What NOT To Do When Planning your Itinerary

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.

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 that’s what can happen if you take planning too far.

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.

Growth is a part of life, or at least it should be. Travel is no different. We learn as we go.

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.


Planning an itinerary can be overwhelming. Here is what NOT to do when planning yours. #travelplanning #itinerary #plantravel


3 Things NOT To Do When Planning Your Itinerary

These three things, in my experience, can kill a good 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 to strike a balance between over-planning and under-planning.

Below are the main things people do wrong, including me, when planning an itinerary.


1. Cramming Too Much Into Your Itinerary

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.

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?

Read on to find out how to address this issue.


2. Letting Your Budget Dictate Your Itinerary

Money can be a struggle. 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 of a headache as overpacking an itinerary. 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. 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.

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

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


3. Allowing Fear and Anxiety to take over

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, I had space for my confidence to grow. All of my decisions were made at home when I had time to research. Not made when I was tired, jet-lagged and 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.



3 Ways to Plan a Great Itinerary

1. Choose Your Activities And Sightseeing Carefully

Pick three or four things at 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 not 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 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!

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

If they are of interest to you, sure knock yourself out. But don’t feel like you have to.

I’m pretty sure none of the locals has been to every church, museum or tourist attraction in their city or town. If you are looking for more authentic experiences, think about what the locals do. Where do they hang out? Eat?

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 when we travelled was that if we visited an attraction it needed to be unique to the destination, or we didn’t have at home. The only time I have swayed from that rule was in Amsterdam when I took the kids to the Amsterdam Dungeon because my son (age 12 a the time) had been getting bored with all the sightseeing.

Yep, I did the bad parenting thing. I bribed him. Sometimes you just have to pick your battles.


3. Include Downtime In Your Schedule

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.

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 when I’m tired so I have absolutely no problem with the idea of taking a nap. Do what you need to do.

Free time can also mean you can use it to revisit a place you liked, add in another sight you hadn’t known about before you arrived, or read, catch up on news from home, do some laundry. Free time mean non scheduled time.

Free time allows you to be flexible and builds spontaneity into your travels.


4. Fewer places, more time = more exploring

Stay in fewer locations for a longer time and you get to see more? How?

I will give you an example.

If you stay in Florence for five nights, you can spend one day exploring the city, another doing a tour or a cooking class or something else of interest.

On the third day, you can do a day trip, leaving early in the morning to say, Lucca. Spend a full day exploring, stay for dinner and catch a train back to Florence.

The next day you can choose to explore more of Florence or do another day trip. Or join a tour that will take you to the wineries and some of the smaller villages.

And on the last day you can do the same again, perhaps sleep in, catch a train to Arezzo explore for the day and come back to spend the late afternoon and evening in Florence before moving on the next day.

You have only unpacked once and you have seen three different places plus Florence.

Of course, this is an example only.

But if you only stay a maximum in each location for two nights you only have one full day to see your destination, with no option but to move on.

By staying longer you have more choices and much less exhaustion and wasted travel time.


Should Travel Planning be your priority? Or maybe just see what happens without a plan? #travelplanning #itineraries #planningtravelAn afternoon in Arezzo, Italy checking out the Christmas Markets

When Confidence Grows

The more you travel, the more you will come to realise that you don’t need to be so strict with your schedule.

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.

But don’t get too bogged down with the little details.  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 my group here.

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.

Get the STEP BY STEP ITINERARY PLANNER including checklist and templates. CLICK HERE FREE DOWNLOAD

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 whatever comes along.

There are days I throw the itinerary out the window and do something random or not much at all.

And that’s what travel should be.

Look for those random, unplanned moments that just happen and are magical.

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


Cindy x

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

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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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