The Simple Secret to Travel Planning

As I’ve shared throughout this retirement series, one of the things I’m most looking forward to is having the freedom to travel more. Not because I want to be constantly on the move, but because I love discovering new places, creating memories and having the time to truly enjoy the experience. If you’re new here you might enjoy the first article in this series.

Of course, everyone approaches travel differently.

Are you a travel planner?

I have heard a lot of opinions on this over the years.

Some people love to go with the flow. They arrive somewhere new, wander out the door and simply see where the day takes them.

“We’ll just walk around and see what happens.”

Doesn’t that sound wonderfully carefree?

It fills me with dread.

I wish I were joking!!!!

Tony and I have done a fair bit of travelling over the years, both overseas and within Australia, and I can tell you without hesitation that the trips where we have been a little more organised are the trips I have enjoyed the most.

Now, if you’re firmly in the no planning, just see what happens camp, hear me out.

Because when I say I plan our holidays, I don’t mean I have every fifteen minutes entered into a colour-coded spreadsheet.

I’m a planner.

I’m not a monster.

Travel Planning Doesn’t Have to Mean a Rigid Itinerary

I think this is where travel planning gets a bad name.

People hear the word itinerary and imagine being marched past a beautiful little café because the schedule says you need to be standing in front of a museum at precisely 10.15 am.

That is definitely not how we travel.

I would never plan every minute of every day. For me, one of the great joys of travelling is discovering a place as you go.

It’s turning down a street because it looks beautiful.

Stopping for a coffee somewhere you hadn’t heard of.

Finding a shop you want to wander through or a garden you didn’t know existed.

Sometimes we see something on our way to somewhere else and make a mental note to come back. Other times, we simply stop and admire the beauty of the area before moving on.

You need space for those moments.

But I have discovered that I also need a starting point.

“The World Is Your Oyster” Is Not Helpful Advice to Me

You know the saying, the world is your oyster?

Some people hear that and feel excited by all the possibilities.

I hear it and think:

Which way do we go? What do we see? Where do we start? Are we wasting the day? Have we missed something wonderful in the opposite direction?

Too many choices can quickly become overwhelming for me.

I know this about myself now.

When I’m faced with an enormous number of options, particularly somewhere unfamiliar, I can become stuck trying to make the best decision.

And holidays are far too precious to spend an hour sitting in a hotel room asking each other, “What do you want to do?”

“I don’t mind. What do you want to do?”

“I’m happy with anything.”

Forty-five minutes later, we’re still sitting there.

No, thank you.

Why Planning Our Holidays Helps Me Enjoy Them More

One of the reasons I plan our holidays is very simply to avoid overwhelm.

If you experience anxiety, you may understand how quickly too many decisions can take the joy out of something you were looking forward to.

For me, planning removes some of those decisions before we even leave home.

We wake up in the morning and already have a general idea of where we’re heading.

I don’t have to work too hard to start the day.

And that makes an enormous difference to me.

There’s no standing on a footpath in a new city scrolling through our phones trying to decide which of the 147 recommended attractions we should visit.

We simply start.

Once we’ve started, I’m quite happy to see where the day takes us.

It’s the starting I need help with.

My One Thing a Day Travel Planning Rule

When I’m planning a trip, I generally choose at least one thing to focus on each day.

That’s it.

It might be a private tour when we’ve first arrived somewhere new. I particularly love doing this because it gives us an introduction to the area and often helps us discover places we’d like to return to later in the trip.

It might be a major attraction we really don’t want to miss.

Or it could be as simple as a lunch spot we’ve been wanting to try.

That one thing becomes the anchor for our day.

We know where we’re heading, and then we let the rest of the day unfold around it.

Tony and I usually walk as much as we possibly can when we’re travelling. So if we have somewhere to be for lunch, we’ll often walk there and see what we discover along the way.

And we always discover something.

A beautiful building.

A tiny shop.

A street we want to explore.

A view we hadn’t expected.

A place to stop for coffee.

The plan doesn’t stop us from discovering a new place.

The plan simply gets us out the door.

And I think that’s the difference.

I Also Plan Where We Might Eat

I do something similar with food.

Before we travel, I usually make a list of places we might like to eat.

Again, this isn’t a rigid schedule.

Tuesday at 7.05 pm: pasta.

Wednesday at 6.42 pm: seafood.

That’s not happening.

It’s simply a list of options.

Because after a full day of walking and exploring, decision fatigue is very real.

There comes a point in the day when Tony and I are tired, hungry and completely incapable of answering the question, “Where should we eat?”

Having a small list of places I’ve already looked at makes life so much easier.

We can choose something nearby, see if we can get a table and go.

It removes another decision, at exactly the time when I have the least energy to make one.\

Travel Planning Is Even More Helpful When Travelling With Others

I think planning becomes even more important when you’re travelling with other people.

Everyone has different things they want to see and do.

One person loves museums.

Someone else wants to shop.

Another person has one particular landmark they’ve dreamed about seeing for years.

Trying to uncover all of that while you’re already on holiday can be difficult.

Before we leave, I think it’s much easier to talk about the things that are particularly important to each person.

What is the one thing you would be disappointed to come home without seeing or doing?

Once you know those things, you can make sure they’re incorporated into the trip.

It doesn’t mean everyone has to do everything together.

It simply means the important things aren’t accidentally missed because nobody spoke up until the last day.

A little planning before you leave can prevent a lot of frustration once you’re there.

Planning Gives Me More Freedom, Not Less

I know that probably sounds completely backwards to a spontaneous traveller.

But planning actually makes me feel freer.

I’ve already done the thinking.

I’ve narrowed down some of the choices.

I’ve made sure we won’t miss the things that really matter to us.

So when we arrive, I can relax.

I don’t feel the need to squeeze absolutely everything into the trip because I know we’ve made space for our priorities.

And when something unexpected comes along, we can change the plan.

We’ve done it plenty of times.

A plan is not a legally binding contract.

If we’re tired, we rest.

If we find somewhere we love, we stay longer.

If the weather changes, we change direction.

If we wake up and simply don’t feel like doing what we’d planned, we don’t.

The plan is there to help us.

We are not there to serve the plan.

Maybe You Don’t Need to Plan the Whole Holiday

If you’ve always thought of yourself as someone who hates travel planning, perhaps the answer isn’t a detailed itinerary.

Maybe you just need a starting point.

Choose one thing for each day.

Make a short list of places you’d like to eat.

Ask everyone travelling with you what they really don’t want to miss.

Then leave plenty of room in between.

Room to wander.

Room to discover.

Room to sit somewhere beautiful with a coffee and watch the world go by.

For me, that’s the perfect balance.

A little bit of planning to remove the overwhelm and plenty of space for life to happen around it.

So, tell me—are you a travel planner or do you prefer to see where the day takes you?

And if you’re firmly in the go with the flow camp, have I changed your mind even a little?

Because I’m still not leaving the hotel without at least a vague idea of which direction we’re walking.

Some things about me are simply not going to change. If you want more travel planning tips you will find a free Travel Planning Guide here.