Planning six days of cycling around Lake Champlain, a rider gave the same prompt to several chatbots. Perplexity was the only one to produce a real loop around the lake, even reminding them to pack a passport for the Canadian leg, but its day lengths were uneven; the others misstated distances and ChatGPT suggested a hotel that didn't exist. In the end the rider rebuilt the route in RideWithGPS.
Plan a [NUMBER]-day cycling tour around [ROUTE OR AREA], starting and ending in [TOWN]. Keep each day between [MIN] and [MAX] miles or km, prefer bike paths to roads, stay in [HOTELS / B&BS / CAMPSITES] and suggest a lunch stop each day. Show each day's start, end and distance, and link the sources you used so I can check them.
Replace the [PLACEHOLDERS] with your own details before you send it.
How to try it
- Use the AI plan only as a first draft of towns and overnight stops.
- Map every day in a route planner such as RideWithGPS or Komoot to check real distances and climbing.
- Confirm each hotel and lunch stop actually exists and is open before you book.
More travel use cases
Plan an Interrail route with a baby in tow using ChatGPT
A solo mum who spent 25 days travelling by rail from London to Pisa with her six-month-old used ChatGPT to plan the route, asking specifically for pram-accessible trains and quieter departures away from rush hour. It was mostly helpful, but a few times it suggested trains that didn't exist where there were only buses.
I'm travelling by train from [START] to [END] over [NUMBER] days with a [AGE] baby and a pram, using [RAIL PASS]. Suggest a rough route with stops, keeping each train journey under [HOURS] hours, favouring step-free or pram-friendly stations and quieter departure times. For each leg, name the operator so I can check the timetable myself, and flag where I might need a seat reservation.
Get two AI tools to plan your trip, then combine the best bits
A couple planning Tunisia had ChatGPT and Claude each design a day in the same three cities, then built their own plan from both. ChatGPT's ambitious desert day was too much, but Claude's food tour and two historical detours became highlights.
We're visiting [CITIES] in [COUNTRY] from [DATES]. Design one full day in each city for two adults who enjoy [INTERESTS]. Be realistic about travel times between places and flag anything weather-dependent. Explain why you chose each stop.
Write a detailed prompt to get a travel plan that feels like yours
Planning Key West, a Kiplinger writer found a simple 'two-day itinerary' prompt gave generic tourist picks. Adding details such as 'focus on water activities, include a ghost tour, build in hotel breaks, no breakfast' produced plans that felt like hers, though everything still needed checking.
Create a [NUMBER]-day itinerary for [DESTINATION]. The atmosphere I want: [E.G. RELAXED, OUTDOORSY]. Must include: [E.G. A GHOST TOUR]. Focus on: [E.G. WATER ACTIVITIES]. Build in: [E.G. AN AFTERNOON BREAK AT THE HOTEL]. Skip: [E.G. BREAKFAST PLANS, BUSY NIGHTLIFE]. Avoid the obvious top-ten list where you can and tell me why each pick suits me.
Reference: Jemal.co