To Plan or not to Plan?

It seems to be a popular topic of late. To plan or not to plan seems to be the big question. Travel Planning is my speciality so it wouldn’t be a huge guess that I am by nature a planner. I even plan our weekends away.

And I have a good reason which I will cover soon.

But here’s the thing. I get why having a plan can suck. Big time. I see people who have become slaves to their itineraries and they seem to be missing the whole point of travelling at all.

You see my favourite saying – “Over-prepare and then go with the flow”, comes from my necessity to plan, for personal reasons, but it goes on to capture the magic of travel.

The moments of pure delight that happens when you go with the flow.

I believe that it’s a balance for most of us. As most things are.

We should let people be and do what they need to do. I don’t think it’s up to any of us to tell people how they should travel.

Growth is a part of life, or at least it should be. Travel is no different. We learn as we go. And the only way to go is any way we can.

It’s one thing to share your experiences. It’s another to tell someone to do it the same way. Because one person may be an extrovert and ready to tackle the big crowded noisy world head-on, another is an introvert quietly reflecting, taking their time to work through new surroundings. Throw fears, anxieties and preconceived ideas into that mix and you have even more to contend with.

Nothing is right or wrong. Just different. One size certainly doesn’t fit all which is apparent when you have solo travellers and tour lovers.

Each to their own and so it should be.


Should Travel Planning be your priority? Or maybe just see what happens without a plan? #traveler #itinerary #travelplanning


How not to plan your itinerary

I am contradicting myself here by saying you can’t tell someone else how to travel. So let’s just say this is useful advice to be taken into consideration.

Sounds strange coming from a Travel Planner that I would tell you how not to plan an itinerary.

The reason I am passionate about helping people plan their travel, and yes I even include Daily Schedules (don’t freak out all you fly by the seat of your pants travellers!) is that it helps my clients strike a balance between over-planning and under-planning.

You don’t want to become a slave to your itinerary. But you may travel planning to help you on your way.

Here are the main reasons people over-plan an itinerary.


Time constraints

A lot of people can only travel for a limited time once a year or even less. That means that most believe it will be the one and only time they will travel to a destination.

Or they have saved for years for this once in a lifetime trip that they have been dreaming about forever and are yet to learn they can afford to travel more than they think.

So, they cram it all in.

I have met families travelling that are so exhausted, the kids are miserable and complaining because they have stuffed so much into their itinerary.

Kids and adults need downtime. Rushing from one tour to another, coming in late and rushing off early does not allow you to enjoy the moment. It means you are clock watching. Who wants to do that on holiday?

You need to understand something.

You CANNOT DO IT ALL! OK, maybe I can reword that. You could do it all but will you enjoy any of it?

I discuss what to do further down.



Money can be a struggle. And if you have taken a long time to save the money for your big trip you might be very conscious of stretching your travel dollars as far as you can.

For some, that means watching everything! Every single cent. And that in itself becomes as much as a headache as packing an itinerary too full. They over plan so they can keep a tight reign on the budget.

You can easily work out an average daily budget. For the first few days keep a tally of what you have been spending and adjust accordingly.

There are many clever money saving ideas that will still allow you to have memorable travel experiences without breaking the budget.

Join free walking tours instead of paying for organised tours. Or print out self-guided tours, or create your own. I have created a stack of downloadable itineraries for people to follow. It makes travelling a little easier.

A planned itinerary can help you stay on budget, but it needs to be flexible and not have you up in arms every time you want to splurge on a gelato.

I even have a Budget Planner you can use to document your expenses. You can determine what will be prepaid, what you will have to pay for whilst you travel and then see what you have left for spending.

You can read up on how to plan your budget with ease here.

By the way, don’t ever skimp on Travel Insurance. Ever!


Fear and Anxiety

This is the reason I learnt Travel Planning.

Without a fully planned itinerary, my anxiety would have got the better of me and I would have backed out. Planning was my saviour.

By planning, I didn’t have to stress each day working out what I was going to do. By having the steps laid out in front of me it gave space for my confidence to grow. All of my decisions were made at home when I had time to research. Not made when I am tired, jet-lagged and possibly anxious in a new environment.

I have written about anxiety and travel. It’s no picnic, so if I can do anything to help myself and others get on a plane and start travelling, then that’s what I’ll do.

If over planning means that you will actually travel opposed to staying fearful and staying home, then over-plan. Definitely over-plan!

Once my confidence grew I could relax and let go.

In the end, and after travelling for a month, the woman (me) who previously was too anxious and fearful to do anything on her own, both at home and travelling, was begging her family to go out for day trips without her. Simply so she could enjoy time on her own doing her thing.

Each time you travel will be easier. Eventually, your itinerary does not need to be so scheduled. You might even become one of those people who doesn’t travel with a plan at all. Bravo to you!

