🧠 How to Plan a Trip with AI (And What Still Needs a Human Touch)

July 7, 2025

🧠 How to Plan a Trip with AI (And What Still Needs a Human Touch)

Let’s be honest: planning a trip can be a lot. Scrolling endless blog posts, clicking between maps, finding the right Airbnb, building a daily itinerary, and trying to stick to a budget… it’s enough to make you need a vacation from your vacation planning.

So when AI tools like ChatGPT and Gemini promised faster, smarter trip planning, we thought: let’s try it.

Spoiler: It’s helpful — but it’s not magic.

Here’s what happened when we used AI to plan a real trip, where it fell short, and how we’ve found the perfect balance of AI + human expertise using our go-to trip planning system.

✨ First, What Can AI Actually Do for Travel Planning?

AI is great at:

Giving you a quick list of popular things to do in a destination
Generating a rough sample itinerary
Offering restaurant or hike suggestions based on interests
Sorting through general travel advice across the internet in seconds

Sounds dreamy, right?

It is — up to a point.

🧪 Our Real Test: Could AI Help Us Find the Perfect Airbnb?

We decided to use ChatGPT to help us find the perfect dog-friendly stay in Colorado for a large group with the option for multiple places to stay on the same property to some capacity

We prompted it with:

A unique Stay in Colorado
Separate houses/buildings/entrances
Large enough for a group of 12
Dog-Friendly

“Find a dog-friendly Airbnb in the Finger Lakes region with a fenced yard, close to wineries, under $250/night.”

It gave us:

A decent list of towns
Suggestions like “search on Airbnb using these filters”
A few outdated or vague listings that didn’t really exist anymore

We spent more time trying to fact-check its suggestions than if we’d just searched the way we always do — using filters and keywords like a boss.

Lesson learned: AI is great at brainstorming… but not at booking. It doesn’t know real-time availability, accurate pricing, or which listing has that perfect fire pit view.

💻 Why We Still Rely on Our Own Trip Planner

After wasting 2 hours fact-checking AI’s listings, we opened up google and VRBO/Airbnb for ourselves and got more options doing our tried and true method of searching.

Why? Because it’s how we actually plan trips in conjunction with our Automated Travel Planning Spreadsheet:

Filter Airbnb listings manually using trusted keywords + filters; King Bed is a game-changer of a filter
Paste links into the “Lodging” tab with price/night, pet fees, cancellation policies
Compare listings side by side, by what matters most to us (dog-friendly, walkable, has a view, etc.)
Add final pick straight into our itinerary view with check-in/out times built in

Sometimes a spreadsheet is smarter than AI.

🧠 But AI Can Still Be a Great Starting Point — Here’s How We Use It

Here are our favorite AI prompts to kick off trip planning (and yes — these are great to pair with our spreadsheet planner 👇):

💬 Prompts to Try with AI for Trip Planning

🔎 Destination Brainstorming

“Give me 5 underrated weekend road trip destinations within 4 hours of [your location], ideal for nature lovers and dog-friendly stays.”

🗺️ Rough Itinerary Planning

“Create a 3-day itinerary for [destination] that includes scenic hikes, casual dining, and one local food market.”

🧺 Activity Ideas

“What are some relaxing, off-the-beaten-path things to do near [city] that aren’t tourist traps?”

🐾 Dog-Friendly Picks

“What are 5 dog-friendly wineries or breweries near [town] with outdoor patios?”

🛏️ Airbnb Filtering Help

“What Airbnb filters should I use to find a cabin with a hot tub, privacy, and dog-friendly amenities in [region]?”

🧩 The Sweet Spot: AI + A Smart System

AI can help you get ideas — but turning those ideas into a real trip? That still takes you. And that’s where our automated trip planning spreadsheet comes in.

✨ Built to help you:

Organize dates, budget, activities, and lodging
Visualize your trip day-by-day
Make sure nothing falls through the cracks
And actually enjoy the trip you worked so hard to plan

🔗 Ready to Try It?

We use this exact planner for every trip — whether we’re road-tripping with our dogs or flying to a new city for a long weekend.

Grab your copy here → https://www.wanderawaits.com/products/automated-travel-planning-spreadsheet

And yes, it works beautifully alongside AI.

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