QWE AI Academy Most people open ChatGPT, type “Plan a 5-day trip to Rome,” get back a gorgeous itinerary. Day 1: Colosseum, lunch at Trattoria XYZ, Trevi Fountain at sunset. Day 2: Vatican Museums, dinner at Osteria ABC. Looks perfect.
They land in Rome. Trattoria XYZ closed in 2023. Osteria ABC moved. The Colosseum tour? Sold out weeks ago – ChatGPT didn’t check. Now they’re scrambling with tired kids and no backup.
The mistake isn’t using ChatGPT for trip planning. Asking it to plan first, verify later? That’s backward.
Why the Standard Approach Fails
ChatGPT is a language model, not a live booking system. Can’t access paywalled content, private reservation platforms, or login-gated resources. 2025 testing: 90% of AI itineraries had at least one mistake – closed restaurants, wrong hours, unavailable activities.
The tool has no spatial reasoning. Think about it: a “10-minute walk” and a “3-hour train” are identical strings to a language model. Both are sequences of characters. No concept of physical distance, no internal map. I’ve seen itineraries that bounce you across a city four times in one afternoon, or schedule your last museum visit to end when your flight boards.
Plus (as of 2026): ChatGPT performs poorly late in planning – if your itinerary is nearly done, output often becomes less rich, underestimates time at major sites.
The Correct Workflow: Verify, Then Plan
Flip it. Generate components, verify each, then assemble.
Step 1: Start with a Constraints List, Not a Full Itinerary
Don’t ask “a 5-day trip.” Ask what’s actually possible given dates, budget, travel style.
Prompt: "I'm visiting Lisbon March 10-14 with my partner. We like food markets, street art, avoid touristy spots. List 10 activities that fit. Include operating hours and whether advance booking is required."ChatGPT gives you a list. Now verify each – Google the venue, check TripAdvisor for recent reviews, cross-reference hours on official sites. TikTok, Reddit, destination Facebook groups: real-time updates on what’s open, closed, worth skipping. Catches the 90% error rate before you commit.
Step 2: Use Iterative Prompts, Not Mega-Prompts
One tester requested suggestions on-the-go (“I’m in Alfama, what’s a good coffee spot nearby?”) – worked better than planning days upfront. Avoided tourist traps, excess Uber rides.
Build your day in pieces. Verify A. Ask for B near A. Verify B. Continue. Logistics stay tight, bad geography gets caught immediately.
Prompt: "I'm starting my day at Alfama in Lisbon. Suggest 2 coffee spots within a 5-minute walk that locals use, not tourist cafes. Include current Google ratings."After coffee? Ask for the next step. Prevents classic ChatGPT mistake: sending you across town twice in one morning.
Step 3: Give It a Role and Constraints
Community testing: giving ChatGPT a role (‘You are an experienced Lisbon guide’) plus personal constraints (‘we walk slowly’, ‘we read museum texts’) improves results.
Prompt: "You are a local Lisbon guide specializing in off-the-beaten-path experiences for couples in their 30s. We walk at a moderate pace, prefer to avoid crowds, want authentic food over Instagram spots. Starting afternoon in Bairro Alto. Suggest one activity and one dinner spot. Both must be currently operating and not require reservations more than 2 days in advance."Notice the specificity. “Currently operating” forces it (if using Browse mode) to think about recency. “Not require reservations more than 2 days in advance” blocks Michelin spots you can’t get into.
Pro tip: Refining and quality drops? Fewer options, ignores earlier constraints? Start a new chat. Context window sometimes “forgets” early instructions when threads get long. One debugging session burned through my 100 messages/day faster than expected.
The Hidden Pitfalls
Outdated Information Is Systematic
Not random. Real tests found ChatGPT suggesting Ciel de Paris (closed), Brasserie Gendarmenmarkt (closed summer 2024), Pergamon Museum (shut 2023, reopening 2037). Free tier: tight browsing limits. Plus users: outdated data unless you explicitly ask to verify current status.
Double-check everything. Every restaurant. Every museum. Every tour. Official websites, not ChatGPT’s word.
Refining Makes It Worse
One tester narrowed criteria multiple times (more chicken, certain cuisines): ‘each time, the itinerary became worse, with a drastic drop in activities’. Quality tanks during iteration? Start over with a clearer initial prompt.