Or like me, I always like to be organised. Let’s face it I am a dedicated list lover and I don’t see that obsession ending anytime soon. But I am an expert at going with the flow too, so perhaps I have achieved the perfect balance, for me.



Planning a good itinerary (for those that need one)

Activities & Sightseeing

Pick three or four things in your destination that you really want to see or do. Work those into your itinerary.

Create a list of other things you would like to do, but are an absolute must. That way if you find you have time on your hands and want to fit something else in you have your list. If not, you have seen your top four things and get to explore where the mood takes you.

Maybe visit a wine bar you saw while you were out walking or visit a market you spied a few days before. Or the concierge at your hotel told you about a delicious pastry you can only get at a small hole in the wall place and only made in that location. Or just go out, walk and see where it takes you.

But do not cram every second of your trip with tourist attraction after tourist attraction. By doing this you might not find the authentic travel experience you were looking for. And you might be too exhausted anyway!


How to Prioritise your Activities

Do you really need to go into every church? Visit every museum? Even if they come up on the “10 Must-See Places in  _____”.

The other thing I am not a fan of is “commercial” tourist attractions you see all over the world. By that I mean places like (and sorry if I offend), Hard Rock Cafes, Madam Toussads, Ripley Believe it or not, well, you get my point.

The rule I had for the kids, and I was that if we visited something it needed to be unique to our destination. Something we could only experience at that destination. The only time I have swayed from that rule was in Amsterdam when I took the kids to the Dungeon because my son (age 12) had been getting bored with all the sightseeing. Yep, I did the bad parenting thing. I bribed him. Sometimes you just have to do these things.



I am a great believer in Slow Travel and I have learnt that it is better to choose fewer destinations and stay for a longer time so that you can explore more, not have to pack up every few days which is costly and tiring, and you can get to know a place on a deeper level.

I also make sure that every itinerary I plan, including those for myself, has free time. It could be an hour or two, or a free morning or afternoon, or an entire day.

My itineraries for my groups were exactly the same.

I might need time to nap. I mean why not? When in Italy, why not adopt their habits? Jetlag can be a killer too and I am not at my best tired so I have absolutely no problem with the idea of taking a nap. Do what you need to do.

Some in our group would take it easy during free time, read, catch up on news from home and others were able to fit more in. Everyone is different and downtime, or free time, allows you to be flexible.


Should Travel Planning be your priority? Or maybe just see what happens without a plan? #traveler #itinerary #travelplanning


When Confidence Grows

After a few times, or once might be enough, of travelling with a strict itinerary you begin to understand that everything is ok, that you handle travel well. You might even start to feel trapped by your itinerary.

If you want to travel, and you want to plan, then plan. If that means someone says you’re over-planning, don’t listen. It has nothing to do with them.

My only words of advice, don’t get too bogged down with the little details.  You can send yourself crazy worrying about where you will exactly meet a tour guide or how to get the best price, for the best tour.

Go with what you think is best at the time, be happy with your decision and be done with it. The tiny details will be your undoing. That’s when over-planning can be detrimental.

You can always join one of the many Facebook Travel Groups whose members are happy to help and give advice. You can join mine here if you like.

Read all your information. If you don’t know something, ask someone. A hotel concierge, shop assistant, a waiter. Just ask. Someone will help you. I have never not been assisted by someone in a foreign country.



My confidence increased. In travel and life in general. Thank goodness. It only took 49 years! But to this day I will always make a plan. Because that gives me the confidence to know I can tackle what comes along. Because if my anxiety hits, I don’t think very clearly. And by having an itinerary or plan in my hand I don’t have to think, I just have to do.

There are days I throw it out the window and do something random or not much at all. On those days when travel plans get the better of me, I like nothing more than to grab a notebook, head to a favourite café and write. Or people watch.

And that’s what travel should be. At least for me. Not a manufactured, timed to perfection, see everything on the list experience. And that’s what I think people mistakenly think you create when you tell then you plan travel.

The magic that travel gives us comes from unexpected moments, random interactions and time on your own.

My most poignant moments in travel would sound mundane and boring to another person, but to me, they are tiny sparks of joy that ignite my passion to explore more of this world and the people that inhabit it. Sure, I do some of the tourist stuff.  Those things can be interesting, but not magical.

It’s the magic that I seek, each and every time.

And that is what your travel goal should be, to find the magic.


Cindy x



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Hi there! I'm Cindy the founder of Travel Charm. About 6 years ago I learnt to overcome anxiety to follow my travel dreams. And I haven't looked back! I would love to help you plan your travel so you can start living your dreams instead of just thinking about them.

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Cindy Reid

Cindy is the founder of Travel Charm and combines her passions of escorting small group trips for ladies who want to travel and travel planning. She loves nothing more than helping people fulfil their travel dreams.

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