ChatGPT: Road trips & car rental

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.

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.

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.

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.

Plan a dog-friendly 7-day RV trip with short drives using ChatGPT

Planning an RV trip from Tampa with their partner and their dog, a poster asked ChatGPT for a 7-day route with no drive over 4 hours, waterfalls and short hikes, and dog-friendly stops. They also used it to check which state parks allow dogs on trails, how to connect a 30-amp RV to a 50-amp site, campfire cooking steps and campgrounds with cell service. They say it gave a day-by-day route with mileage and drive times, and dinner was saved.

Handle parking, road tolls and EV charging questions on a European road trip with ChatGPT and Grok

On a family road trip through Germany, Austria, Italy, Croatia and Slovenia, a poster used ChatGPT and Grok as an on-the-go assistant: planning village visits, walks and beaches, finding fairly-priced safe parking, choosing local beers and wines, and answering first-time EV road-trip questions such as where to buy national vignettes online, road taxes and trip-time estimates.

Plan a month-long family road trip with kosher meals using ChatGPT and Grok

Planning a month-long road trip for a family of seven, a poster used ChatGPT and Grok to map routes between national parks without backtracking, break long drives into kid-friendly segments, find lodging that fits, research kosher food and the kitchen kit needed for Shabbos, and create packing lists. They note it didn't understand kosher certification symbols and that it's not perfect.

Plan a summer road trip by answering questions one at a time with ChatGPT

In a Tom's Guide road-trip feature, Elton Jones shares an all-in-one prompt (written with ChatGPT's help) that has the chatbot ask about starting point, budget, trip length, travel style, food, music, routes, lodging and companions, then build an itinerary, driving schedule, budget, packing list, food stops, scenic stops and rain plans. It offers prompts only and doesn't report a finished trip.