IS EVERYONE TAKING THE SAME VACATION?
Updated: Oct 2
BY AMY PIPHER
It’s never been easier to see how someone else spent their vacation.
Open Instagram or TikTok and you can find the hotel they stayed in, the restaurant they booked, the beach they visited, the tour they took, where they bought their cute new bag, and probably the exact spot where they stood to take the photo. Save enough of those posts and, before long, you have the beginnings of an itinerary.
And increasingly, that really is how we’re planning. According to Deloitte’s 2026 Travel Industry Outlook, more than half of Gen Z and millennial travelers use social platforms in their trip planning. Nearly a quarter of travelers were also using generative AI for trip planning by late 2025—three times as many as in 2022.
Skift Research’s 2026 traveler research points to the same shift: the way we discover and plan trips is increasingly spread across search, social media, and AI rather than following one clear path.
There’s nothing inherently wrong with that. These tools can introduce us to places and experiences we might never have discovered on our own.
But before turning someone else’s vacation into your own, I think there’s a question worth asking: What about it actually appeals to you?
INSPIRATION IS A STARTING POINT, NOT AN ITINERARY
Maybe you saw a beautiful hotel on Instagram and immediately saved it for a future trip.
Why?
Was it that particular hotel? Or was it the quiet terrace, the artful interior, the view, or the feeling of being somewhere removed from everything else?
Maybe you watched someone spend a packed day moving from a restaurant to a museum to a market to a rooftop bar and thought, I want to do that.
But do you actually enjoy traveling that way?
The distinction matters because social media is very good at showing us what an experience looks like. AI is very good at generating possibilities. Search is very good at giving us more information.
But none of those things can help us decide whether an experience fits the way we actually want to spend our time.
That access can be incredibly useful. But the more inspiration we have, the more important it becomes to understand what we're responding to in the first place.
Before you copy the itinerary, ask yourself why you want to make it yours.
A GOOD RECOMMENDATION ISN'T ALWAYS THE RIGHT RECOMMENDATION
I see a version of this all the time when I plan for clients.
Someone might come to me thinking they need an itinerary or a list of places to go. But planning a great experience is rarely just about finding good places. It’s figuring out which ones make sense for the person taking the trip—and how those choices fit together.
That’s why I spend so much time at the beginning of planning trying to understand the person I’m planning for. What do you enjoy? How do you like to spend your time? What have you loved—or disliked—on previous trips? Where do you want to splurge? Where don’t you care as much? How much structure feels helpful?
Those answers give me something much more useful than a longer list of possibilities: a way to evaluate them.
A highly rated hotel can still be in the wrong location for the trip you’re planning. A restaurant everyone recommends might not work with the rest of your evening. A popular tour might be a great experience and still not be the experience you want.
None of those things make them bad recommendations.
They just might not be right for you.
WHEN INSPIRATION STARTS TO LOOK THE SAME
There’s another part of this that I find interesting.
The more our travel inspiration comes from the same feeds, creators, search results, and recommendations, the easier it becomes for all of us to end up with some version of the same list.
You can see an extreme version of that in destinations that suddenly become social-media landmarks. In January 2026, Reuters reported on the effects of overtourism in Italy’s Dolomites, where places including Seceda and Lake Sorapis have drawn growing crowds after being amplified on Instagram and TikTok. The result has included traffic, litter, and trail erosion.
Over tourism is a much bigger issue than what shows up in our social feeds. But there’s something about this example that sticks with me: the tools that give us access to more travel inspiration can also lead more of us toward the same experiences.
And I think there’s a side to this issue that’s worth considering when we plan our own trips.
When everyone has access to the same inspiration, how do you make sure you’re planning the experience you want instead of simply recreating the experience you’ve seen?
That’s not to say you should skip the main attractions. I see it as my job to figure out how to make them work for you. You should absolutely stand at the feet of the Statue of David, but let’s get you there before the museum opens and the crowds arrive. Want to eat at a specific Disney dining option? Let me chat with my colleague who has worked at the park for over a decade to help us time it right. And if a must-have attraction sells out within moments, I can turn to my network to find another way in.
I don’t think the answer is avoiding popular places or experiences. Places become popular for a reason, and sometimes the thing everyone tells you to do is exactly the thing you’ll love.
But popularity alone doesn’t make something a must-do.
The more useful question is whether it belongs on your trip.
MORE OPTIONS CAN CREATE MORE DECISIONS
My least favorite question in any Facebook travel group is, “I have a week in [INSERT COUNTRY]. What should I do?” It’s not a bad question. The problem is that it usually leads to hundreds of recommendations based on what other people loved—not necessarily what will matter to you.
Having more information doesn’t necessarily make the decisions easier.
There might be thousands of tours available for a single attraction. You could spend hours comparing them and still wonder whether you picked the right one.
When I’m planning for a client, they don’t need me to hand over everything I found. My job is to do that sorting before the decision reaches them: look at timing, needs, price point, reviews from other travelers and advisors, the kind of experience they’re looking for, and everything else we’ve already planned, then narrow the possibilities to the few that actually make sense.
The client still makes the final choice. They just don’t have to make every decision required to get there.
That’s an important distinction for me.
Good planning isn’t about taking someone’s agency away. It’s about giving them better decisions to make.
THE BEST CHOICE HAS TO WORK WITH THE REST
There’s also a reason I don’t think planning can be reduced to finding the “best” hotel, restaurant, tour, or experience.
None of those choices exists on its own.
Where you stay affects how you get around. The timing of one activity affects what makes sense before and after it. A late dinner might be perfect one night and exhausting after a full day of sightseeing. The needs of one traveler can change the rhythm of an entire trip.
My brain naturally works like a whiteboard. I’m constantly thinking about those connections and how one decision affects another.
Planning well means looking beyond whether an individual option is good and asking whether it makes sense as part of the whole.
That’s something a recommendation on its own can’t answer for you.
And as the tools available to travelers keep getting better, I think that distinction becomes more important—not less. We have increasingly sophisticated ways to find ideas. The harder part is deciding which ideas deserve a place in the experience we’re trying to create.
AI tools absolutely have their place—for inspiration, organizing thoughts, and finding the highlights. More than once, a client has come to me with an itinerary outline that started with ChatGPT. For a recent family trip to Italy, that outline pointed them towards wineries in Tuscany by car or private driver. But during our Visioning Session, they mentioned a comment that stuck with me: “It would make our dad’s life if you found a way to get him on the back of a Vespa.”
That is how we landed on a full-day, semi-private wine tour where they each drove their own Vespa through the Italian countryside. ChatGPT gave them a starting point. Getting to know them helped turn it into an experience that was truly theirs.
THE TAKEAWAY
I don’t think we need less travel inspiration. I think we need to be more intentional about what we do with it.
Save the hotel. Send your friend the restaurant. Screenshot the itinerary. Ask AI for ideas. Keep the list of places you saw on TikTok.
Then ask yourself why you saved them.
What about that experience appealed to you? Does it fit the way you actually like to travel? Does it work for the people you’re traveling with? Does it make sense alongside everything else you want from the trip?
And perhaps most importantly: if you took away the fact that everyone else seems to be doing it, would you still want to?
I love the art of the possible. What I love even more is turning the art of the possible into reality. My role as a planner is to cut through the noise, understand the landscape to know what fits, and make it a reality.
Inspiration can give you somewhere to start. The choices you make from there are what turn it into a trip that is specifically yours.
