Stop Planning the Vacation You Think You’re Supposed to Take

I plan vacations for a living, and the more I do it, the more I realize we’ve gotten something wrong about the way we travel. Not because we’re visiting the wrong places, spending too much money on hotels, or booking the wrong tours. Actually, it’s almost the opposite. I think we’ve gotten so used to being told how we’re supposed to travel that we’ve stopped asking ourselves a much more important question: What do I actually want from this vacation?

Open TikTok or Instagram while planning a trip, and it won’t take long for the algorithm to start force-feeding you everyone’s list of the “10 MUST-SEES IN ROME.” Don't get me wrong—I don’t think that’s necessarily a bad thing. Social media can be an incredible travel-planning tool. It can introduce you to a restaurant you never would have found, a neighborhood you didn’t know existed, or an experience that becomes one of the highlights of your trip.

But should we really let someone who visited Rome once, for two days, decide what you absolutely have to see while you’re there?

Somewhere along the way, travel became a checklist. Trevi Fountain. Colosseum. Vatican. Photo eating pasta. Photo throwing a coin into the Trevi Fountain. Then Florence. Then Venice. Maybe we can squeeze the Amalfi Coast in there too. Before you know it, the vacation you’ve dreamed about for years has become an endurance sport.

I understand why we do it, especially as Americans. Vacation time can feel incredibly precious. Many people get very little paid time off, if any at all, and even when we do have vacation days, we live in a culture that can make us feel guilty for actually using them. When you finally get that week to go to Europe, it’s easy to start thinking, This could be a once-in-a-lifetime trip. I need to see everything. I need to make it worth it. I might never be here again.

The problem with approaching a vacation that way is that you can come home having technically seen everything while feeling like you didn't really experience much of anything. You saw airports. You ran through train stations. You checked into hotels and checked out again. You got your suitcase wheel stuck in the cobblestones, took the pictures, checked the attraction off the list, and immediately started thinking about whether you were going to make your next train. Technically, you visited five cities. But were you ever really in any of them?

I’m not suggesting you shouldn’t live it up, especially if you really might only visit a destination once. See the things you’ve dreamed about seeing. Eat the food. Stay out late. Take the pictures. Just slow down enough to actually be present for it.

Start With the Feeling, Not the Destination

One of the biggest things I’ve learned as a travel advisor is that the destination someone initially asks for isn't always the destination they're actually dreaming about. Someone might come to me and say, “I want to go to Rome, Florence, and Venice.” Great. All three are incredible cities. But before I start putting together an itinerary, I want to know more. How do you want to feel on this trip? What do you picture yourself doing? What does your ideal morning look like? What about your afternoon or evening?

Sometimes the answers paint a completely different picture.

Imagine someone tells me they want to visit Rome, Florence, and Venice, but when I ask them to describe the trip they see in their head, they say, “I imagine myself sipping a spritz under a lemon tree overlooking the sea.”

Okay. We need to talk.

The vacation they’re describing and the itinerary they originally requested aren't necessarily the same vacation. That’s exactly why I don't believe there is a “perfect Italy itinerary,” even for first-time visitors. Someone who dreams about seafood, beaches, and lazy afternoons by the water probably shouldn't receive the same recommendations as someone who has spent their entire life dreaming about Renaissance art. Someone fascinated by ancient history shouldn't get the same itinerary as someone whose primary goal is to drink incredible wine and eat their way through small Italian cities. And if someone tells me they desperately need a quiet, relaxing vacation, I'm probably not going to drop them into the middle of Naples with a list of the city's busiest pizzerias.

The best vacation isn't the one everyone else says you should take. It's the one that actually fits you.

Social media has complicated that because we don't just experience places anymore; sometimes it feels like we need evidence that we experienced them correctly. We want the perfect photo of Italy. We want the restaurant we've seen 47 times on TikTok. We want the exact viewpoint from the Reel we saved six months ago. Did you really go to Rome if you don't have a picture tossing a coin into the Trevi Fountain?

Meanwhile, there might be a line down the street for the restaurant everyone saw online while a little place around the corner—maybe without an English menu and definitely without a social media strategy—is sitting there waiting to give you one of your favorite meals of the trip.

Again, I'm not anti-social media. Far from it. And I'm definitely not suggesting you should skip the famous places just because they're famous. I've been to Paris a number of times, and standing in front of the Eiffel Tower is still incredible. There's something almost surreal about seeing one of the most recognizable landmarks in the world—something you've seen in photographs and movies your entire life—suddenly standing right in front of you.

