The rise of AI travel agents presents both exciting prospects and significant unknowns for the hospitality sector. Key questions remain around the financial models for personal agents, the future of venue discovery in an agent-first world, and the establishment of trust and identity verification for autonomous agents. This article explores these uncertainties, including the regulatory landscape for AI-driven commerce, data privacy concerns, reputation management for AI agents, and the impact on service quality and market concentration. Understanding these challenges is crucial for venues preparing for an agent-ready future, ensuring they can effectively connect with AI agents and optimise their offerings for orchestrated trips and coordinated bookings.