Get the lay of the land for a trip in half an hour and book a rental the same night with ChatGPT (partial)

Posted

Jul 19, 2025 by Kelsey Vlamis (Business Insider)

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Last checked

Oct 18, 2026

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Method:

How we verify

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

Outcome

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.

Agent

ChatGPT

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: Give me the overview I'd normally get from hours of reading about a destination, so I can choose where to stay.

What I'll share as we go:
- The destination and dates
- What I enjoy (food, drinks, nature, shops, crowds or not)
- What I've already booked, if anything

Rules:
- Summarise what each town or neighbourhood is known for and who it suits.
- Say which popular sights are often called overrated and which are worth the crowds, and the best times to go.
- Give two or three varied sample itineraries.
- Push back on marketing-speak and flag anything that may have closed or changed.
- 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 short destination briefing, a recommended base with reasons, and sample itineraries.

You'll know it worked when: I'm confident choosing where to stay without hours of background reading.

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: Give me the overview I'd normally get from hours of reading about a destination, so I can choose where to stay.

What I'll share as we go:
- The destination and dates
- What I enjoy (food, drinks, nature, shops, crowds or not)
- What I've already booked, if anything

Rules:
- Summarise what each town or neighbourhood is known for and who it suits.
- Say which popular sights are often called overrated and which are worth the crowds, and the best times to go.
- Give two or three varied sample itineraries.
- Push back on marketing-speak and flag anything that may have closed or changed.
- 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.
- Check that every restaurant and attraction you name is still open, with a link.

Output: A short destination briefing, a recommended base with reasons, and sample itineraries.

You'll know it worked when: I'm confident choosing where to stay without hours of background reading.

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.businessinsider.com/travel-chatgpt-use-case-plan-trips-saves-hours-2025-7