The Best Trip on Paper May Be Completely Wrong for You

You know what can make planning a really good trip surprisingly difficult?

It isn’t always finding good choices. Sometimes it’s having too many of them.

You start looking at hotels and find five that have great reviews. Then you watch a few videos, read another article, ask a friend who was there last year, and suddenly hotel number six has entered the running.

Now they’re all starting to look good.

So how do you decide?

This is where I think travel planning gets interesting, because the question really isn’t, Which hotel is the best?

It’s which one is best for you?

Those are two very different questions.

I can show two clients the exact same hotel and get completely different reactions. One may love that it’s tucked away in a quieter neighborhood. The other may look at me and say, “Marina, I don’t want to get in a taxi every time I want to go somewhere.”

Fair enough.

Neither person is wrong.

And that is why I ask so many questions before I start recommending things.

I’m not being nosy. Well, maybe a little. I’ve always been curious.

But I need to know how you actually travel.

Do you like getting up early and heading out, or is vacation the one time nobody better talk to you before you’ve had coffee? Do you like a full day of sightseeing, or do you hit a point around three o’clock when you are done and ready to sit somewhere with a glass of wine?

Those things matter.

Because I can build you an itinerary that looks fabulous on paper and still have you wondering halfway through the trip, Whose idea was this?

And that’s not what we’re going for.

A great choice isn’t automatically the right choice

A hotel is a good example because people tend to start there.

Maybe you’ve found a gorgeous property with wonderful reviews. The rooms are beautiful. The service sounds terrific. Everybody online loves it.

But then I start asking questions.

What do you want to be able to walk to? Do you like coming back to the hotel during the day? Are you someone who wants restaurants right outside the door, or would you happily trade that for peace and quiet?

Maybe a room with a view matters enormously to you. Maybe you’d rather put that money toward a private guide or a really special dinner.

And sometimes the thing that sounds insignificant while you’re sitting at home turns out not to be insignificant at all.

A walk-in shower, for example. An elevator. How far the room is from the lobby. Whether breakfast is available early enough for a tour day. Whether you need transportation every time you leave the property.

None of those things will make the hotel show up higher on somebody’s “Best Hotels in Europe” list.

They may make a very big difference to you.

And hotels are only one example.

Every destination seems to have something you’re told you absolutely must do.

I always wonder who decided that.

If you have been waiting your whole life to see a particular museum, then yes, let’s make sure you see it. But if museums aren’t really your thing, spending half a day in one because every article says you should is not necessarily the best use of your vacation.

The travel police are not going to come looking for you.

The same goes for restaurants, tours and attractions.

I have no problem recommending something popular when it fits the traveler. Popular things are often popular for a reason.

But “everyone does it” is not enough of a reason for me.

I want to know whether you will enjoy it.

And then there is pacing.

This is where a trip can get into trouble very quickly because everything looks easier on paper than it feels when you are actually doing it.

Three nights here. Two nights there. Train to the next city. Early tour the following morning. Another transfer. Another hotel.

Perfectly possible.

But do you really want to spend that much of your trip packing and unpacking?

There is a phrase I hear all the time when people are planning:

“We’re already there, so we might as well…”

Be careful with that one.

“We’re already there, so we might as well add Florence.”

“We’re already there, so we might as well squeeze in another island.”

“We’re already there, so we might as well take the 7:00 a.m. train.”

Before you know it, you need a vacation from the vacation.

Sometimes the best thing I can do for an itinerary is not add something.

That can be harder than it sounds, especially when this may be the trip you’ve been talking about for years. Of course you want to see as much as you can.

But seeing more and enjoying more aren’t always the same thing.

I’d rather have you come home talking about the afternoon you spent wandering through a neighborhood, finding a wonderful little café and having nowhere you had to be than tell me you made it to seven cities but can’t remember which one had the restaurant you loved.

When more information doesn’t make the decision easier

And this is where all that online research can start to work against you.

Not because research is a bad thing. I do plenty of it myself. But once you have 38 tabs open and every hotel has great reviews, more information doesn’t always make the decision easier.

Reviews are useful. I read them too.

But reviews tell you what mattered to that traveler.

One person says, “I loved how peaceful the hotel was.”

Another says, “The hotel was too far from everything.”

They’re describing the same hotel.

One person says an eight-hour tour was the highlight of the trip.

Another says it was far too long.

They’re both probably telling the truth.

So the more research you do, the more you may realize that the challenge isn’t necessarily finding good choices.

It’s deciding among a whole lot of good choices.

And that brings us right back to the original question.

Good for whom?

I think the same thing applies when you’re deciding where to spend more money.

I’m all for a good splurge when it makes sense.

The key words there are when it makes sense.

Maybe business class on a very long flight would completely change the beginning and end of your trip.

Maybe you couldn’t care less about the flight but would happily spend more for a private guide.

Maybe the hotel room with the view is the thing you’ll remember.

Maybe you’d rather have the standard room and use the difference for an experience you couldn’t easily have anywhere else.

There is no universal “worth the splurge” list.

If you don’t care about it, it isn’t worth the splurge simply because someone else says it is.

The trip should fit the people taking it

This is why so much of my planning starts with conversation.

I don’t just want to know where you want to go.

I want to know what you enjoy once you get there.

What do you look forward to most when you travel? What wears you out? What do you happily spend money on? What makes you think, I don’t care how highly rated it is, I am not paying for that?

Those answers tell me far more than a list of five-star hotels ever could.

And if you’re traveling with someone else, there is another wrinkle.

You may not travel exactly the same way.

One of you may want to be out the door at eight in the morning.

The other may consider eight in the morning a personal insult.

One of you may happily spend hours in a museum.

The other may love you very much and still be done after forty-five minutes.

That’s where thoughtful planning becomes less about finding “the best” and more about finding the balance that lets both people enjoy the trip.

There isn’t one perfect itinerary sitting out there waiting for you to discover it.

I actually think that’s good news.

It means you don’t have to travel the way your neighbor traveled, the way someone on YouTube traveled, or the way a magazine says you should travel.

You just have to figure out what matters to you.

And sometimes that means choosing the hotel that isn’t ranked number one.

Sometimes it means skipping the famous restaurant.

Sometimes it means spending another night in the same place instead of adding another city.

And sometimes it means saying, “You know what? That sounds wonderful. Just not for us.”

That’s not missing out.

That’s knowing yourself well enough to plan a better trip.

And to me, that’s the difference between a trip that looks great on paper and one that actually feels right once you’re there.

How you travel matters.

Ready for a little help sorting through the choices?

If you’re planning a trip and have reached the point where everything looks good, but you’re not sure what actually fits you, that’s often where I come in.

We can talk through what matters most to you, sort through the options, and build the trip around how you actually want to travel.

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