AI vs. Travel Advisor: What AI Can (and Can't) Do When Planning Your Vacation
AI has changed the way we research travel, and as a travel advisor, I'm actually pretty excited about that.
Yes, you read that correctly! I use AI in my own business. I think tools like ChatGPT, Claude and Gemini can be incredibly helpful when you're dreaming about a trip, researching destinations, comparing ideas, or trying to figure out what might be possible.
Ask AI for 15 anniversary trip ideas, and you'll probably have a pretty fun evening ahead of you, ask it whether you should spend a week in Portugal or Italy, and it can give you plenty to think about. Ask it to build you a 10-day itinerary through Italy, and within seconds you'll have hotels, restaurants, attractions, train recommendations, and a day-by-day plan.
So if AI can do all of that, do you still need a travel advisor?
Maybe. Maybe not.
Because the real question isn't whether AI can create an itinerary, it absolutely can.
The better question is: Can AI design the right trip for you?
And that's where things get a little more complicated.
What AI Is Actually Really Good at When Planning Travel
Let's give the robots some credit. AI can be an excellent research and brainstorming tool.
If you have absolutely no idea where you want to go, it can help you narrow down destinations based on your interests. If you're considering several countries, it can give you an overview of the differences between them. It can help you create packing lists, explain different neighborhoods, brainstorm activities, learn about a destination's history, and give you a basic understanding of how an itinerary might fit together.
For busy travelers who don't have six hours to fall down a Google rabbit hole every time they have a travel question, that's incredibly useful.
But there's an important distinction between travel research and travel planning.
Let's Look at a Real Trip
I'm just finished planning an Italy trip for a couple celebrating their 30th wedding anniversary.
They're traveling to Rome, Florence, and Venice and told me that food is a huge part of why they're excited about Italy.
They love history and absolutely want to experience some of Italy's iconic sights, but they don't want to spend nine days racing from one attraction to another, they're much more interested in a combination of important historical sites, incredible food, smaller local experiences, and enough unstructured time to actually enjoy being in Italy together, and it's exactly the kind of request AI should be able to handle well.
So imagine giving it this prompt: "Plan a 9-day anniversary trip to Rome, Florence, and Venice for a couple who loves food, wine, history, and culture."
The resulting itinerary would probably look pretty good.
What an AI-Generated Italy Itinerary Gets Right
A typical itinerary might recommend three nights in Rome, three nights in Florence, and a few nights in Venice.
In Rome, you'd probably see the Colosseum, Roman Forum, Vatican Museums, Trevi Fountain, and Spanish Steps, Florence would include the Uffizi Gallery, Accademia, Duomo, Ponte Vecchio, and perhaps a day trip into Tuscany, and then you'd finish in Venice with St. Mark's Basilica, Doge's Palace, a gondola ride, and a day visiting Murano and Burano.
It would recommend centrally located hotels like Hilton properties, popular restaurants, perhaps a food tour, and high-speed trains between the cities.
And I want to emphasize that this isn't necessarily a bad trip.
Most of those recommendations make sense!
The problem is that we still haven't really planned a trip for these two people. We've planned a trip for two hypothetical tourists going to Italy.
The Questions an Algorithm Doesn't Necessarily Know to Ask
When a client tells me, "We love food," that's the beginning of the conversation, not the end.
What does loving food mean to you?
Would you rather have a Michelin-starred tasting menu or spend three hours eating pasta and drinking wine with a local?
Would you enjoy visiting a market?
Taking a cooking class?
Going into the Tuscan countryside?
Trying Florence's famous steak?
Do you want reservations every night, or would that make your vacation feel overscheduled?
The same thing happens when someone tells me they "love history." That doesn't automatically mean I should book every museum available.
Maybe you're fascinated by Ancient Rome but couldn't care less about Renaissance paintings, maybe seeing Michelangelo's David has been on your bucket list for 20 years, but spending half a day in the Uffizi sounds exhausting.
Those distinctions completely change an itinerary, and they're exactly why my initial process focuses so heavily on how my clients actually want to travel, not simply where they want to go.
More Isn't Always a Better Vacation
This is one of the biggest differences I see between a generic itinerary and one I would actually recommend.
