How to plan a trip with AI, step by step

To plan a trip with AI, give an assistant with web search your destination, dates, budget and interests, then have it build an itinerary that you check point by point on official websites. This 7-step tutorial takes you from the first message to your packed suitcase, including entry rules and translation once you are there.

What you need before you start

• An AI assistant with web search. This is essential. Without web search, the assistant answers from memory, based on knowledge that stops at a knowledge cutoff date. It will not know about closures, roadworks or new timetables.
• Your constraints. Dates or season, number of travellers, rough budget, preferred transport, the pace you like, any specific needs (children, reduced mobility, dietary requirements).
• Twenty minutes. That is enough for a solid first draft, including the main checks.

What you will end up with: a day-by-day plan, a checklist of things to verify, an estimated budget and a packing list, all ready to adjust.

Which assistant should you use?

Most mainstream assistants will do. For travel, what matters is web search with sources, photo uploads and voice for use on the go. Here are the features listed on the providers’ websites:

Assistant	Free	Paid from	Web search	Agent mode	Voice	Images
Perplexity	Limited	$10/mo	Yes	Yes	—	Yes
ChatGPT	Limited	$8/mo	Yes	Yes	Yes	Yes
Gemini	Limited	€4.99/mo	Yes	—	Yes	Yes
Microsoft Copilot	Limited	$9.99/mo	Yes	—	Yes	Yes
Le Chat (Mistral Vibe)	Limited	$5.99/mo	Yes	Yes	Yes	Yes

If you are not sure, our quiz Which AI is right for you? points you in the right direction in a few questions.

Step 1: write a complete brief

The quality of the itinerary depends on how precise your first message is. Put everything in a single request:

“We are a couple in our forties. We are spending 4 days in Lisbon in May, flying from London, with no car. Budget: about £800 for two, excluding flights. We love walking, old neighbourhoods and local food; museums, not so much. Suggest a day-by-day plan at a relaxed pace, with one free evening. Cite your sources.”

This message covers the five things that matter: who, where, when, how much and what you enjoy. The final request for sources nudges the assistant to rely on pages you can open.

Step 2: compare a few options

If you have not picked a destination yet, ask for a comparison table instead:

“Suggest three European destinations for a long weekend in May, reachable by train from London, in a table: travel time, atmosphere, rough budget, pros and cons.”

A table forces the assistant to structure its answer and shows you at a glance what needs checking. Treat travel times and budgets as ballpark figures, never as reliable numbers.

Step 3: build the itinerary day by day

Once you have chosen, refine with small edits rather than starting over:

• “Group the sights by neighbourhood to cut down on travel.”
• “Replace day 3 with a day trip by train.”
• “Add a rainy-day alternative for each day.”
• “Flag any visits that need booking in advance.”

It is a conversation: say what does not work and the assistant adjusts. Keep the final version in a note or a shared document with your travel companions.

Step 4: check times, prices and addresses

This is the step people skip most often. An assistant can produce a hallucination: a museum listed as open on the day it closes, a bus route that no longer runs, a price from two years ago. For anything that costs you time or money, open the source.

Item	Where to check it
Train, flight and bus times	The operator’s website or app
Opening hours and ticket prices	The venue’s official website
Accommodation	The booking site or the property, including cancellation terms
Entry requirements	The destination’s official website and your government’s travel advice
Health and insurance	Your doctor, your insurer or your card provider

Check yourself The assistant says a museum is open every day from 10 am to 6 pm, without citing a source. What do you do?

You open the museum’s official website to check closing days, opening hours on the day of your visit and whether you need to book. Information without a source is a lead, not a fact.

Step 5: go through entry rules and safety

Ask the assistant for a checklist of questions: passport validity, visa or electronic travel authorisation, vaccinations, insurance, driving licence, plug adapter. It is good at making sure you forget nothing, not at giving the final answer.

For the answers, UK travellers can rely on GOV.UK’s foreign travel advice, consulted on 22 October 2026, which covers “entry requirements, safety and security, health risks and legal differences” country by country. US travellers can check the State Department’s travel advisories and enrol in its Smart Traveler Enrollment Program to receive alerts during their trip.

Step 6: budget and packing

Ask for an estimated budget by category, based on the prices you have found: “Here are our bookings and estimates. Make a budget table by category and by day, with a 10% margin for the unexpected.” The assistant does the maths and the layout; the amounts come from you.

Then ask for a packing list that fits your trip: “Packing list for 4 days in Lisbon in May, hand luggage only, lots of walking, one dinner out.” Ask for it as a checklist you can paste into your notes app.

Step 7: use AI once you are there

Once you arrive, the assistants’ mobile apps become handy travel companions:

• Translate a menu or a sign by taking a photo, thanks to multimodal models that can read images.
• Ask for directions or order food in voice mode, having your sentence translated out loud. Our guide to AI voice assistants explains how to turn these modes on.
• Brush up on a few useful phrases before you go: our guide on how to learn a language with AI shows the method.
• Reshuffle a day if it rains or there is a strike, starting from the plan you already have.

Download the essentials before you leave: without a connection, the assistant cannot answer.

Common mistakes to avoid

Asking in one vague sentence. “Plan me a trip to Italy” produces a generic, overloaded plan designed for nobody. Go back to step 1 and spell out your constraints.

Copying the plan without reading it. Assistants tend to cram in too many sights per day and underestimate travel time. Ask explicitly for “a realistic pace, with breaks”, then check distances on a map.

Sharing too much. To build an itinerary, the assistant needs neither your passport number, nor your booking reference, nor your card details. Keep those for official websites and travel operators.

Forgetting to ask for sources. A sourced answer takes one click to check. If the assistant cites nothing, ask again: “Give me the official page link for each timetable.”

What about booking?

Some assistants offer an agent mode: an AI agent that browses websites, compares options and fills in forms for you. According to Perplexity’s help centre, cited in the site’s profile as of 22 October 2026, requests to the browsing agent in its Comet browser are not included in the free plan. Whatever the tool, keep control of the payment and read the cancellation terms. Our guide to AI shopping agents explains how far to let them go.

This tutorial is part of our series on practical uses: find them all in 20 everyday ways to use AI.