How to Turn an Ordinary Itinerary into An Unforgettable Experience

Planning the “ultimate” trip can be a challenge. It can drive you a little crazy. so how can you create an unforgettable experience?

I’m trying to plan an itinerary myself, and I see a lot of people commenting in groups and asking about the most minute details. And when someone asks for recommendations travellers tend to recommend the same tourist attractions over and over.

I get it. For those of us that suffer from anxiety, and others who may be travelling for the first time independently, the unknown can be scary and intimidating.

But here’s the thing. If you plan your itinerary to within an inch of its life, you lose any chance of having an authentic, unforgettable experience. And by staying on the tourist track, you miss the opportunity for those experiences to occur. That’s why I’m not a fan of tour groups (except my own of course!)

Chances are you will have the cookie cutter experience. Yes, it might be fun, and you might enjoy it, but ask yourself which you would prefer, a nice time or an unforgettable and unique experience?


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Don't have an ordinary time travelling when you could have an unforgettable experience #itinerary #travelexperience #unforgettabletravel #travelplanning


Don’t stress that you haven’t included everything in your itinerary. You never will; you need to accept it and move on. You may or may not return to this destination, but why not make the experience uniquely yours in the time you are there. It won’t matter that you didn’t see “everything”.

People will compare, “did you go here, did you see that?” How much nicer to be able to tell stories instead of comparing sites ticked off a list?

One of my favourite times in Arezzo, Italy was when it started to rain, and then hail, forcing us into a delightful café where we proceeded to order an antipasto platter and glasses of wine. We sat there for an hour or two, chatting, laughing, enjoying our impromptu snack while the hail pounded down outside, and we were cosy inside. I am not sad about not seeing the places on our list, but I am warmed by that memory when I think of Arezzo.


Creating the Perfect Itinerary

Guess what? You can’t! And don’t worry about it.

There’s no one standing at the airport saying, “You did it wrong!”

There is no wrong. There is no perfect. What you will have is your unforgettable trip, however, you did it.


Here’s what I do when planning:

  • Determine a time frame and approx. date (best to know the time of year)
  • Create a list of everything I want to do (no editing at this stage)
  • Add the most important ones to Google Maps
  • See where the larger groupings of those places are
  • Get rid of the rest (or save them for another trip)
  • Pick a base in each of those areas
  • Determine how many nights in each place
  • Create day trips to include the activities on your map
  • Keep it loose – plan only about 5 hours-worth of sightseeing a day

I may be a planner, but I also incorporate lots of free time in my itineraries. I allow plenty of time for each stop. That way if I get a recommendation from a local I can pursue it. Or if something catches my eye, I can explore.

Or maybe the weather will turn as it did in Arezzo, and I get to head indoors and experience something different or have a chat with locals.

If I am planning a road trip, I allow plenty of time in the day to stop along the way to explore a village or two. There will be plenty to see that you haven’t even heard of or thought significant. These often become your best moments because there were no expectations.

What I would find more difficult than not including everything in my itinerary would be to miss opportunities as they present themselves. If I don’t find things to fill the free time I can always add more from my original list into my day. Or spend some down time relaxing.


Don't have an ordinary time travelling when you could have an unforgettable experience #itinerary #travelexperience #unforgettabletravel #travelplanning


Plan Personal Experiences

The first time you plan a trip to a destination is the hardest. You have nothing to base it on except other people’s experiences and opinions.

Know yourself and what you would like. Travel does inspire you to try new things but if you are not a hiker at home, chances are you’re not going to turn into one and trek to a popular place for hikers somewhere else.

If you are into history, or love craft, or needlework or whatever else it is that you love, find those things. Check out local artisan stores or markets, find a historical society that can help you or embark on an epic foodie adventure.

As long as it resonates with you.

Facebook Groups

Read as much as you can from a variety of different people of all ages, backgrounds and interests. Facebook Groups are a wealth of information, and you also get a broader perspective.

I am a member of these two groups which are fantastic:

The Scottish Travel Society

Travelling to Italy

These groups have local members, so you are not only getting a traveller’s perspective but one from those that live there. Those recommendations have been invaluable for my planning process.

