Planning ahead of time is a sure-fire way to ensure that things go wrong.
Rarely does one formulate a plan and then proceed to flawlessly execute said plan (especially in the world of travel).
My philosophy is simple: if you don’t have a plan, then nothing can ever “not go according to plan” (for those who struggle with double negatives: if you don’t have a plan, then everything goes according to plan).
My travel nightmare (well, not my nightmare (that would involve bears and robots), but let’s call it a “least desirable scenario”) would be to have all my plane tickets, lodging, tours, transportation, and visits planned prior to walking out my front door. One of the aspects of travel that I enjoy most is the freedom to do as I please. To move about freely from place to place, to try out different hostels and hotels, to get local feedback on attractions and tours, to decide spur of the moment to hop on a train to a neighboring country – because that’s what travel is all about.
Now before you get upset, I am not saying that I foolhardily venture out into the world without having done my research beforehand – research and education are the keys to successfully traveling in this fashion.

THE ART OF ADAPTATION
In order for this strategy to work, you need to be adaptable.
Adaptation is an inherent part of travel. The same food, services, and luxuries you are used to back home, are not going to be readily available to you. However, adaptable does not simply mean that 400 instead of 800 thread count sheets are okay with you.
Instead it means that you can go to sleep after a night of exploration (read: heavy drinking with the locals), wake up before checkout, pack your things, move to a new place, enjoy a full day of activities, and then repeat. It means that you are able to make spontaneous decisions without having to rearrange your itinerary as a result, and that if your new friend wants to take you to their home tomorrow for a home-cooked meal, then you are ready, willing, and most of all able to do so.
It may sound appealing to book a hotel for six nights ahead of time and know where you will be staying, but what if circumstances change? What if the hotel’s toilets have no seats? What if the included continental breakfast was a sham!? If you’ve only committed to one night at the hotel, then you can easily move on in the morning without having to worry about cancellation fees or losing deposits.

NO PLAN BENEFITS
Not having a concrete itinerary only adds to the adventure that is traveling.
I love the freedom of meeting new people, finding out what they are up to, and then joining in should it fit my agenda. Trying to plan a trip ahead of time can (and will) result in you doing everything you “planned” to do, but not everything you ended up wanting to do.
When you have a “plan” it can seem as if you are touring a place as a museum exhibit instead of experiencing that place as a local. Spending your days surrounded by other tourists being chaperoned around by your “guide” is a travel sin, and will result in you fabricating and embellishing tales for friends and family since you have failed to experience anything genuine on your trip. By guessing and booking everything ahead of time, you are going to miss out on the true offerings of your destination.
Weather is a perfect example. If the anticipated weather decides to turn, then you may end up losing out even more. Rain today? Looks like you can’t go hang gliding. What’s that? No unplanned days to fit it back into your schedule? AND you lost your deposit? Wow, sucks to be you. Next time don’t plan so hard.
TOP REASONS NOT TO PLAN

- No need to worry about cancellation fees
- You’re not tied to some guesswork you did ahead of time
- You have the freedom to be spontaneous
- You’ll end up seeing more of what you want to see
- You’ll learn to rely on your instincts and you’ll learn to adapt
Granted, sometimes you will need to obtain visas, permissions, clearances, or some sort of confirmation prior to either arriving at your destination or participating in some activity (elections). But when it comes to “planning your trip”, you are better off letting it develop organically. Again, that does not mean you do no research ahead of time; research is your most valuable asset while traveling, and your being educated it what allows you to be so flexible in your travel plans.
Don’t be a slave to your itinerary.