AI Helped Me Choose My Next Travel Destination

Prologue: The Urge to Escape
It started with that familiar itch — the one that creeps in when your daily routine starts feeling like a looped GIF. Wake up, coffee, work, dinner, Netflix, sleep. Repeat.
I’d been staring at my laptop for hours, not because I was working, but because I was daydreaming. My mind kept drifting to cobblestone streets, the smell of fresh bread from a bakery, the sound of a language I didn’t understand.
I needed a trip. Not just a weekend getaway — a real change of scenery. But here’s the problem: I’m terrible at choosing where to go. Give me a list of options and I’ll spiral into analysis paralysis.
That’s when I thought: Why not let AI decide for me?

The Idea: Letting AI Decide
I’ve used AI for plenty of things — brainstorming blog ideas, editing photos, even helping me learn Photoshop in a weekend. But travel? That felt… personal.
Still, I figured it was worth a shot. I opened ChatGPT and typed:

Within seconds, it gave me a shortlist: Reykjavik, Kyoto, Tbilisi, and Venice.
Venice was an easy no — beautiful, yes, but I’d been there before, and I wanted something new. Reykjavik sounded magical but pricey. Kyoto was tempting, but I wasn’t in the mood for long-haul flights. Tbilisi intrigued me, but I wasn’t ready to commit.

Step 1: The Initial Ask
The first list was a good start, but it was too broad. I realized I needed to be more specific. So I told AI:

Travel dates: late May
Flight time: under 10 hours from my city
Weather: mild, no heatwaves
Political situation: stable
Airport close to the city center
Must-have: a local food scene worth exploring
This time, the list came back as Austin (Texas), Charleston (South Carolina), and Valletta (Malta).
Austin felt too loud for the mood I was in. Charleston sounded charming. Valletta… I barely knew anything about it, but the name alone made me curious.

Step 2: The Thought Experiment
I decided to run a little experiment. I asked AI to simulate what it would be like if I landed in each city tomorrow.
For Charleston, it painted a picture of oak-lined streets, pastel houses, the smell of shrimp and grits, and jazz spilling from a small bar.
For Valletta, it described honey-colored buildings, narrow limestone steps, the sound of church bells, and the taste of warm pastizzi from a street vendor.
I could almost feel the Mediterranean sun on my face.

Step 3: Fact-Checking Offline
AI is great, but I’m not about to book a trip based solely on a poetic description. I cross-checked everything:

Google Flights: Valletta was surprisingly affordable.
Travel blogs: Consistently glowing reviews about its architecture and history.
YouTube vlogs: Gorgeous golden light, walkable streets, and endless sea views.
The more I looked, the more it felt right.

Step 4: The Winner — Valletta, Malta
By Sunday evening, I’d made my choice. Valletta ticked every box:

Compact and walkable
Rich history (Knights of St. John, fortresses, cathedrals)
Mediterranean food and coffee culture
Affordable flights and accommodation
I booked my ticket before I could overthink it.

Why AI Made the Difference
Here’s the thing: I could have found Valletta on my own. But AI made the process faster, less stressful, and — honestly — more fun.
It acted like a travel-savvy friend who knew my preferences, filtered out the noise, and gave me a shortlist I could actually work with.
Instead of spending weeks scrolling through “Top 50 Destinations” lists, I went from idea to booked ticket in two days.

The Human + AI Partnership
What I loved most was how collaborative it felt. AI didn’t tell me where to go — it guided me. I still did the fact-checking, watched the videos, read the reviews. But AI gave me a starting point and a vision.
It also reminded me that technology doesn’t have to replace human decision-making. It can enhance it.

Looking Ahead
As I write this, my trip is a few weeks away. I’ve already asked AI to help me plan my itinerary:

Morning walks along the Grand Harbour
Afternoon exploring St. John’s Co-Cathedral
Evenings in tiny cafes, watching the world go by
I can almost hear the echo of footsteps on those limestone streets.

Final Thoughts
AI didn’t just help me choose a destination — it helped me cut through the noise, focus on what mattered, and make a decision I feel excited about.
And that’s the real magic: not that it “picked” Valletta for me, but that it made the process feel effortless and inspired.