5 Reasons You Should ALWAYS Plan Your Trips

It’s late. You’re tired. You have been travelling for the last 24 hours and hardly slept on the flight. You are surrounded by people. EVERYWHERE! You are at a hotel asking for a room for you and your friends for the night. Guess what??? They’re booked out.

Yep, you arrived in Venice thinking that there would be an abundance of hotels available because there are a lot of hotels here. But this is already the third hotel you have tried and no luck. While you traipse in and out of hotels, your friends are on their phones frantically searching booking sites for availability, somewhere, anywhere! What were you thinking? Why did you not have something organised?

OK, this scenario is a little extreme. But I have heard of people arriving in a foreign country and then looking for somewhere to stay. More often than not they have organised their first night, so this drama doesn’t take place, but you still run the risk of doing the same thing the very next day.

So what should you do? In this article, I share with you the reasons you should always plan at least part of your trip before you jump on that plane.

I know for some you are worried that if you over-plan everything, it will take the spontaneity out of the trip, or that you will get stuck somewhere you don’t like. I get that. But if you are anything like me the above scenario would freak me out. And that is not how I want my precious holiday to begin. If planning a trip sends you into overwhelm, you might like my Travel Planning Guide – Getting Started.

Let’s not forget that travel should always be an adventure, but it does depend on your personality and how adventurous you want to be. So for those of you who don’t like surprises, especially when you are in the grips of exhaustion and jet lag, preparation is your friend.


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If you don't plan your trips you could miss out on some amazing things. Here is a guide to why and what you should plan before you travel.


1. No Room for the Night

You are heading to a well-known destination that you know has hundreds of hotels. You are not that fussy, so you feel confident that you will easily find somewhere to lay your head. At least for the first night and then you can reassess in the morning.

But come morning, you don’t want a room that is tiny and not so clean, perhaps the breakfast is far from adequate, maybe it’s the opposite and more than you need.

Whatever the drama that could come your way from only booking one night, you are hell-bent on having the freedom to choose. This is what travel is all about right?

But think again. Is it peak season? Are there any festivals and local holidays on? Or did you underestimate the number of people visiting that particular destination?

Whatever the reason, I would highly recommend booking accommodation for at least three nights and when you are booking check out the possibility of extending your time there, just in case you love it. Which leads us to our next point.


If you don't plan your trips you could miss out on some amazing things. Here is a guide to why and what you should plan before you travel.


2. Continuity

You may love the place you booked on the first night, but that’s it. No more availability and no amount of begging or pleading will find you an empty room. You have no choice but to head out to find something else. And guess what? Everything nearby is booked out. If you’re lucky, you will find another place, but they only have a room available for a night or two. Which means you will be looking for accommodation all over again in a few days. So now the place you loved and the area you wanted to explore is not an option because you have to move on.

OR you might find new digs, but they are not really what you are happy with, in fact, it’s quite awful, but now what choice do you have?

By booking your accommodation in advance, you will have the freedom and luxury of time to relax in your surroundings. You won’t have the stress of having to look for another hotel. And instead of wasting time on a computer planning your next move, you will be out and about enjoying all your destination has to offer.


3. Blowing your Budget

You have a travel budget that you need to stick to. In fact, it’s quite tight and you thought by not booking something that you would be locked into you could find something even better.

From experience when you are feeling under pressure to find a place to sleep and running out of time you tend to take whatever is available. And that could be a costly exercise. Because what if your budget allows no more than $200 per night and the only hotel room you can find is over $300 per night. Budget is blown on the first day!

Some wise planning and clever money saving ideas could be your saviour.


4. Time Efficient

If you have only booked your first night or even a couple of nights, and you hate it and want to move on you need to spend time the next day looking and then moving. The same goes if the accommodation doesn’t have any extra nights available to extend your stay if you like it.

For me, that’s precious time taken from sightseeing and relaxing and enjoying my time in my new surroundings to have to research and plan my next move. Research and planning that I could have done at home before I left.

If you do your research thoroughly, then you should be able to find something that you will like.

Become a sleuth. Websites like TripAdvisor are great. You do have to realise that these reviews are subjective, but I look at the overall comments. You could have nine great reviews and one negative. I will take the overall opinion of nine. I also advise taking the time to read each of those comments and more. These comments are where you pick up the little nuggets of gold so to speak. Where people talk about the restaurants they visited and loved, what the customer service experience at the hotel was like, the shops they recommend, directions to get there plus so much more.

You now have a picture of the accommodation you would like to stay in, and all it took was some time before you left.


If you don't plan your trips you could miss out on some amazing things. Here is a guide to why and what you should plan before you travel.


5. Don’t miss out

You may be going on holidays. You may be free every day to do whatever you like. But your destination is not. If there are certain things that you want to see or do in a particular destination and figure you will just organise it when you are there, then the least you should do is check for open days.

Some tours only run at certain times on particular days. Museums and galleries usually close at least one day per week.

How long are you staying in one place? How important is it that you visit this site or do this activity?

There is nothing more frustrating than wanting to do something, only to realise it is closed on the one day you had free or that it will be open on the day you leave.

You don’t have to have it all planned and booked, but at least note the days and times your “must see” activities are operating.


If you don't plan your trips you could miss out on some amazing things. Here is a guide to why and what you should plan before you travel.



Travel and planning also come down to the sort of person you are. Do you stress and worry easily? Do you suffer from anxiety? Are you casual and carefree?

Make sure you are perfectly honest with yourself and try to imagine some worst case scenarios. If you think you can handle it then maybe winging it is for you. Just remember this sort of travel is fraught with what if’s. Let’s face it all travel has what if’s, and travel plans, no matter how well organised rarely run smoothly. That’s the nature of travelling. But how much uncertainty can you cope with?


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Deciding to Wing It

If you do decide that winging it is for you, then you should consider the following:

The luxury of time

Is this your annual two-week vacation and time is precious? If the answer is yes then winging it may not work to your advantage. However if you have a month or so and you want to see where your travels take you then yes, of course, go for it.

Research and research

Research doesn’t sound like winging it, but you should at least know where you would like to go, what hostels and hotels are available. Formulate a small plan for your arrival until you get your bearings. Researching will give you the knowledge to move bravely forward. And you will know the main things you want to see and do when you get there.

Be flexible

Know yourself well. What will you or won’t you put up with? If you are not totally flexible, then I would suggest you become a planner and forget about winging it. If you are someone who is fussy, then you should never wing it. Too many things could go wrong and your holiday could turn into a nightmare.



There is nothing wrong with playing it by ear. In fact, many swear it is the only way to travel. It doesn’t matter what type of traveller you are, but it is important, to be honest with yourself.

My favourite saying is “Over plan and then go with the flow”. Because stress and anxiety can make my life a little miserable at times and over planning keeps them at bay, but then I am happy to throw the plan out the window once I have become comfortable in my new environment.

As you grow more confident, planning will become easier, and you can be more flexible and open. And who knows? One day you may become that person who just jumps on a plan and goes for it! Either way, have fun!



What sort of traveller are you? I would love to hear how you prefer to travel and why? Share in the comments below.


Cindy x


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Cindy Reid

Cindy is the founder of Travel Charm and her exclusive Travel Club. She is passionate about travel and planning and loves nothing more than helping travellers plan their best trips and fulfil their travel dreams.

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