How to Use Claude as a Family Travel Planner: The Tom Skill Guide

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Skill · .md

The skill behind this guide: Tom - Family Travel Planner AI Skill. Holds your family profile between trips - ages, nap windows, what each of them will not tolerate, what worked last time - so the next holiday starts from the last one - $19, one payment, yours permanently.

View the Tom skill →

A model is genuinely good at the hard part of family travel, which is arbitrating between five people who want different things and building a day that does not collapse at four in the afternoon. It is bad at the part that ruins the day: it will tell you a museum opens at ten, has baby changing and lets under-fives in free, and be wrong about all three. This guide separates the two, and spends the most time on the thing nobody writes about, which is the paperwork for crossing a border with a child.

0:15 · loop Same AI, same question. One file makes it a specialist.

The two halves of the job

Task Verdict Why
Arbitrating what everyone wants into one workable week Genuinely good It is a scheduling and negotiation problem and needs no external facts
Pacing a day around naps, meals and attention spans you describe Genuinely good Arithmetic on constraints you supply
Building wet-weather and illness plan Bs Genuinely good Structure, not facts. This is the most underused thing on the list
Producing the list of things to verify, in the order to verify them Genuinely good It knows what usually matters even when it does not know your answer
Opening hours, prices, closing days, seasonal shutdowns Check every one Confidently stated, frequently out of date or invented
Buggy access, lifts, baby changing, high chairs, under-five policies Check every one The exact details a day with a toddler turns on, and the least reliable
Whether somewhere is "family friendly" Meaningless The label means nothing. Ask about the specific thing you need instead
Allergens, ingredients and what is safe for your child to eat abroad Never A translated allergen card from a reliable source, and the restaurant, not a chat
Passports, visas and consent letters for children Never See the section below. This is the one that stops you at the gate

The thing that actually stops families at the airport. Rules for children crossing borders are genuinely complicated and a model will answer confidently and sometimes wrongly. Depending on the countries involved, a child travelling with only one parent, with grandparents, or with a different surname from the adult accompanying them 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 it to be valid for a set period beyond your return date. Airlines apply their own rules on top of the country's. None of this is something to settle in a chat window: confirm it with the airline and with the destination country's embassy or consulate, and do it early enough that a missing document is fixable.

The pacing rule that actually works

Most family itineraries fail for a countable reason rather than a vague one. They plan sights, not hours, and the hours do not exist.

The fix is a rule you can apply without any local knowledge: one anchor per day, everything else optional. One thing the day is built around, chosen by one person, and a short list of nearby possibilities that can be dropped without anybody feeling cheated. Then count the real hours door to door, including the forty minutes it takes to get a family out of an apartment, the queue you did not plan for, and the fact that lunch with small children is an hour rather than the twenty minutes it is when you travel alone.

The second rule is about consent rather than logistics: everyone in the family, including the children, 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 that a model can actually enforce for you, because it is a constraint-satisfaction problem, and it is the single biggest improvement most family trips can make.

Prompt 1 - the family profile you reuse every trip

Help me write a reusable FAMILY TRAVEL PROFILE. Interview me one question at a time. Do not suggest any destinations. Cover: 1. Everyone travelling: ages at the time of the trip, and for the youngest, nap timing and whether they still sleep in a buggy. 2. For each person, the thing they will not tolerate. Be specific: queues, early starts, long car journeys, walking, museums, heat, being hungry. 3. For each person, one non-negotiable they would want on a trip. 4. Eating: what the fussiest eater will reliably accept, and any allergy or dietary requirement, recorded as a fact I will verify locally rather than something for you to advise on. 5. Our actual pace: how long it takes us to leave in the morning, and what time the day falls apart. 6. What went wrong on the last trip, and what worked. Write it back as a one-page profile I can paste into any future planning conversation. Mark anything I was vague about, because that is what I will get wrong again.
Skill spotlight
Tom - Family Travel Planner AI Skill
Tom - Family Travel Planner AI Skill
$19this skill

Keeps the family profile between trips, which is where the value is: children age a year between holidays, and the plan that worked when the youngest was two is wrong when she is four. Built to plan one anchor a day, count real hours, and mark every local fact as something for you to verify rather than stating it.

View Tom - Family Travel Planner →

Prompt 2 - a day plan that states no facts

Build day plans for [DESTINATION], [N] days, using the family profile below. Structure, per day: - ONE anchor, and whose non-negotiable it satisfies - two or three optional nearby things, explicitly droppable - where the meal breaks fall, given our eating times - the recovery slot: when we go back, swim, or do nothing - total hours out of the door, counted door to door, including our real getting-ready time Hard rules: - State no opening hours, prices, closing days or booking requirements. Write [VERIFY] beside anything that depends on one. - Make no claim about buggy access, lifts, baby changing, high chairs or age policies. Write [VERIFY] there too. - Do not use the phrase family friendly. Name the specific thing that matters instead. - Every person in the profile must have their non-negotiable somewhere in the week. Tell me if the days cannot fit them all. - If a day exceeds the hours we can actually do, say so and cut it rather than compressing it. FAMILY PROFILE: [PASTE]

Prompt 3 - the verification list, in the order to do it

This is the prompt that converts an unreliable draft into a usable plan. The model does not know your answers, but it does know which questions matter and which ones are expensive to get wrong.