I used to read travel forums as part of my research; now I head to Facebook. Dedicated destination groups give you more insight than general travel groups so find the ones that suit you best.

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Change your Mindset

Remember, you can always come back. Don’t think just because you have been once you need to go somewhere else. If you loved it, return. See more, do more.

Too often people plan with the mindset to see it all because it will be the only time. You can’t see it all and you never will. Choose places that resonate with you, not ones from a list of the Top 10 things to do in (___).

Some years ago we went to Paris. People said we had to go up the Eiffel Tower and I should have known better. It was the biggest waste of three hours that I have ever spent. I vowed then not to do the things people say I “have to” do.

Don’t follow the worn-out tourist track because you think you “have to” see something. Follow your passion and see where the trail leads you. Ask yourself why you want to see something.

When we go to Scotland I want to visit Culloden Moor; Dan doesn’t. So he will do something else.


Embrace the Differences

Did you know the light in Europe is different from the light in Australia?

When we arrived in Italy on our last trip, it was around 10 am. On the bus heading to Cortona from Rome, I would have bet you a million dollars that it was 3 o’clock in the afternoon. The morning light was like our afternoon light in Australia.

It’s nice to notice things like that, to acknowledge the differences in the world.

It’s easy to want to see familiar things or compare to home. Try not to. Embrace the differences, try the different foods and try not to compare.

When I was young, and we travelled the differences were huge. Now technology has made the world smaller. We have many of the same things. So when you do see the differences, relish them.

That is what travel is all about.


Don't have an ordinary time travelling when you could have an unforgettable experience #itinerary #travelexperience #unforgettabletravel #travelplanning


Push the Limits of your Comfort Zone

Create moments that only you will have. A conversation, an interaction. Be open to new experiences, ones you might not find in the tourist sites and destinations.

You know those moments in time that sit in the recesses of your mind and are suddenly triggered by a song you hear quietly playing in the background? Or a scent that wafts past you on the breeze.

Those are the memories you want to create.

Get out of your comfort zone and experience travel every way you can. Step away from the well-worn path. It’s easier to stay on, I know. But it will not show you anything new, and your experience will be the same as the person before you and the one after.

I love staying in Airbnb’s because of the opportunity to talk to the owners and get their recommendations. A chance to chat.

When you are planning a trip, stop and think about the place, or attraction, that you “have” to see and think about the experience it may give you. Granted you may not know this until you have been but try and see beyond the “thing”.

Why do you want to see it? What will the experience give you apart from checking it off your list?

With shows like Outlander making destinations such as Scotland a travel hotspot I wonder what it is that draws people. Is it the film locations or Scotland itself? Is it the beauty they saw on the screen or the fact they can say I’ve been there.


Learn to Hold Back

I am planning a trip to Scotland, and it’s hard putting the itinerary together because I want to see and experience so many things. All the information I am reading is other people’s recommendations, and it takes time to find the bloggers I can relate to.

But I know from my own travel experiences that no matter what I include in our itinerary the days will lead us in a different direction. All it takes is a recommendation from your B&B host, or a note written in a visitor’s book, or a change of weather to prompt us to explore elsewhere.

Travel has taught me to be a planner, but travel has also taught me to plan for the unexpected. To see where it takes me. I am more than happy to let the plan slip and discover a place that will nestle its way into my mind as a precious memory, much like Cortona did. Unexpected, but oh so sweet.

Be Happy with your Decisions

Who deems a place worthy of visiting? Places once unheard of suddenly become popular. Once a destination becomes a “tourist attraction” it loses its appeal for me. Too crowded and no longer unique.

I wanted so badly to visit Iceland. But now, it seems to be “the” place to go. That’s why I would have to visit in winter, away from the crowds.

Find other places to visit. Trust me they are there. Jump off the tourist track explore elsewhere through the day and come later to the “must see” site when there are no crowds. Or rise with the sun and experience it then.

Travel and holidays are often in conflict with each other. Sleeping in versus an early morning unique experience.

Make it a travel experience as well as a holiday.

The choice is yours.

The good thing is that you do have the choice. Lots of them.


Cindy x

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Don't have an ordinary time travelling when you could have an unforgettable experience #itinerary #travelexperience #unforgettabletravel #travelplanning




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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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