AI for travel planning: 102 real cases with prompts

Plan a six-day Oregon trip day by day with ChatGPT and Google Maps

The poster booked flights and Airbnbs, then for each day gave ChatGPT the start and end Airbnb, the kind of places they like and how much walking they were up for, and asked what to see along the route. They checked every suggestion on Google Maps, asked for hidden spots, then asked whether each day was feasible and what they'd missed, which turned up a redwood trail. Planning took about four hours; the poster says the plan worked almost perfectly without feeling rushed.

Win a Lufthansa refund for a cancelled trip over months of ChatGPT-written emails

After a Lisbon–Frankfurt–Miami flight was delayed, boarded and then cancelled, the poster gave up the trip and flew elsewhere. Lufthansa tried to charge for the Lisbon–Frankfurt leg and offered only 'the difference'. The poster fought it entirely by email using ChatGPT, and after months and a long chain of emails got the refund. They still lost money, days and the trip with their mother.

Draft a 13-day cross-country motorcycle route with Grok and ChatGPT, then catch a badly wrong route map

Planning a 13-day cross-country motorcycle ride for a year ahead, the poster asked Grok and ChatGPT for an initial route and itinerary. Grok's itinerary was 'a little wonky'; ChatGPT's schedule and route looked great. But when asked to draw a map of the route it had described, ChatGPT produced one that the poster says gets worse the more you look at it, making them question whether the itinerary itself was accurate.

Avoid the wrong travel insurance for a student abroad with ChatGPT

The poster's son, a Canadian studying in the U.S., was travelling overseas, and the poster almost bought travel insurance out of habit. ChatGPT pointed out the key issue: for this cover, residency mattered more than citizenship. They compared options and chose IMG Patriot International.

Find the best Starbucks detour on a family drive with Grok in a Tesla

About 90 minutes from their destination, with the family wanting hot chocolate and coffee, Shiva Arunachalam asked the Grok integration in their Model Y to find the best Starbucks on the way, with the shortest detour, the right direction of travel and timing so drinks would be ready, and to adjust the route. Arunachalam says it picked the right store and re-routed cleanly; they placed the mobile order by hand in the Starbucks app, and the drinks were ready on arrival.

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.

Find off-the-radar stops along a 5,600 km road trip with ChatGPT o3

Planning a week-long road trip from Chicago to San Francisco via Alabama, Mississippi and Louisiana, the poster gave ChatGPT o3 a rough route, the things they wanted to see and questions in XML format, then refined the daily plans and switched part of the route. Asking 'is there anything to see between [x] and [y]' surfaced places they'd never heard of, including the Space and Rocket Center in Huntsville, Dauphin Island and its car ferry, and Saguaro and Guadalupe Mountains national parks, which they count among the best parts of the trip.

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 parent-and-daughter road trip from the Bay Area to Texas, with a halfway stop and hotels, using Grok

A parent asked Grok on an iPhone to plan a road trip with their daughter from the Bay Area to Tesla Giga Texas, with a stop halfway and hotel recommendations; then booked the hotels and added them to the calendar. On the road they asked Grok for food and rest stops when needed. The poster says LA traffic added 7 hours to one day, and they missed the factory tour because tickets sold out.

Get a $1,373.97 refund for a changed flight via a bank chargeback, on Grok Bot's advice

After an airline schedule change, a traveller asked for a full refund on two China Eastern tickets booked through an online travel agency; the agency confirmed it in writing on Sep 8 but then stalled through 8 complaint emails. Grok Bot advised them to stop waiting and dispute the charge with their bank. On Oct 11 the bank ruled in their favour and they got the full $1,373.97 back.

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.

Get back to the US without a passport book after being denied boarding, with Grok's plan

Denied a flight back to the US because they only had a passport card, not the book, a traveller asked Grok what to do. The traveller says it suggested taking an Uber to the border, linked them with a private car from the border to the airport, said which security checkpoint to use and calculated the travel time; they missed the first flight but caught the layover after a 4-hour drive.

Get a refund from Airbnb for a stay with no hot water using ChatGPT agent

After an Airbnb stay with no hot water and a host-required third-party app that didn't work, a guest explained the problem to ChatGPT by voice and uploaded a video. Instead of drafting an email, ChatGPT opened its cloud browser, had the guest log in to Airbnb, found the stay, opened a support ticket, asked for a human, made the case and uploaded screenshots from the video; the guest only stepped in to approve messages. A representative called and the guest got $250 back.

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.

Use Gemini each morning on holiday to plan the day's route, sights and meals with Google Maps

On vacation, Stefan Heil asked Gemini every morning for a route for the day: what to see, where to eat and roughly when to be where. Through its Google Maps integration it surfaced places they wouldn't have found, sanity-checked their own plans, and found a restaurant and somewhere to unwind at the end of long days. Heil notes they didn't compare it with other AI tools.

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.

Read signs, menus and supermarket labels abroad with Gemini Live

On a trip to Barcelona, Android Police's Rajesh Pandey pointed Gemini Live's camera at Spanish signs and asked what they meant, had it find vegetarian lasagna and other vegetarian ready meals on a supermarket shelf, and used it to understand local café menus instead of ordering the one dish they recognized. They still used Google Translate's Live Conversation for talking with locals and hospital staff.

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.

Ask ChatGPT whether a Schengen visa biometrics waiver applies, and miss the renewed-passport catch

A client applying for an Austrian Schengen visa asked ChatGPT whether biometrics were mandatory. It said they can be waived if you've had a Schengen visa in the last five years, allowing a third party to submit. Visa professional Chandan Pandey noticed the client's previous visa was in an old passport, and the waiver requires it to be in the current one. Pandey refused to submit it on the client's behalf; the client went for biometrics in person and confirmed the rule. Pandey says relying on ChatGPT's answer would have meant a rejected application.

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.

Win an airline's reimbursement appeal for a cancellation hotel and meals with Grok's step-by-step help

After a crew time-out cancelled their Miami flight, Chris Bernasconi was told by a gate agent that passengers were entitled to a hotel, transport and a meal, and saved every receipt and the airline's email. Delta declined the reimbursement claim. Bernasconi asked Grok, which spelled out what to do, how to frame the appeal and what to upload, and offered further steps if it failed. Within an hour of appealing, Delta said payment was on the way.

Get a full refund after a flight returned to its origin, using rules Gemini found

After their diverted flight returned to the origin airport in Delhi, a traveller used Gemini as a crisis consultant: they asked for the specific DGCA rules for a full refund instead of a credit shell, compared night train and bus reliability in fog, and got the exact Metro route to the interstate bus station. They say they secured a refund using the clauses Gemini gave them and were on a sleeper bus within an hour.

Plan a 4-day family road trip to South Dakota with five chatbots and use the best plan

A Tom's Guide writer asked five chatbots to plan a four-day family trip from near Minneapolis to the Black Hills and Badlands, with gas and food stops, meals, lodging and under 1,400 miles in a borrowed minivan. Gemini was best at routing; ChatGPT did worst, with a broken map link and a needless night in the Badlands; Copilot was minimal; Claude was good apart from the route. DeepSeek won by basing the family in Custer State Park and planning every meal, and they followed its plan exactly, calling it a blast.