Trip planning & itineraries: 28 real cases

Plan three family days in Paris, with ticket links, using Copilot

Paolo Asnaghi planned three August days in Paris for two adults and an 11-year-old, using only Copilot (with GPT-5). Asnaghi asked what to see from the hotel's area, excluding Disneyland, then asked for links to buy tickets in advance next to each description. Copilot grouped sights to avoid crossing the city, showed approximate prices and suggested a 3-day transit pass instead of single tickets. In about half an hour Asnaghi had a customized guide. The PDF it made wasn't user-friendly, though. During the trip, Copilot helped find places to eat, explained sights from photos and checked the weather for the next day's plans.

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.'

Book a trip, flight, hotel and shuttle with ChatGPT Dots, and keep confirming the same booking (partial)

neom spent two hours trying ChatGPT's Dots agent and grades it B-. Asked to figure out a trip, it did; neom booked the flight and hotel, and Dots noticed the shuttle hadn't been booked and offered to book it with the details they'd discussed. But after neom said yes, it went back to the site, re-checked the details, asked for confirmation, filled in the booking form and then asked again whether to book. It can sign in with passwords, but wouldn't fetch two-factor codes from email even with email access, and its permissions checker rejected broad rules neom wrote, such as proceeding with routine, reversible actions without asking. neom finds it faster to use regular chat.

Get real flight and hotel prices from a Claude Code travel skill, which only guessed price ranges until it was given a browser (partial)

Christopher Johnson built a Claude Code skill in about twenty minutes to act as a travel agent, sorting flights and places to stay for a business trip. Asked for real prices, it gave ranges, such as 'Flights typically run $280 to $420', and none of them was a price they could actually pay. Claude explained that the booking sites load prices with JavaScript after the page renders, which its tools couldn't see, so it had been estimating. With the Claude in Chrome extension installed and the same skill and request, it opened the sites and returned three specific places to stay with current prices and direct links. It was slower and used more of the plan's usage limits. They kept 'Act without asking' off, and Claude never bought anything.

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.

Underpack for a Mount Shasta climb after following Gemini's advice, ending in a rescue

According to the U.S. Forest Service, three novice hikers planned a Mount Shasta climb partly with Google Gemini, which recommended supplies for an 8-hour climb rather than the 16 hours it took and told them to eat simple carbohydrates rather than fats. They reached the summit at 7 p.m., got lost off-route on the way down after their phone battery died, and one hiker injured a knee at about 11,500 feet. Rangers reached them the next morning; the hikers said they 'relied too much on AI rather than our own critical thinking.'

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.

Plan a flexible beach day with an infant in Goa by voice with Gemini

Overwhelmed by pins on Google Maps while travelling with an infant, Android Police's Akshay Bhalla asked Gemini by voice for a flexible day at Mandrem Beach in North Goa: sunset, local food at a beach shack rated 4.2 or higher, maybe water sports, using maps, weather, UV index, traffic and blogs. Gemini suggested a creek in the morning, a local restaurant for lunch, shade during the peak UV hours of 11:30 AM to 3:00 PM, and the beach from 5:30 PM for sunset, then added a café with good Wi-Fi when asked.

Plan a month of family travel and remote work across Europe with Gemini, from route to co-working bookings

Planning a month of travel with kids while working remotely, Nick Thomson gave Gemini the family's profile, preferences and goals. It talked them out of a there-and-back route from London to southern Italy, suggesting three routes starting with a flight to the furthest point; recommended beaches by the kids' ages and swimming ability, off-peak trains, surf schools and teen-friendly activities; flagged when train companies release cheap tickets; and found co-working spaces, compared day rates and drafted booking emails in French and Spanish. Over the month, one recommendation was wrong: a bus to a market that didn't exist.

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 two-week Taiwan and Hong Kong trip with a toddler using Gemini and Ask Maps

A New York Times personal tech columnist used Gemini (with personal data from Gmail) and Google Maps' Ask Maps to plan a 14-day Taiwan and Hong Kong trip with their wife and 20-month-old. The columnist says activity planning took only about 30 minutes; Gemini drafted family-friendly daily plans that accounted for jet lag, to-do and packing lists, and found a cheap data plan. But the packing list left out the columnist's own socks and underwear, and in Hong Kong it suggested restaurants near the previous hotel in Taiwan; Ask Maps handled real-time requests better.

Plan a vegetarian trip around Vietnam with Gemini

Over two weeks in Vietnam, Android Police's Parth Shah used Gemini to check weather by region, which showed they'd need warm clothes for Ba Na Hills and Sa Pa, and to build packing lists, shopping hotspots and a list of pure vegetarian restaurants they saved in Google Keep. On the trip it helped them check snacks for eggs and hidden allergens and explained the history behind temples and old towns.

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.

Plan and book a trip with Grok Bot (7-step prompt set)

A shared sequence of seven prompts for planning a trip with Grok Bot: a travel brief, three priced options, a fare watch, a booking step with a confirm-before-paying check, a paperwork checklist, a day-by-day itinerary and a day-before briefing. The post is a prompt guide; it doesn't show a completed booking or any results.

Book a whole weekend trip in 30 minutes with ChatGPT Work

ChatGPT read the poster's chat with their girlfriend, proposed itinerary options, staged an Airbnb, rental car, fishing gear and dinner reservations through browser use, then made a shareable trip page after the poster booked.

Plan a solo summer vacation with Gemini (forgot it was a solo trip)

XDA's Mahnoor Faisal let Claude, ChatGPT and Gemini plan a real summer vacation they were taking alone. They say Gemini kept forgetting basics, repeatedly defaulting to group and couple-oriented ideas like a romantic candlelight dinner, and tended to agree their plan was great when it needed work.

Build a work-trip itinerary from booking emails with Claude

The day before a work trip, Claude read the poster's booking emails and organized a polished itinerary that the poster says would have taken a few hours by hand.

Plan a vacation with flight, hotel and busy-week checks in Gemini

A Hacker News commenter says they've been using Gemini to plan a vacation and finds it surprisingly useful: it can look up flights from Google Flights and hotels from Maps, and knows about busy weeks at the destination. They add that you have to hope it isn't hallucinating, which they see as safer for trips than for healthcare.

Plan a family Disneyland trip with Claude Code and Skills

The poster planned a family Disneyland trip using Claude Code as the agent, Claude Skills for research, planning, tracking and journaling, and a simple companion web app for itineraries and maps.

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.