AI is very good at finding things to do….Sometimes it's almost too good 😂
You can very quickly end up with an itinerary that has you touring the Vatican in the morning, crossing Rome for lunch, visiting another attraction in the afternoon, changing for dinner, and waking up the next morning to do it all over again.
Technically possible? Sure. Would I recommend doing that for nine consecutive days on your 30th anniversary? Probably not.
Your vacation doesn't need to be an efficiency competition, and sometimes the best thing I can put on an itinerary is nothing. An afternoon without reservations, a leisurely lunch, enough time after a tour to wander instead of immediately heading to the next thing, the ability to see a wine bar you like and actually stop instead of saying, "We can't—we have tickets at 3:15.”…..
That's not wasted vacation time. That's literally the vacation.
Logistics Matter More Than They Look Like They Do
This is another place where a beautiful itinerary on a screen and an actual trip can diverge very quickly.
"Take the high-speed train from Rome to Florence" sounds simple, and generally speaking, it is.
But which departure makes sense with your hotel checkout time? How early should you arrive? What happens with your luggage in either city? How are you getting to the station? How are you getting from the station to your next hotel? Does that arrival time interfere with that evening food tour you really want to go on?
Multiply those questions across three cities, several hotels, airport transfers, tours, restaurant reservations, timed-entry tickets, and transportation, and suddenly there are dozens of tiny decisions connecting your trip together.
Individually, none of them is particularly dramatic, but collectively, they're the difference between a trip that feels effortless and one where you're constantly figuring out what happens next.
What I Planned Instead
For this particular anniversary trip, I kept the iconic experiences that actually mattered to my clients and built the rest of the itinerary around how they wanted to experience Italy.
In Rome, that includes an early-access Vatican experience so they can see something important to them without spending their entire day battling peak crowds.
In Florence, they'll see David and the Duomo—but their experience isn't exclusively about museums. There's room for Florence's wine windows, incredible food, and experiences that connect them to Tuscany through what they actually love.
I've curated food-driven experiences for them, including an evening centered around Florentine steak and Tuscan wine. They'll also have a private cooking experience on their last night in Venice, rather than simply another sightseeing tour.
Speaking of Venice…. a generic first-time itinerary frequently sends travelers to Murano and Burano for the day, but instead of automatically checking that box, I included an optional Murano experience that combines a walking tour with a hands-on glass lampwork workshop.
Now they're not simply going to Murano, instead they're engaging with one of the traditions that makes Murano interesting in the first place.
Transportation is part of the design, too. Private transfers are used where they make sense, trains connect the major cities, and their Venice transportation includes the kind of arrival and departure logistics that make navigating a city built on water significantly easier.
Most importantly, there's breathing room!!
They're going to Italy to celebrate 30 years together, and I want them to remember Italy, not their itinerary spreadsheet.
So, Should You Use AI to Plan Your Vacation?
Absolutely go for it.
Use ChatGPT, Google, save 700 Instagram Reels and send each other TikToks at midnight.
Create the world's most chaotic shared Notes app filled with restaurants, hotels, beaches, museums, and one completely unexplained link one of you added six months ago.
I love all of that.
Travel planning should start with getting excited about where you're going.
But when you're ready to turn all those ideas into an actual trip, that's where a good travel advisor becomes valuable.
AI is fantastic at answering, "What could we do?" while my job is helping you answer, "What should WE do?"
And then I take it one step further by helping make sure all of those pieces actually work together.
You Don't Hire a Travel Advisor Because You Can't Plan Your Own Vacation
This is especially important for the clients I work with! The people who love working with us here at Gilded Getaways are smart, capable people! You could spend dozens of hours researching hotels, comparing neighborhoods, reading reviews, figuring out transportation, vetting tours, making reservations, and building your own itineraries.
The question is whether you want to.
When you already have a demanding career and limited time away from it, planning a complicated international vacation can very quickly become another project sitting on your to-do list, and your PTO is too valuable for your vacation to become another job.
So use the tools, bring me the Pinterest board, the saved Instagram posts., the spreadsheet, and even the AI-generated itinerary.
We'll take the good ideas, ditch the ones that don't make sense, and turn all of that inspiration into a trip that was actually designed around the two people taking it.
Ready to spend less time planning your vacation and more time looking forward to it?