But when I think about Paris, one of the memories that comes back even more strongly has nothing to do with a famous landmark. It was dinner at a small restaurant on a corner in a lesser-known arrondissement with friends. We shared delicious food and a bottle of wine, laughed, talked, and simply enjoyed being together in Paris. There wasn't anything to check off a list. It was just a really good moment, and years later, that's one of the versions of Paris I remember most.

That's the balance I think we're losing. Go see the Eiffel Tower. Take the picture. But don't become so focused on experiencing the Paris you've seen online that you miss the chance to experience your Paris.

How To Plan A Vacation...But Not Too Much

This might sound strange coming from someone whose job is literally planning vacations, but I don't think every minute of your vacation should be planned. I'm also a Virgo, so understand that saying this represents significant personal growth.

I like structure. I want to know where I'm staying. I want transportation to make sense. I want important reservations handled ahead of time, and if there’s something I absolutely don't want to miss, I want it booked. A good plan removes stress. But I've learned there is a point where planning stops making travel easier and starts getting in the way of actually traveling.

One guideline I like is one major activity per day. If you're in Rome, maybe today is your Colosseum day. Go see the Colosseum. Learn something. Take your time. Appreciate the fact that you're standing somewhere you've seen in history books your entire life. But that doesn't necessarily mean you need three more timed attractions immediately afterward.

If a trip is longer than five days, I also love building in a day somewhere in the middle where almost nothing is required of you. That's not the day you visit the Vatican Museum. That's the day you wander through Trastevere with the only real plan being that you eventually make it to the aperitivo spot your travel advisor very strongly suggested. You stop somewhere because it smells good. You sit down when you're tired. You order another coffee. Maybe you go back to the hotel and take a nap. Maybe you stumble across something you didn't even know existed.

That's a vacation day too. In fact, it might end up being your favorite one.

There’s an Italian phrase I love: il dolce far niente, the sweetness of doing nothing. Spending time in Italy has made me appreciate the idea more and more. Doing nothing doesn't mean you're wasting your vacation. Sitting at a café isn't wasted time because you could have squeezed another museum into that hour. Walking without a destination isn't wasted time. Having a long lunch isn't wasted time. Sitting somewhere beautiful and doing absolutely nothing except realizing, Holy shit, I'm actually here, isn't wasted time.

There Is No Right Way to Vacation

I don't want to replace one set of travel rules with another. I'm not going to tell you that the correct way to vacation is sitting under a lemon tree drinking a spritz—although, for the record, that sounds pretty great (and it is).

Your vacation should be whatever you need from it at that point in your life. I've had times when I wanted adventure, and I've had times when what I needed was to hike 12 miles a day, think, experience nature, and be alone with my thoughts. Sometimes you need a beach chair and absolutely nothing else. Sometimes you want museums from morning until night. Sometimes you want nightlife, food, nature, history, or to wake up without an alarm and decide what you're doing over coffee.

None of those are the wrong way to travel. The mistake is assuming someone else gets to decide which one you need.

So before you open Google Flights, search for the best European destinations, or save another list of “must-see” attractions, I want you to try something different.

Close your eyes and picture yourself on vacation. What do you see? What does the air smell like? What can you hear? What are you eating? Are you surrounded by people or somewhere quiet? Are you looking at the ocean, walking through a city, drinking wine in the countryside, or staring at something you've only ever seen in a history book? Are you exhausted at the end of the day because you spent 12 hours exploring, or are you barefoot on a balcony wondering what you're going to order for dinner?

Most importantly, how do you feel?

Maybe you feel relaxed. Maybe you're curious, adventurous, connected, or inspired. Whatever the answer is, I think that should be the starting point for planning your vacation—not TikTok, somebody else's bucket list, the itinerary your coworker followed three years ago when he went with his four kids, or even a travel advisor telling you there's one “perfect” trip everyone should take.

A great vacation should have enough of a plan that you don't have to spend the entire trip worrying about what happens next, but enough freedom that something unexpected can happen. So yes, go see the Eiffel Tower. Stand inside the Colosseum. Throw the coin into the Trevi Fountain if you've always dreamed about doing it. Take the picture.

Then put your phone away, turn down a street because it looks interesting, sit at the little restaurant around the corner, order another glass of wine, and stay longer than you planned.

Because I think we've forgotten that the point of taking a vacation isn't to prove how much we saw. It's to actually experience being there.