Planning v.s Spontaneity, how best to travel

Should you plan your travels or be more flexible?

Planning VS Winging it: How best to travel

Travelers come in two tribes: those that are micro-manage with detailed itineraries, and those that winging it. In this article, we are going to run through the pros and cons of planning ahead v/s going with the flow.

If you plan your movements ahead of time you are likely going to face fewer surprises on your journey, unfortunately, this takes away an element of adventure, but where’s the trade off?



Booking accommodation ahead of time will ensure you get the pick of the best places to stay. Not being organized means risking having to stay somewhere less attractive which may still be expensive.

Winging it

In some less developed countries, not all hostels have online booking. The micromanager may end up staying in a big hotel chain paying 30 quid a night whilst you’re in a beautiful hut on the seafront for 10.



By planning your itineraries you are sure to tick off all the items on your bucket list, you’ve identified what a country has to offer and have scheduled your top picks accordingly.

Winging it

Micromanagers haven’t left any room to explore or change their plans to fit in with the itineraries of others. You are free to follow your mood and your friends, and see where it takes you.



Booking flights ahead of time means you’ll get a cheaper fare on a better flight – whether that means fewer layovers or simply a nicer airline, it pays off to book ahead.

Winging it

What happens if a Micromanager wants to stay somewhere a bit longer or go somewhere else entirely? Some airlines won’t allow refunds or exchanges so they will either lose money by changing it or miss out on doing something new. By not booking too far ahead you’ve given yourself flexibility and time to change your mind.

Money management


There nothing worse than having to cut your trip short because you’ve run out of money. By creating a budget and sticking to it you know that you’ll be able to make it to the end of your trip without becoming broke, or even worse – in debt.

Winging it

People that stick to stringently to their budget may miss out on doing once in a lifetime things that may cost a bit more, for example doing a PADI dive course, or bungee jumping. Don’t be reckless and do consider your means before spending money, but don’t limit your adventure with financial worries.

So there we have the two sides to the story. I think there is a happy medium to be found in both and that there are certain situations where it pays off to align more with one school of thought, but now it’s up to you to decide what you prioritize: a safety net or adventure?

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