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Join Matthias Keller, Chief Product Officer at KAYAK, and Adam Harris, CEO of Cloudbeds, in conversation with Skift’s Head of Research Seth Borko, as they explore how AI is transforming how we search, book, and personalize travel. We’ll explore: Whether the “tyranny of the search box” is ending—and what smarter, more conversational search could look like. Why Kayak launched Kayak.AI and how it compares to broader AI platforms like Gemini and ChatGPT. The shift from keyword-driven discovery to context-aware, personalized travel recommendations. How travel intermediaries are evolving in an AI-first world—and who may ultimately “own” the customer relationship. How personalization is being implemented at both the booking engine and property levels. The role of vertical vs. horizontal AI in shaping the future of travel discovery. The data readiness gap in hospitality—and what needs to change to unlock the full potential of AI. Ethical challenges around AI in travel: personalization vs. privacy, trust, and what the line is between helpful and intrusive. Connect with Skift LinkedIn: / skift WhatsApp: https://whatsapp.com/channel/0029VaAL... Facebook: / skiftnews Instagram: / skiftnews Threads: https://www.threads.net/@skiftnews Bluesky: https://bsky.app/profile/skiftnews.bs... X: / skift Subscribe to @SkiftNews and never miss an update from the travel industry.