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

Posted

Nov 9, 2025 by John Brandon (Tom's Guide)

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Last checked

Oct 17, 2026

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Method:

How we verify

Evidence: Article or interviewA newsletter, journalist or interview account of what happened.

Context: In a comparison test: from a head-to-head chatbot review, not a standalone agent test.

Outcome

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 he followed its plan exactly, calling it a blast.

Agent

DeepSeek, Gemini, ChatGPT, Claude, Copilot

The source didn't share its exact prompt, so we wrote this from what it describes.

Let's work this out together. I'll tell you what I know, you suggest options and ask what you need, and we'll narrow it down step by step. Nothing gets booked, bought or sent until I say so.

Goal: Plan a family road trip with a sensible base, a mileage cap, meals and stops.

What I'll share as we go:
- Start point, destinations and number of days
- Mileage or driving-time limits
- Who's coming (kids' ages)
- Lodging style and budget
- Cooking setup for meals

Rules:
- Pick a base that minimizes moving hotels with kids; explain the choice.
- Add up total miles and keep under my cap.
- Name actual gas and food stops near the route.
- Give a meal plan for each day and a grocery list built from it.
- Check lodging availability and prices on official booking sites.
- If a site asks for a login, a CAPTCHA or payment details, stop and hand control back to me.
- Ask for my OK before you pay, book, send, submit or cancel anything.
- Check facts that can change (prices, opening hours, dates, availability, rules) against the official source, and tell me anything you couldn't verify.

Output: A day-by-day plan with a theme for each day, mileage totals, stops, meals and a grocery list.

You'll know it worked when: the whole route is under my mileage cap and every night has somewhere to stay.

Let's work this out together. I'll tell you what I know, you suggest options and ask what you need, and we'll narrow it down step by step. Nothing gets booked, bought or sent until I say so.

Goal: Plan a family road trip with a sensible base, a mileage cap, meals and stops.

What I'll share as we go:
- Start point, destinations and number of days
- Mileage or driving-time limits
- Who's coming (kids' ages)
- Lodging style and budget
- Cooking setup for meals

Rules:
- Pick a base that minimizes moving hotels with kids; explain the choice.
- Add up total miles and keep under my cap.
- Name actual gas and food stops near the route.
- Give a meal plan for each day and a grocery list built from it.
- Check lodging availability and prices on official booking sites.
- If a site asks for a login, a CAPTCHA or payment details, stop and hand control back to me.
- Ask for my OK before you pay, book, send, submit or cancel anything.
- Check facts that can change (prices, opening hours, dates, availability, rules) against the official source, and tell me anything you couldn't verify.
- Before I book, confirm opening dates and reservation rules for parks and campgrounds on official sites.

Output: A day-by-day plan with a theme for each day, mileage totals, stops, meals and a grocery list.

You'll know it worked when: the whole route is under my mileage cap and every night has somewhere to stay.

Before you finish: re-read my goal and constraints, check your answer against each one, and list anything you assumed or couldn't confirm.

Source

https://www.tomsguide.com/ai/i-made-five-chatbots-plan-my-holiday-it-wasnt-chatgpt-or-gemini-that-gave-me-the-best-response