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Plan a 'Goonies'-themed Pacific Northwest road trip with ChatGPT

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Plan a trip from Portland, Oregon, to Seattle, stopping at Olympic National Park. My main goal is to see filming sites from 'The Goonies,' plus a sample of the natural wonders of Oregon and Washington.

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Before you start, ask me 1–3 short questions about the details below and wait for my answers. Once I've answered, confirm the plan in one line and run the whole task start to finish.

Goal: Plan a realistic road trip around one must-see theme without overstuffing the days.

Questions to ask me first:
- What are your start and end points, dates and number of days?
- What is the one theme or must-see that the trip is built around?
- How many hours a day are you happy to drive, and how active are you?

Inputs (fill in or confirm):
- Route and dates: [START / END / DATES]
- Main goal: [THEME OR MUST-SEES]
- Where I'm staying each night: [LODGING]
- Pace and limits (driving hours, allergies, mobility): [PACE]

Rules:
- Put the main theme first; add other stops only if they fit without rushing it.
- Give each day drive times, a realistic stop count and time for things like picking up a rental car.
- Push back when I add something that won't fit, and tell me what it would replace.
- Flag places that need early arrival, timed entry or a full day.

Checkpoint: Show me the day-by-day plan with drive times before adding any extras I ask for.

If you get stuck: If you don't know current hours, entry rules or crowds, say so and tell me what to check.

Verify before you finish: Check that no day has more driving and stops than fit in daylight, and that the main theme is covered.

Output: A day-by-day itinerary with drive times, stop lists and a short list of things to confirm.

Done when: Every day is doable and the trip's main goal is fully covered.

AI tool

ChatGPT

Outcome

Boston Globe columnist Meredith Goldstein asked ChatGPT to plan a trip from Portland, Oregon, to Seattle with a stop at Olympic National Park, built around filming sites from 'The Goonies.' It produced an itinerary and a list of 'Goonies' sites, but it agreed with every request: Day 1 left little time to pick up a rental car, it added multiple waterfalls, then a Willamette Valley winery, then Thor's Well when Goldstein asked what else not to miss. It also scheduled five other things on the Hoh Rain Forest day. Goldstein stopped revising and turned to people instead: a coworker said to give the Hoh a whole day and pointed out that Sequim is the lavender capital of the country, and Reddit advice to arrive at the Hoh by 7 a.m. meant no wait in line.

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

Known limitations

PartialThe source says it only partly worked, or had a significant problem a person had to deal with.

What went wrong: ChatGPT gave the basics and a 'Goonies' site list but overpacked the days by agreeing with every request; people fixed the plan.

Source

Posted
by Meredith Goldstein (The Boston Globe)
Last checked
Method:
How we verify

https://www.bostonglobe.com/2025/10/30/lifestyle/chatgpt-fumbled-pacific-northwest-trip/

Context: Goldstein used ChatGPT without an account. The useful fixes came from a coworker and Reddit, not from ChatGPT.

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