Planning Together

The survey asked eight people about their most recent group trip: who they planned it with, what they used to keep track of it, and where it became difficult. The trips ranged from two people to six, planned with partners, family, or friends.

Key findings:

• Every group planned in a messaging app and kept the details somewhere else, and that second place never held. One saved links in a notes file that could not take video, which was where most of their ideas were coming from
• Chat was the easiest place to plan and the hardest place to finish. It kept every message, but never produced a version of the plan the group could point to
• Privacy was described as helping collaboration rather than blocking it. One respondent liked that her partner could not see everything she had saved, because some of it was meant to be a surprise, and she was still planning the trip with him
• One respondent used ChatGPT for a first plan and found it quick but generic. Another wanted help turning the Instagram posts she had already saved into something organised, rather than help deciding where to go
• Effort was rarely shared evenly. Several described one person planning while the others waited to be told, and one said plainly that each person should carry their own share

The observation ran across two sessions several weeks apart, and the group kept planning in their chat the whole time, so those messages were part of what I studied. The findings below come from all of it together. The survey had described planning as an orderly sequence, from the first idea to a destination and then to dates. The group worked the other way round, and the plan took shape while they browsed rather than before.

Key findings:

• Planning started with availability, not a destination. Work schedules, graduation dates, and cheaper weekday flights had fixed four days in June before anyone said where they wanted to go
• Constraints came next and cut the options down before anyone talked about what they wanted. Visas ruled out everywhere outside the Schengen area, an expected heatwave ruled out Italy and Spain, and student budgets ruled out Denmark
• Preferences formed while browsing rather than before it. The group did not know what they wanted from Ireland at the start, and highland cows, a flea market, and a walking tour became things they wanted only after someone found them
• Everything happened on phones, and a phone shows one person at a time. Sharing meant reading a screen aloud or handing it over, so whoever held it decided what the group saw
• Six people agreed to look for accommodation and two did, so the group chose from a far smaller set than it could have. One place they liked was booked by someone else while they were still deciding
• AI never came up once. When I offered to hand their material to ChatGPT for a plan, they turned it down, because searching was the part they enjoyed

In every case the group already had what it needed. What it did not have was a way to see it together.

I reviewed ChatGPT, Trip.com AI Trip Planner, Wanderlog, Roadtrippers, TripAdvisor, and Google Travel by planning a trip in each the way the observed group had, starting with no destination and working through to travel and accommodation. Each was judged on whether it can be used before a destination and dates are set, whether several people can contribute to the same plan, whether AI output can be edited in place or only regenerated, and whether it works properly on a phone.

Every platform runs on a phone, and that was the only requirement all six met. None of them let a group contribute to, discuss, and revise the same plan while it was still being formed. The opening was not a missing feature. It was a missing shared view.

Six friends have four days in Dublin and one week to plan it. The scenario follows Sara deciding what to keep private and what to share, Mia adding straight away while two others add nothing at all, and Tom sharing a plan generated by ChatGPT.

Two things the scenario settled:

• The choice between keeping something private and sharing it belongs at the moment of saving, not earlier. Sara only knew the café was worth sharing when she looked at it again the next day
• Contributions should be visible inside each category rather than on a separate summary page. The group only noticed what was missing at the moment it sat down to compare accommodation

Four colours, one typeface, and a fixed set of spacing values. Together they made it possible to rebuild the app twice without having to redesign it each time.

Typeface: Plus Jakarta Sans. Weights 400 to 800.

The app opens by asking for the name the group will see, then drops you into your own space, where everything you save sits in categories only you can see. You can start a group trip whenever you want, but nothing forces you to, because people collect ideas long before they agree to travel anywhere. Saving accepts a link, a note, an image, or a video, but only one kind at a time, and the choice between keeping something and sharing it comes at the end, followed by a screen naming exactly who will be able to see it. Inside a trip, the private and shared spaces are kept visibly apart, with a lock icon on the private one and a different background colour behind each. Every category shows who has contributed and who the group is still waiting on, and the assistant sits in its own tab with three suggested questions.

Not everything from the research made it into this version. Showing who had contributed stayed a simple marker inside each category rather than becoming a feature of its own. And the idea of asking a group to record its limits before searching was not built at all, because there is nowhere to record them until a shared space exists. The other five members were simulated, so one person could work through the whole group flow alone.

All three took part in the same session and worked through the scenario together, since the app is built for a group and their disagreements were part of what I wanted to see. They set up a profile, saved something without sharing it, created a trip, shared the item, and looked for where the group would discuss accommodation.

Saving changed the most. A title, a link, a note, and a photo now go into one entry together, so a saved link comes with a name and a description instead of only a web address. Items can sit in more than one category, and the categories themselves can be renamed, added to, or removed, so a group can shape them around its own trip. Food was added and travel was renamed transport. The private space moved below the group's and gained a lock, so it is obvious which one you are looking at.

Conversation was brought together rather than adjusted. Comments on individual items were removed, and everything now happens in a single discussion per trip, named after the trip, because with two places to talk nobody could remember which one a conversation had happened in. The assistant was narrowed rather than removed, since the objection had been to what it was deciding rather than to its existence. It now answers practical questions using what the group has already entered, and says when it does not have enough information instead of guessing.

The last change was one nobody had asked for. The first version could not tell a suggestion apart from a settled decision, so items could now be marked as decided, showing who decided, alongside a countdown to departure and a progress line for each category.

In the first round the three participants explained the interface to each other, so it was hard to tell what the design was saying on its own. The second round was run individually for that reason, with one person who had used the first version and one who had never seen it.