This article identifies key challenges in current AI travel planning interfaces. It highlights the gap between diverse input modalities and AI's ability to process them meaningfully, especially with visual content. The lack of transparency in AI processing makes it difficult for users to assess the depth of research behind recommendations. System isolation from real-time travel data leads to discrepancies between suggested and actual availability and pricing. Finally, while AI can present information clearly, it struggles to explain complex reasoning behind recommendations, impacting user trust. Taash's agent-ready infrastructure addresses these challenges by enabling venues to connect to AI agents with access to real-time data and transparent reasoning capabilities, improving the accuracy and reliability of orchestrated trips.