Take the plan below and produce a VERIFICATION LIST. Supply no answers, only questions. Group them by: - book or reserve now, because it sells out or the price moves - check this week, because getting it wrong costs us a day - check the day before, because it changes - check on arrival For each item: exactly what to ask, and who to ask - the venue, the airline, the accommodation, the transport operator, an official tourism or government site. Where a venue's own page is the only reliable source, say so. Flag separately anything that would break the day entirely if it turned out to be false, and put those first. End with the three things families most often forget to check for a trip of this shape. PLAN: [PASTE]

Prompt 4 - plan B, before you need it

The most useful twenty minutes you will spend, and the thing almost nobody does in advance. With children the disruption is not a possibility, it is a scheduling certainty.

For the plan below, build the contingencies. Do not rewrite the plan. Produce: 1. WET WEATHER: for each day, an indoor alternative that is near enough to reach without a major journey. Mark each [VERIFY]. 2. SOMEONE IS ILL: what the day becomes if one adult has to stay in with one child. Which anchors survive being split. 3. CLOSED OR FULL: for each anchor, what the day becomes if we arrive and cannot get in. 4. TOO TIRED: the version of each day for when the morning has already gone badly. 5. THE TRAVEL DAY GOES WRONG: if we lose half a day to a delay, which day absorbs it and what gets dropped. For each, one line only, and name what we lose. Do not reassure me that it will be fine. PLAN: [PASTE]
Complementary prompt pack
Travel & Lifestyle Prompt Library
Travel & Lifestyle Prompt Library
$9this pack

The jobs around the itinerary - budgets, packing, multi-city routing, the admin before you leave - as ready prompts rather than a persona you load. Useful when the next trip is a different shape from this one.

View Travel & Lifestyle Prompt Library →

Where it fails

  • Live facts. Hours, prices, closing days, seasonal shutdowns, whether a place still exists. Stated confidently, often stale. Every one gets a [VERIFY].
  • Accessibility and facilities. Buggy access, lifts, changing tables, high chairs, under-five policies. These are the details a day with a toddler turns on and the ones it is least reliable about, because they change and are rarely well documented.
  • Allergies and food safety. Never from a chat. Use a translated allergen card from a reliable source and confirm at the restaurant, every time.
  • Child travel documents. Consent letters, passport validity rules, evidence of relationship. Airline and consulate, early.
  • Optimism about your family. Left alone it plans for a family with more stamina than yours. Give it your real getting-ready time and the hour the day falls apart, and hold it to them.
  • Distances. It underestimates how long anything takes with children, and it does not know the hill, the stairs at that metro station, or that the bus only runs hourly in September.
  • Insurance and medical cover. What is covered for a child abroad is a question for your insurer and your health service, in writing.

How do you install the Tom skill?

The download is a ZIP with SKILL.md at the root of the archive, not inside a nested folder - that folder structure is the usual reason an upload fails. In the Claude desktop app, open Customize → Skills, upload the ZIP and toggle it on.

Skills need code execution enabled, under Settings → 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 → Capabilities for your own account rather than taking either page's word for it. The full walkthrough is in the skill installation guide.

In ChatGPT or Gemini there is no upload step: open SKILL.md, copy the contents, and paste them into custom instructions. You lose automatic triggering and keep the method.

Who is this for?

Parents planning a holiday with children of any age, grandparents taking grandchildren, and anyone organising a trip where the group cannot all do the same thing. It works in Claude, ChatGPT or any AI chat.

The catalogue splits the travel jobs rather than bundling them, each a one-time download at $19:

The wider set is the travel, food & home skills, with ready-made prompts in food & home prompts.

In summary:

Let it arbitrate, pace and plan contingencies, because those need no facts it does not have. Make it state no fact at all about hours, prices, access or facilities, and have it produce the verification list instead. One anchor a day, one non-negotiable per person, real hours counted door to door. Sort the child travel documents with the airline and the consulate early, never in a chat. For the profile that carries between trips, Tom - Family Travel Planner AI Skill ($19); for the surrounding admin, the Travel & Lifestyle Prompt Library ($9). Both work in Claude, ChatGPT and any AI chat, with a 30-day money-back guarantee.

Skill · .md · Works with Claude & ChatGPT

Tom - Family Travel Planner AI Skill

One file that remembers your family between trips, plans one anchor a day around the hours you really have, gives every person their one non-negotiable, and marks every local fact for you to verify instead of inventing it. No subscription. Yours permanently.

$19
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Frequently asked questions

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.

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