Building Wanderly in public — curated trip plans + a companion that stays with you
I’ve been building a travel product called Wanderly.
Most AI travel tools stop once the itinerary is generated.
I’m betting the more valuable part is what happens during the trip.
The idea
Wanderly combines:
Curated signature itineraries for the world’s most visited cities
(not generic live AI dumps — carefully written, calm pacing, strong day structure)
Juno — a quiet local-style companion that checks in during the trip, helps when plans change, and stays available if you need support
Dossier — one calm place for your documents, bookings, and trip logistics
The plan is the entry point.
Juno + Dossier are the reason to pay.
Why curated (for now)
I’m deliberately starting with high-quality hand-shaped itineraries for ~15 cities instead of wiring expensive live generation on day one.
For major destinations, taste, pacing, and neighbourhood logic matter more than endless AI novelty.
I’m treating the itineraries like editorial pieces rather than random outputs.
First city set is a mix of high-volume and slightly more niche destinations (London, Paris, Rome, Barcelona, Amsterdam, Tokyo, New York, Bangkok, Istanbul, Hong Kong + Lisbon, Prague, Florence, Edinburgh, Kyoto).
Users pick a style after choosing the city:
Classic highlights (first-timers)
Slower / more local
Food & neighbourhoods
Pricing direction
One-time $9 Trip Pass per trip
(not a subscription)
Unlocks the full plan + Juno during the trip + Dossier.
What I’m looking for feedback on
Does “curated plan + in-trip companion” feel more valuable than another pure AI itinerary tool?
Is $9 once per trip reasonable?
Any cities you’d swap in/out of the first 15?
Anything that feels unclear or weak in the positioning?
Happy to share more of the thinking. Building this solo / very small, zero-spend for now.
The interesting bet seems to be that the trip itself—not the planning—is where the recurring pain is.
Have early users actually relied on Juno or Dossier during a trip, and does that feel worth the $9?
Still working on the MVP, has not been launched for feedback yet!
Then the first useful test is probably whether travelers actually want the in-trip layer once they can use it. What are you planning to measure first?
Good question.
Since we’re still pre-launch, the first real test won’t be “did people use Juno a lot?” in the abstract — it’ll be more specific:
Do people unlock the Trip Pass after seeing the curated plan?
(Does the plan + the promise of Juno/Dossier feel worth $9 before the trip starts?)
Once they’re on the trip, do they actually open Juno or Dossier when something changes or they need support?
(Weather shift, closed place, “what should I do instead?”, documents, etc.)
After the trip, would they use it again or recommend it?
(That’s the real signal that the in-trip layer mattered.)
I’m treating the curated plan as the entry point, and Juno + Dossier as the reason the $9 feels justified.
So the first useful measurement is conversion to unlock, then actual in-trip usage of Juno/Dossier on real trips — even if the first ones are just friends or a small test group.
Happy to share what we learn once those numbers exist.
That’s a much cleaner test — especially whether Juno/Dossier usage actually justifies the $9 beyond the curated plan. Happy to compare notes as you get the first numbers. What’s the best email to reach you on?