This pilot study is pointed to establish the camaraderie between Artificial Intelligence, Hotels, and holiday travellers to Goa and deduce a research agenda that will guide in augmenting customer experiences through various phases of a planned holiday. Based on the literature review, the need to develop a research agenda to establish an evidence-based relationship between AI and Goan (Indian) hotel industry was identified and, a pilot study with 101 respondents was executed. The hypothesis covered the various phases of a holiday like planning, reservation, check-in, dining, and stay experience and the demography. The preliminary results suggested a positive contribution of artificial intelligence in effective holiday planning, execution, and management. To reinforce the pilot results and come up with a model for designing optimized customer experiences, a full-length study is planned