DIY trip planning with booking sites, reviews, and A.I. often leads to stress, hidden costs, and missed moments. Common mistakes include chasing cheap deals, overstuffing itineraries, trusting reviews blindly, ignoring “what ifs,” and relying too heavily on A.I. A travel advisor offers expertise, advocacy, and peace of mind so your journey feels free, not frantic.
May 25, 2022
With so many booking sites, blogs, and A.I. tools at our fingertips, it’s tempting to think planning a trip on your own is easy. And don’t get me wrong, I get the appeal. I’ve used these tools myself for inspiration, and platforms like ChatGPT can be a great starting place for brainstorming destination ideas.
But here’s the truth: when it comes to actually booking and managing an entire trip, DIY planning often leaves travelers overwhelmed, stressed, and sometimes out thousands of dollars. Over the years, I’ve seen the same mistakes pop up again and again. Let’s talk about the five biggest mistakes people make when booking travel themselves, and how you can avoid them.
We’ve all seen the flashy “deals” online: $99 airfare or hotel rooms that seem too good to be true. And often… they are. What most people don’t realize is that the cheapest option usually comes with strings attached: hidden fees, rigid cancellation policies, or inconvenient connections that end up costing more in time, money, and stress.
As a travel advisor, I look at the full picture, not just the price tag. Sometimes spending a little more upfront saves you huge on headaches later.
It’s easy to fall into the trap of wanting to “see it all.” You’re going to Italy, so of course you should squeeze in Rome, Florence, Milan, Venice, Cinque Terre, the Amalfi Coast, and maybe even Sicily… right?
The reality is that overstuffed itineraries lead to burnout. Instead of soaking in the beauty of each place, you’re rushing from train to train, barely catching your breath.
Part of my role is helping clients strike the right balance: creating space for adventure, but also for rest, spontaneity, and the kind of unplanned moments that make travel magical, like wandering the streets of Rome and waiting in line with locals for two hours to score a seat at a hole in the wall restaurant that serves the best pizza and tiramisu of your life (trust me, true story).
Reviews can be helpful, but they’re also subjective and sometimes misleading. A five-star review from a backpacker might not mean the same thing to someone looking for luxury comfort. And let’s be honest: some reviews are planted, outdated, or based on unrealistic expectations.
When you work with a travel advisor, you’re not relying on strangers from the internet. You’re tapping into vetted partners, firsthand experience, and a global network of trusted colleagues who know what’s truly worth your time and money.
Here’s one of the biggest gaps I see when people plan trips themselves: no one thinks about what happens when things don’t go according to plan. Flight canceled? Luggage lost? Weather disruption?
If you booked on your own, you’re the one waiting on hold for hours with a call center in another country, often with little leverage to resolve the issue.
But when you book with a travel advisor, you have an advocate. That’s where I step in, rebook, troubleshoot, and make sure you’re cared for so you can keep focusing on the experience, not the chaos.
Tools like ChatGPT are incredible for brainstorming travel ideas, building bucket lists, or learning fun facts about a destination. I even recommend clients use it as a starting point if they’re unsure where to go.
But when it comes to booking the actual trip? That’s where A.I. falls short. It might give you an itinerary that looks great, but is actually very deceptive and unrealistic because it has you traveling to ten different tourist hot spots in a day that are hours apart from each other. A.I. also can’t confirm availability, or troubleshoot disruptions in the event you need assistance on your trip. It doesn’t have access to live booking systems, nor does it know your personal needs, preferences, or travel style the way a human travel advisor does.
In fact, I’ve had clients come to me after trying to plan with A.I. alone, only to realize they felt more confused than confident. So just remember, A.I. is a tool, not a replacement for personalized expertise and support.
Travel should feel like freedom, not stress. And while online tools and A.I. can spark great ideas, they can’t replace the value of having a real person in your corner. Someone who understands your story, anticipates your needs, and takes care of the details so all you have to do is show up and soak in the moments.
Because at the end of the day, the greatest mistake isn’t just booking a bad flight or missing out on an experience. It’s letting stress steal from the joy of the journey. And that’s one mistake I’ll never let my clients make.
