Travel planning has always contained a certain amount of administrative nonsense.
You may enjoy choosing where to go. You may be less enthusiastic about comparing seven train times, finding out whether a museum closes on Tuesdays and working out why one supposedly convenient hotel involves three buses and a substantial hill.
Artificial intelligence can help with that part.
Use of AI among travellers over 50 is already growing. AARP’s 2026 travel research found that the proportion using AI to find travel deals had doubled from 8% to 16%.
That does not make AI a travel agent, booking service or reliable source of current regulations. It is better thought of as a very fast planning assistant whose homework still needs checking.
Two Minute Read
- AI is particularly useful for generating itinerary ideas, comparing options and reducing planning workload.
- Tell it your real priorities: pace, budget, walking tolerance, interests and preferred amount of free time.
- Ask for several alternatives rather than accepting its first itinerary.
- Never assume opening hours, prices, transport schedules, visa rules or entry requirements are current.
- Verify important information on official websites before booking or travelling.
- Book through legitimate providers rather than unfamiliar links supplied by an AI conversation.
- A good AI-assisted itinerary should contain breathing room rather than simply more attractions.
Start by telling AI what kind of trip you actually want
A vague question produces a vague itinerary.
“Plan four days in Lisbon” might return the sort of schedule that assumes breakfast at seven, three attractions before lunch and a curious objection to sitting down.
Give it better instructions.
For example:
“I have four days in Lisbon. I prefer one major attraction each morning, a relaxed lunch, limited uphill walking and free time in the afternoon. Suggest a flexible itinerary rather than filling every hour.”
Now the tool has something useful to work with.
You can add:
- approximate budget;
- whether you prefer museums, gardens, food, history or scenery;
- whether you are travelling alone or with others;
- how much walking feels comfortable;
- whether you dislike early starts;
- whether public transport or driving is preferable.
None of this is particularly glamorous. It is, however, much more likely to produce a trip that suits the person taking it.
Ask for choices rather than one supposedly perfect answer
AI is good at generating alternatives quickly.
Instead of asking, “Where should I stay?”, try:
“Compare three types of neighbourhood for a visitor who values quiet evenings, walkable restaurants and easy public transport.”
Instead of:
“What’s the best day trip?”
try:
“Suggest three day trips: one focused on history, one on scenery and one requiring the least complicated transport.”
That turns the conversation into a decision-making aid rather than allowing the machine to make the decision for you.
It also makes dubious suggestions easier to spot.
Let it find the friction in your itinerary
One useful trick is to give AI a rough itinerary and ask it to criticise it.
You might ask:
“Which days look rushed?”
“Where have I allowed too little time between locations?”
“Which activities involve similar experiences that I could combine or remove?”
“Where could I add an unplanned afternoon?”
This fits particularly well with slower travel.
A good itinerary needs breathing room. Removing something can improve a trip just as effectively as discovering something new.
If you prefer deliberately comfortable pacing, our guide to making long journeys more comfortable after 50 also covers practical ways to reduce unnecessary travel-day strain.
Use AI for the first draft of a budget
AI can also be useful for identifying categories people forget.
Ask it to create a travel-budget checklist including:
- transport;
- accommodation;
- meals;
- local transport;
- admission charges;
- travel insurance;
- mobile data or roaming;
- tips where customary;
- airport transfers;
- contingency money.
Then replace estimates with current prices you have checked yourself.
This is an important distinction. AI is useful for remembering that airport transfers exist. It is less reliable for telling you precisely what one will cost next Thursday.
Currency values, fares and ticket prices change.
Never let AI be your final source for travel rules
This is where the division of labour becomes important.
AI can tell you what you need to investigate.
Official sources should tell you what the current rule actually is.
Entry requirements, visa rules, passport validity, vaccination requirements, driving regulations and safety advice can all change.
Everett’s Canadian perspective makes the Government of Canada’s Travel Advice and Advisories a natural example. Its destination pages cover safety, entry and exit requirements, health, local laws and other practical information. Travellers elsewhere should use the equivalent official government sources for their own country and destination.
Do the same with train operators, airlines, attractions and accommodation providers.
AI may have useful information about them.
The organisation itself knows whether the 09:42 train still exists.
Be cautious when AI sends you somewhere unfamiliar
Travel scams have become sufficiently convincing that a professional-looking website is no longer proof that a business is genuine.
The US Federal Trade Commission has published guidance on avoiding travel scams, including fake travel sites and scammers impersonating legitimate travel businesses.
If an AI tool suggests an unfamiliar booking site, do not assume the recommendation itself makes the site trustworthy.
Find the accommodation, airline or attraction through its known official website or a booking service you independently recognise.
Our guide to spotting an online scam before it costs you money is also worth reviewing before paying an unfamiliar travel business.
Particular caution is sensible if a seller insists on unusual payment methods such as cryptocurrency, gift cards or wire transfers.
Try asking AI to make your plan simpler
Most travel-planning technology is sold on the promise that it will help you discover more.
It can be just as useful for doing less.
Try:
“Remove two activities from this itinerary without losing the main experiences.”
Or:
“Rework this day so that there is a two-hour break after lunch.”
Or:
“Group these attractions geographically so I spend less time travelling between them.”
A machine has no emotional attachment to the fourth museum you optimistically added at midnight.
Sometimes that is useful.
Keep one copy that does not depend on AI
Once the plan is finished, keep the important information somewhere dependable.
That might mean a document on your phone, printed pages or both.
Include:
- accommodation details;
- confirmed booking references;
- transport times;
- travel-insurance details;
- essential addresses;
- emergency contact information;
- official travel advice you need to remember.
You should not need a working chatbot conversation, perfect mobile signal or access to a particular online account to discover where you are sleeping that night.
AI works best when you remain the traveller
There is no particular virtue in planning every part of a trip manually.
If AI saves half an evening of opening twelve browser tabs, that seems a perfectly reasonable use of technology.
But the useful division is straightforward.
Let AI generate possibilities, organise information, spot gaps and help you compare options.
Let official sources confirm facts.
And let yourself decide what actually sounds enjoyable.
The purpose of better technology should not be to squeeze more into a holiday. It should be to remove some of the tedious planning so that the trip itself suits you better.
Key Takeaways
- Give AI specific information about your preferred pace, budget and interests.
- Use it to generate and compare options rather than make final decisions.
- Ask it to identify rushed days and unnecessary travel between activities.
- Treat prices, schedules and opening hours as provisional until independently verified.
- Always check entry rules and safety information with official sources.
- Do not trust an unfamiliar booking site simply because an AI tool mentioned it.
- Use AI to create more breathing room, not merely a longer itinerary.
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One Small Step
Take one trip you are considering and ask an AI tool:
“What five questions should I answer before building an itinerary for this trip?”
Answer those first. You will probably get a better plan than you would by immediately asking it to schedule every day.