It Can’t Do Logistics
Doesn’t know train schedules, real-time traffic, security line lengths. Can’t tell you if a campground is full or if a road is closed due to weather. Doesn’t access live calendars or reservation systems. After you have verified components, you build the timeline. Don’t trust time estimates.
When ChatGPT Shines
| Use Case | Why It Works |
|---|---|
| Brainstorming destinations | Give it constraints (budget, climate, travel time), get 10 options fast. Saves hours of Googling “best spring destinations.” |
| Comparing options side-by-side | “Compare Porto vs. Lisbon for a 3-day trip: food and architecture.” Synthesizes faster than opening tabs. |
| Packing lists | “Packing list: Iceland, November, hiking, Northern Lights, minimalist.” Solid output, low error risk. |
| Cultural prep | “Common customs in Japan. Include tipping etiquette, dining manners.” Static knowledge – ChatGPT handles it well. |
Not good at: final decisions or booking details. Users still rely on real-world experience and common sense before committing to flights, hotels, activities.
When NOT to Use ChatGPT
Some scenarios are a bad fit:
- Booking time-sensitive reservations. Can’t check real availability. By the time you verify, slots are gone.
- Traveling somewhere niche or rural.Smaller towns: data is thin or overly promotional – itineraries look like ads for chain hotels instead of genuine recommendations.
- You enjoy the research process.Some travelers love deep research – ChatGPT solves a problem that isn’t a problem. Planning is half the fun? Don’t outsource it.
- You need hyper-local, secret spots.ChatGPT is trained on widely available data – well-ranked pages. Won’t uncover the secret spot no one’s blogged about.
Reality check: Academic research found travelers show reduced trust and satisfaction when ChatGPT narrows options – process feels too subjective and emotional for AI. Use it to expand options, not finalize them.
A Quick Performance Benchmark
Tested the verify-then-plan approach on a 4-day Porto trip. Asked ChatGPT for 15 activity options with hours and booking requirements. Verified each. Five were wrong: three had changed hours post-2023, one closed for renovations, one required a reservation I couldn’t get.
Built a day-by-day plan manually using the 10 verified options. Asked ChatGPT to optimize geography (“Visiting A, B, C, D – what order minimizes backtracking?”). That worked. Final itinerary: zero surprises. Every venue open. No wasted Ubers.
The $20/month Plus subscription (as of 2026) helps – Browse with Bing gives slightly fresher data – but even Plus won’t catch everything. The verify step is non-negotiable.
Your Next Action
Don’t build an itinerary yet. Start here: pick your destination, write one constraint-heavy prompt (dates, budget, style, mobility needs), ask for a list of 10 options with operating details. Verify the list. 8 out of 10 check out? You’ve got a foundation. Half are wrong? You just saved yourself a terrible trip.
Then, once you’ve verified components, ask ChatGPT to sequence them. “I’m visiting these 8 verified spots over 3 days. Suggest a logical order that minimizes travel time.” Use it as a logistics assistant, not a research oracle.
Open ChatGPT. Write your first prompt. Verify before you plan.
Frequently Asked Questions
Can I use the free version of ChatGPT for trip planning, or do I need Plus?
Free tier works for brainstorming and static info (packing lists, cultural tips). Plus ($20/month as of 2026) unlocks Browse with Bing – helps with recency. Still need to verify everything. Planning one big trip? Plus might be worth it for that month. Cancel after.
How do I stop ChatGPT from suggesting tourist traps?
Be explicit: “Avoid major tourist attractions. Suggest spots locals use, not places in top-10 listicles.” Also: “Exclude chain restaurants” and “Prioritize venues with fewer than 500 Google reviews.” One tester had to repeatedly veto chains – ChatGPT tried sneaking in Turtle Bay, Gail’s Bakery, Franco Manca despite a no-chains rule. Be firm.
What’s the best way to verify ChatGPT’s suggestions quickly?
Google the venue name + “closed” or “hours.” Check official website or Google Maps for current status. Then TikTok, Reddit, destination Facebook groups – travelers share real-time updates on closures and whether something is worth visiting. 2 minutes per venue. Remember that Lisbon tester who found three “must-visit” restaurants permanently closed? One had been shuttered since 2020.