We’ve all seen the headlines. CNN recently sat down with Wall Street Journal travel columnist Dawn Gilbertson to put AI to the ultimate test: Can a chatbot actually plan a vacation?
The short answer? It’s a hot mess.

While AI is great for writing a grocery list or a generic email to your HOA, it’s proving to be a pretty reckless travel advisor. The news report highlighted the glitches, the outdated info, and the lack of “real world” logic.
As the face of Jennie B Travels, I watched that segment and couldn’t help but cringe. Here’s why letting an algorithm handle your hard-earned PTO is a gamble you don’t need to take – and why a human advocate is the ultimate travel flex.
1. AI Has No “Boots on the Ground”
An AI can tell you a hotel in Tulum has five stars. It can’t tell you that there’s a massive construction project next door starting at 6:00 AM, or that the “beachfront” view is actually blocked by a souvenir shack.
At Jennie B Travels, I specialize in the Mexican Caribbean, The Caribbeans, Australia, and many parts of Europe. These aren’t just pins on a map for me. I’ve either walked these streets myself, sent clients there recently, or am knee-deep in advanced education for these regions. I have boots-on-the-ground contacts and professional relationships with suppliers. When I book you, it’s based on a handshake and a history – not a line of code.
2. The “Healthcare Grade” Attention to Detail
You want an orderly timeline? You’ve come to the right place. My 30+ years in healthcare have baked a certain level of precision into my DNA. In a hospital, details aren’t optional – they’re everything.
I bring that same “client advocate” energy to your travel plans. Whether you’re looking for a high-end land tour through Italy or a luxury cruise through the Great Barrier Reef, I’m the one double-checking the logistics so you don’t have to. I handle the “what-ifs” before they become “oh-nos.”

3. Bougie Taste, Real-World Protection
I’ll be honest: I have “bougie-ish” taste. I like the finer things, the orderly itineraries, and the elevated experiences. But I’m also your protector. If a flight gets canceled or a resort isn’t living up to the promise, an AI will give you a scripted, emotionless apology – a digital shrug that does nothing to get you to your destination. I give you a solution. I’m also a certified Wedding & Event Planner. If you’re planning a destination wedding in the Caribbean or a milestone event in Europe, you need a conductor for that orchestra – not a chatbot that might hallucinate a venue that closed in 2023.
The Bottom Line
Travel is an investment of your time, your money, and your sanity. Why leave that to an algorithm that doesn’t know the difference between a “central” hotel and a “middle of nowhere” nightmare?
Whether you want to sail the blue waters or explore the historic heart of Europe, let’s do it right. I’ll handle the stress, the suppliers, and the tiny details. You just worry about what to pack.
Ready to ditch the chatbot and level up your travel?
Let’s get your next adventure on the books – exactly the way you pictured it.

View comments
+ Leave a comment