Income, Pto, Schedule → Actual Trips. Meet Roamie

Hi HN — I am building Roamie. It started from a simple frustration: planning travel with friends sucks.

We juggle 6–10 tabs, everyone has different budgets, PTO limits, school breaks, and nobody knows when they’re actually free. Every trip planning takes so much effort.

Roamie is an AI travel companion that aggregates your real-world constraints: income, budget, PTO, calendar, vibe, and preferred destinations and then automatically suggests the best dates to travel, finds real flight/hotel deals via our travel partners, and matches you with other people who want to travel on the same dates/destinations.

Technically, Roamie pulls from three layers:

- User context (income, budget, schedule, calendar events, home airport, leave days, preferences)

- Deal aggregation (our flight/hotel/activities partners APIs

- Match graph (we cluster users by travel windows + vibe + destination interest)

We are working on our MVP which will be a simple ai agent that asks 6–8 questions, generates a travel plan, and produces bookable links. Long-term, we want to turn automate that booking entirely, and turn travel planning into a deterministic optimisation problem instead of a stress-filled guessing game.

We’d love feedback on the product idea, retention concerns, and whether anyone has tried to solve the “PTO + budget + dates” constraint problem before. Happy to answer everything.