ChatGPT: Trip planning & itineraries

Compare Disney World trip budgets from three AIs with ChatGPT, Gemini and Perplexity

Amanda Caswell gave ChatGPT, Gemini and Perplexity the same prompt: plan a five-day Walt Disney World trip for a family of five flying from Philadelphia, from March 30 to April 3, 2027. ChatGPT came in cheapest, suggesting about $8,500, but its hotel estimate was far too optimistic for those dates. Gemini estimated $10,050 to $13,350 after noticing the dates fall just before Easter Sunday 2027, in a busy spring-break period, and that kids 10 and older pay adult ticket prices. Perplexity's full estimate reached $10,545 to $13,955, more than $5,000 above ChatGPT's figure, and Caswell liked its itinerary best. Caswell judged that Gemini wins on budgeting. When shown the other two estimates, ChatGPT revised its target to about $10,000, with $11,000 available.

Plan a five-country family trip with Gemini, despite some wrong tips (partial)

Manish Kurse planned a family trip through France, Germany, Luxembourg, Belgium and the Netherlands with little kids and several families, testing Gemini and ChatGPT along the way. A detailed prompt in Gemini Canvas, covering needs like vegetarian food and kids in strollers, produced a day-by-day itinerary that saved hours and was updated as plans changed. On the road, the AI helped with a lost parking ticket at an Amsterdam P+R, Brussels metro tickets and questions at the Louvre. But a highly recommended Paris creperie was closed, a pizza tip 'didn't sell pizza', and a chairlift in Cochem was shut. Google Maps mostly had it right; 'even Gemini gave the wrong answers.'

Plan a sunset hike from a ChatGPT itinerary and get stuck at the summit after the last ropeway had gone (failure)

Dana Yao and their spouse used ChatGPT to plan a romantic hike up Mount Misen on Japan's Itsukushima island. They set off at 15:00 to reach the summit for sunset, exactly as ChatGPT had told them. ChatGPT said the last ropeway down was at 17:30, but when they got to the station to descend, the ropeway had already closed, and they were stuck at the top of the mountain.

Plan a romantic, off-the-beaten-path Italy trip when you're too burned out to plan with ChatGPT

Burned out by work and a London heatwave, Santiago Barraza Lopez and their partner handed the planning to ChatGPT with one prompt and three rules: affordable, romantic, away from the tourist crowds. Its picks, all tied to a cheap flight into Salerno, were Salerno's old town, the fishing village of Cetara and Atrani in the shadow of Amalfi. Barraza Lopez says letting go of the planning brought calm and connection, and they came home feeling recalibrated.

Get the lay of the land for a trip in half an hour and book a rental the same night with ChatGPT (partial)

Business Insider's Kelsey Vlamis usually spends hours reading about a destination before booking. For a Door County, Wisconsin trip, Vlamis asked ChatGPT which attractions people call overrated and which are worth the crowds, for timing tips, varied sample itineraries and which town suits someone who likes good food, nature, vintage shops and fewer crowds. In about half an hour Vlamis felt confident enough to book a waterside rental that same night. ChatGPT also recommended at least two restaurants that had closed years earlier.

Plan a Hong Kong trip with Gemini, Grok and ChatGPT (some addresses were made up)

A traveller planned a Hong Kong trip mainly with Gemini, using Grok and ChatGPT as extras, to organise locations, build itineraries, make packing lists and turn store addresses into Google Maps links. The traveller says routes were logical and personalised, but the AIs sometimes produced convincing addresses that didn't exist, and got names, opening hours or whether shops were still open wrong. Next time they'd verify every important detail on maps and official sites.

Build a calm, step-by-step Osaka trip guide for a neurodivergent traveller with ChatGPT

A traveller living with depression says ChatGPT helped them build a personal Osaka travel project: two books designed for them as a neurodivergent traveller, the second a field guide they planned to test in Osaka that September. They say it made the trip feel possible.

Plan a Tunisia trip with ChatGPT vs Claude, then travel the combined itinerary

A writer and their partner had ChatGPT and Claude each plan one day in Tunis, Tozeur and Hammamet, then built their trip from both. ChatGPT's plan was ambitious and cinematic; its Tozeur day 'nearly flattened' them with a far longer drive than implied, and a sandstorm blocked the road to the film sets. Claude's was slower and added two stops they loved, the Great Mosque of Kairouan and El Jem amphitheatre. They say ChatGPT delivered better memories and Claude more comfort and culture.

Make a personalized vacation packing checklist with a shared ChatGPT prompt

TechRadar's John-Anthony Disotto shares a long 'travel assistant' prompt (originally posted on Reddit) that asks for your age, destination and trip details, then builds a categorized packing checklist with clothing, tech, toiletries, luggage type and one commonly forgotten item. Trying it for their own trip, they say ChatGPT broke down their wardrobe into specific business-casual outfits, and that results are only as good as the details you give it.

Pick a holiday destination for three friends from their questionnaires with ChatGPT and Gemini Deep Research

For an AI-planned trip with two colleagues, TechRadar's Josephine Watson sent the same Deep Research prompt and three completed preference questionnaires to ChatGPT and Gemini: four days, one base, about $2,000 each, scenic and filming-friendly. Gemini returned five well-known picks such as Lagos and Mallorca in under five minutes. ChatGPT asked follow-up questions first, then ran 110 searches across 34 sources in 16 minutes and suggested Santorini, Madeira, the Bay of Kotor, Cappadocia and Essaouira. ChatGPT came out on top in their head-to-head.

Compare 7-day Bali itineraries from ChatGPT and Grok

An X user asked both Grok and ChatGPT for a 7-day solo travel itinerary to Bali and says ChatGPT did a better job, with tables and accurate breakdowns of the expenses the poster expected.