Speaking Of Travel ®

What if planning your next adventure felt more like a conversation with a trusted friend than a checklist? In this episode of Speaking of Travel, I’m joined by Anna Jaffe and Harriet Brown of Mobi.AI, a powerful new platform reimagining travel planning through the lens of empathy, technology, and storytelling. This is more than a travel episode. It’s a love letter to curiosity, to wandering with purpose, and to a future where your travel tools know you crave hidden bookstores just as much as beach sunsets. Together we explore how AI is helping travelers find what really speaks to them beyond the filters and search engines and how this deeply personal approach is changing the way we explore the world. Anna and Harriet share why travel planning is so complex and so human and how AI tools are learning what you love and helping you discover more of it. This is a conversation about possibility, connection, and the beautiful future of travel where technology listens, learns, and helps us find joy in the journey. So