Travel planning can be overwhelming, with endless options and a desire for unique experiences within our budgets. Therefore, the author decided to test the generative artificial intelligence of Chat GPT-4, Open AI’s chatbot, to help plan travel for two alter egos. The bot performed well in finding family-friendly trips, suggesting luxury resorts with kids clubs and complimentary activities. However, it struggled to find mental health retreats within a $750-per-night budget and came up with generic responses for avoiding crowds in Europe. The bot’s recommendations can foster a sense of discovery, but ultimately, it is best to trust human travel professionals. Despite the limitations, the chatbot can serve as a preliminary planning tool, particularly for those seeking off-the-beaten-path experiences.