What if people could plan trips the way they naturally think, using freeform, associative fragments, and the system could intuitively structure it for them?
🚨 Problem
Today’s trip planners largely fail to align with how people naturally conceive travel.
Early-stage planning is typically narrative, intuitive, and sequential. People think in stories, such as "Fly to location, explore, eat good food," rather than in structured fields and forms.
Most applications force users into strict templates and workflows from the outset, limiting spontaneity and introducing unnecessary cognitive friction. The resulting outputs, often static lists or rigid tables, fail to provide spatial or temporal visualization, making it difficult for travelers or their loved ones to truly understand the shape and rhythm of the journey.
This absence of spatial storytelling creates two major barriers: it reduces the sense of joy and momentum during the planning process, and it limits the emotional shareability of the final itinerary.
📝 Task
FlyBy set out to minimize cognitive load at the point of entry by allowing users to express plans as they would in everyday conversation. At the same time, it aimed to dynamically structure and visualize these plans into intuitive, interactive story maps that provide a clear spatial and temporal understanding of the journey.
Designing for this mission required creating a system that could:
Accept freeform, natural input
Intelligently apply lightweight structuring without requiring user intervention
Support progressive addition of details as needed
Visualize journeys in a way that resonated emotionally and spatially
The broader ambition was to design a flexible, cognitively intelligent system that could ultimately scale into adjacent domains beyond travel.
🎯 Action
FlyBy rethought the travel planning experience by applying principles from cognitive load theory, systems design, and interaction design.
Rather than presenting users with fields and forms, FlyBy invites users to type or voice dictate their plans naturally, as they would when speaking to a friend.
For example, a user might write.
"Flight to Miami at 3 PM, brunch at XYZ Café, drive to Key West."
This approach lowers entry barriers and preserves the momentum of creative thought.
Automatic Categorization
FlyBy automatically categorizes trip components (Flights, Hotels, Activities, Transport) while allowing users to add extra details dynamically, like flight numbers, reservation links, or notes, only when needed.
Seamless Sharing for Loved Ones
Once the trip is planned, users can generate a shareable link that lets friends and family see a clean, interactive map-based itinerary, so they get a real sense of the journey instead of just a text list.
Once plans are added, FlyBy transforms them into an interactive story map. Locations are plotted, routes are drawn, and a timeline is built, making it easy for loved ones to visualize the trip at a glance.