Can AI plan a family holiday?+
It is genuinely good at the hard half: arbitrating between people who want different things, pacing a day around the naps, meals and attention spans you describe, and building contingencies. Those need no facts it does not have. It is unreliable at the half that ruins a day with children: opening hours, prices, closing days, buggy access, baby changing, high chairs and under-five policies. Have it produce the plan and the list of things to verify, then verify them yourself.
How do I stop an AI itinerary being unrealistic for kids?+
Plan hours, not sights. One anchor per day chosen by one person, with two or three nearby optional things that can be dropped without anyone feeling cheated, and count the real hours door to door: the forty minutes it takes to get a family out of an apartment, the queue, and lunch taking an hour rather than twenty minutes. Give the model your actual getting-ready time and the hour the day falls apart, and instruct it to cut a day rather than compress it.
How do you keep everyone happy on a family trip?+
Everyone, children included, names one non-negotiable for the trip: one thing that is definitely happening. A seven-year-old who knows the swimming pool is on Thursday tolerates Wednesday's cathedral. This is the structure an AI can actually enforce, because it is a constraint-satisfaction problem, and it is the single biggest improvement most family trips can make. Instruct it to tell you if the days cannot fit everyone's one thing.
What documents does a child need to travel abroad?+
This is the question that stops families at the gate, and it is the one never to settle in a chat window. Depending on the countries involved, a child travelling with only one parent, with grandparents, or with a different surname from the accompanying adult may be asked for a consent letter from the other parent, a birth certificate, or evidence of the relationship. Children normally need their own passport, and some destinations require validity beyond your return date. Airlines apply their own rules on top of the country's. Confirm with the airline and the destination country's embassy or consulate, early enough that a missing document is fixable.
Can I trust AI on whether a place is buggy friendly or has baby changing?+
No. Accessibility and facilities are the details a day with a toddler turns on and the ones a model is least reliable about, because they change and are rarely well documented. Treat every claim about lifts, step-free access, changing tables, high chairs and age policies as something to check with the venue directly. The phrase family friendly is worth ignoring entirely: it means nothing, so ask about the specific thing you need instead.
Can I ask AI about food allergies when travelling?+
Not for anything you will act on. Allergen information, ingredients and what is safe for your child to eat abroad come from a translated allergen card from a reliable source and a conversation with the restaurant, every time. A model translating an ingredient list or guessing at a local dish is a risk with no upside.
What should I plan before the trip goes wrong?+
With children, disruption is a certainty rather than a possibility, so build the contingencies in advance: a wet-weather alternative near each day's anchor, what the day becomes if one adult has to stay in with an ill child, what happens if you arrive and cannot get in, the reduced version for when the morning has already gone badly, and which day absorbs a travel delay. Twenty minutes of this is the most useful preparation you will do.
How do I install the Tom Family Travel Planner skill?+
The download is a ZIP with SKILL.md at the root of the archive, not inside a nested folder. In the Claude desktop app open Customize then Skills, upload the ZIP and toggle it on. Skills need code execution enabled, under Settings then Capabilities. Anthropic's help centre currently lists Skills on Free, Pro, Max, Team and Enterprise, while its Academy tutorial lists Pro, Max, Team and Enterprise, so if you are on the free plan check Settings then Capabilities for your own account rather than trusting either page. In ChatGPT or Gemini, paste the contents of SKILL.md into custom instructions instead.
