In a fascinating real-world test of AI capabilities, a couple recently pitted OpenAI’s ChatGPT against Anthropic’s Claude to plan their vacation to Lisbon, Portugal. The experiment, detailed in Business Insider, revealed striking differences in how these leading generative AI models approach travel planning. While ChatGPT delivered a comprehensive itinerary with specific restaurant recommendations and detailed daily activities, Claude took a more philosophical approach, focusing on the emotional experience of travel and encouraging spontaneity.
The results highlight the distinct personalities emerging in today’s AI assistants. ChatGPT functioned like an efficient travel agent, providing practical, actionable advice with specific locations and times. Claude, meanwhile, operated more like a thoughtful travel companion, emphasizing the importance of unplanned moments and suggesting the couple leave room for serendipitous discoveries. This real-world comparison offers valuable insights for travelers considering AI assistance for their next trip planning session, while also showcasing how different AI models can produce dramatically different outputs even when given identical tasks.
Perhaps most interestingly, the couple found value in both approaches, ultimately creating a hybrid plan that incorporated ChatGPT’s structured recommendations while embracing Claude’s emphasis on flexibility. This experiment demonstrates that the future of AI assistance may not be about finding the ‘best’ model, but rather understanding which AI personality aligns with specific needs and preferences for different tasks. As generative AI continues evolving, users may increasingly select different models based on their distinct approaches rather than purely technical capabilities.
Source: https://www.businessinsider.com/used-chatgpt-plan-trip-my-partner-used-claude-2025-10