Travel Smart during Holidays

Overview

Vacations Unlocked was a 2025 hackathon project where we prototyped an AI-powered trip planner that could turn a traveler’s loose intent into a concrete, bookable trip. In a few days, our team built a conversational “smart trip” experience that used Expedia's supply and loyalty context to suggest destinations and stays. Essentially an early, scrappy proof of concept for what later became the Smart Trip AI product direction.

Hackathon 2025

Stage

XD / Eng

Stakeholders

3 days / June 2025

Timeline

Problem

Travelers often miss opportunities to maximize their vacation days because combining national holidays with personal time off requires manual effort, searching online, checking calendars, and piecing together dates, making trip planning time-consuming, frustrating, and less inspiring.

OUTCOME

Vacations Unlocked laid the foundation for Smart Trip AI.

What began as a hackathon concept helped shape a more personal, conversational way to plan travel, making it easier for travelers to discover experiences that fit them, while helping partners connect trip inspiration with loyalty.

This work was carried through from discovery to delivery, shaped through multiple rounds of iteration, and is slated to ship in Q4 2026.

If you enjoyed the video and storytelling behind Vacations Unlocked, feel free to reach out. I’m happy to share more.