and hospitality service providers should incorporate measures of traveler TR and TESs’ performance into their customer-experience monitoring system.