Why you Shouldn’t Plan Out Every Detail of Your Trip

Why you Shouldn’t Plan Out Every Detail of Your Trip

How will you be able to embrace the unexpected on your travels, if you try to plan out every little detail?

Let’s be honest, how often have we tried to plan out a trip or an event down to the last possible detail, only to have something “out of our control” occur anyway? (Me 👋🏽.)

Don’t get me wrong, although I am not much of a planner at this point in my travels, I do get the importance of needing to plan out a trip to a certain extent. The extent being- getting your hotel room(s), knowing the area(s) you want to go, maybe picking out some places and experiences that you know you are “must tries” or “must dos” for your trip.

For many of us, planning out every detail of a trip provides a sense of control, a sense of order. It can be comforting to know exactly where you’ll be at any given moment and what you expect when you get there. However, for others, myself included, there’s an undeniable thrill in the unexpected, the possibility that around the next corner lies an experience you hadn’t anticipated.

Here’s are some reasons why leaving some of your travel plans to chance, can lead to the most memorable experiences:

Table of Contents

How will you be able to embrace the unexpected on your travels, if you try to plan out every little detail

  1. 1. When you don’t plan out every detail, you are able to “discover” Hidden Gems
  2. 2. When you don’t plan out every detail, you are able to build adaptability
  3. 3. When you don’t plan out every detail, you are able to deepen and find new connections
  4. 4. When you don’t plan out every detail, you are able to embrace your creativity and curiosity
  5. 5. When you don’t plan out every detail, you are able to have more freedom
  6. 6. When you don’t plan out every detail, you are able to have stories to tell
  7. 7. When you don’t plan out every detail, you are able to learn to trust yourself

1. When you don’t plan out every detail, you are able to “discover” Hidden Gems

I am not able to tell you the number of all the times I had plans, just to ditch them, because there was something else we were invited to do, or because we ended up finding something better or even just we tried to go or do what the plan entailed, but it left us craving more.

Typically, when we over-plan out a trip, we often stick to the tourist-beaten paths. I mean seriously, we have google researched all the reviews, read all the comments, looked at places with the highest ratings. However, I have come to realize, those paths are cool and they are popular for a reason, but they are not always the best for every tourist, and they are usually the most crowded.

Sometimes new paths are waiting for you to discover them! That may sound scary, sure, but where is the thrill in going to a new place, just to do the same thing or go to the same place everyone else has?

I do want to note to make sure the research you have done involves the areas you are going. It is natural to explore, but you don’t want to fall off the map- LOL. Just because you don’t plan out every detail of the trip, you still need to do your research and be smart.

I said all that to say, by leaving some space in your planned itinerary, you might stumble upon a charming cafe, an enchanting street performance, a boutique that resonates with your known or new-found style, an authentic local restaurant, or possibly one of the best parties you could ever experience —all away from the busy tourist hotspots.

Street performance

2. When you don’t plan out every detail, you are able to build adaptability

One of the reasons I love to travel is because, by nature, traveling comes with its set of unpredictable challenges and as a person who thrives from challenges, I almost expect them and thrive when they occur. These challenges can include missed or bumped flights, sudden weather changes, delays and cultural misunderstandings or differences.

By not planning every minute of the trip, we build resilience and adaptability within ourselves that allow us to learn to navigate and even somewhat appreciate unforeseen circumstances within our daily life.

Additionally, I always like to think of the following saying “Every rejection is protection”, which to me, means that sometimes when challenges arise, it is because you are being protected from an event or circumstance that you don’t need to face or be apart of. Also, as a reminder, just because you were in a rush or had your plans mapped out on your itinerary, does not mean the universe is also going to follow suit!

Check out this interesting story to see what I mean https://abcnews.go.com/International/dutch-cyclist-missed-doomed-malaysia-flights-feels-lucky/story?id=24652064

See how travel helps us heal.

3. When you don’t plan out every detail, you are able to deepen and find new connections

How many times have you heard the phrase “It’s not what you know, its who you know, blah, blah, blah? I used to absolutely despise that phrase until I grew up and realized how true it really was. As a self-declared introvert, the spontaneity of not having a plan for every detail of your trip can often lead to authentic interactions and conversations with people.

Instead of rushing from one scheduled spot to the next, you could end up having a long conversation with a local, or someone who may be a future business partner at a bar, or even joining a group of new friends for some kind of adventure. I have met many great people who have shared stories and exchanged lessons often leading to deeper and more genuine connections.

4. When you don’t plan out every detail, you are able to embrace your creativity and curiosity

When you’re not bound by an itinerary, you and your mind are free to wander. This spontaneous approach can ignite your curiosity and creativity to truly observe and experience all that you come into contact with during your exploration. You may decide to sketch a beautiful scene you stumbled upon or write about your experience, this type of travel nurtures the creative spirit within you.

5. When you don’t plan out every detail, you are able to have more freedom

Let’s face it: a packed schedule can be stressful. Having to worry about catching the next bus or making a reservation on time can really overshadow the joy of travel. Especially when as I mentioned before, not everything always goes the way it was planned.

When everything is not planned out, it allows for gaps in your schedule which ultimately provides you with the freedom to linger a bit longer at a mesmerizing site, float in the cool waters of the pool, sip on a couple more mimosas, or simply relax and enjoy the comfort of your hotel room.

6. When you don’t plan out every detail, you are able to have stories to tell

Honestly, some of the best travel stories arise from unplanned adventures, whether intentional or not.

For instance, getting lost in the maze-like streets of a market or town, discovering the best meal from a street kitchen, or stumbling upon a hidden waterfall while hiking—these events make for the most captivating stories.

7. When you don’t plan out every detail, you are able to learn to trust yourself

When you don’t have everything planned out, you’re pushed and in a way forced to trust your instincts and those gut feelings. This can lead to a profound sense of accomplishment and discovery within yourself. Learning to trust your judgment and decision-making skills in unfamiliar situations is an invaluable life lesson for use in anything you do and anywhere you choose to go.


In conclusion, while there’s no absolute “right” way to travel, there’s something genuinely magical about why don’t have to plan out every detail of your trip. By doing so, you open the door to unexpected joys, challenges, and memories that will last a lifetime, which is one of the main points of travel, right? Next time you think of packing your bags or are ready to, consider leaving some dates/times and pages of your itinerary blank and let your journey unfold on its own. Embrace the unknown for you—it might just be the most rewarding part of your trip.

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