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  • Joanne Herd

The Myth of the Perfect Trip: Embracing Imperfections in Travel

Updated December 4, 2023

“A beautiful thing is never perfect.” ~Egyptian Proverb

If you’re anything like me, when you start thinking about your next trip you’re filled with excitement.

The world is an open book. There are so many things to see, places to go, and adventures to have. It’s a time of anticipation and optimism.

But then I start getting bogged down.

There are so many places to go, so many things to see, so many possibilities. How do I choose the right one?

What’s the best place to go right now? Is the weather good? Is it crowded? If I go in the off-season will everything I want to see be open?

This is the point where it’s all too easy to abandon the planning process because it’s just too complicated, there are too many options, too many questions, and I don’t have the mental capacity or time to deal with it.

Sound familiar?

Maybe that’s not you at all. Maybe you’re one of those people that can close their eyes, point to a place on the map, and just do it.

Or maybe you already have a list of places you’d like to go, so when it’s time to start planning you can just work your way through the list.

For those of us who do struggle with all the decisions that are part of travel, from where and when to go to where to stay and what to eat, here are a few reminders to help you out:

There’s no such thing as the perfect trip

There will always be more places to go and more things to see and do than we can possibly fit in.

Also, flights get delayed. Sometimes it rains. People get sick. Hotels get oversold.

It’s the simple truth. Things go wrong.

No matter how prepared or informed you like to be, you will never know everything about your destination before you go, and there will always be something you hear about later (sometimes right after you get home!) that you wish you’d known while you were there.

That’s ok!

If you really loved a destination you can plan to go back. You can see the things you didn’t see the first time.

That’s what I do when I go to Florence, Italy. It’s my all-time favorite destination and has been for years. Every time I go I see and do new things, and I still have a list of things I want to see on future trips.

Travel is a chance to expand our horizons and get out of our comfort zones.

To me the true measure of a trip isn’t if it all went according to a perfect plan and I saw all the highlights and checked off the “must-see” things. Instead it's measured by if I experienced each moment, good and bad, and have a mental suitcase full of memories at the end.

There’s no such thing as the perfect place

Every location has its pros and cons.

For example, I love New York City. I delight in the restaurants, museums, and the hustle and bustle of the city. I feel alive when I’m there.

However, I don’t love the smell in the summer, or the crowds of tourists who think that suddenly stopping in the middle of the sidewalk to take a selfie is somehow and ok thing to do (if you’re one of those people please remember that a “pedestrian flow zone” means keep moving, consider it to be a public service for the rest of us).

One of the great things about travel is that it’s temporary.

If you love someplace you can always go back! But you won’t love every place. There will be some that you say “yep, been there, done that, and I don’t need to go again.”

Does that mean it was a wasted trip?

Absolutely not!

You experienced something new and learned something about what you like and don’t like that will guide your decisions in the future. It’s always ok to consider something a learning experience.

There’s no such thing as the perfect time

My preferred time to go to most destinations is the shoulder season or the off season. For most of Europe that means fall, winter and spring (with the exception of the holiday season anywhere there are good Christmas markets).

Why do I prefer those times?

Simple, there are fewer people! I’m not someone who likes crowds, and waiting in lines or elbowing my way through streets is never how I’d prefer to spend my time.

There is a tradeoff though.

When I travel in the off season the weather doesn’t tend to be as nice, it’s cooler (which I’m totally ok with!), there are more cloudy days and it’s more likely to rain.

I’m ok with that, because to me that’s totally worth it.

You may feel differently. Maybe you want to travel during the summer when your kids are out of school and it’s easier for you to take vacation days from work.

There’s always a tradeoff no matter when you travel, the key is to find what works for you.

Memorable > Perfect

I’d rather have a memorable trip, whether those memories are great or not-so-great, than a perfect trip.

I remember in particular one bus trip that I took with a group of high school students. It was about a 22 hour bus ride, and somewhere around the middle of South Carolina in the heat of summer the air conditioner failed.

Let me say those remaining hours driving to Florida were hot, sticky, and not the most fun.

For years after that trip, however, it was the bus ride that still made for the most conversations. It brought us together and forged bonds in a way that a perfect trip never could have.

Isn’t that really what travel is about?

It’s about connecting in a real way. Connecting to yourself. Connecting to those you’re traveling with. Connecting with a new location and culture. Perfection does not create connection. Memorable experiences create connection.


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