Travel Itinerary: The Art of Unplanning

Posted by Ian in Itinerary, Tips

Eager Existence > Travel > Itinerary > Travel Itinerary: The Art of Unplanning

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A while back I wrote a guest post on keeping an open itinerary… but I discovered on ThornTree the argument is still alive and well. So, I am breathing life back into the argument of planning versus unplanning. I hope I can at least open up your eyes to an alternate perspective on travel planning.

My Argument

So my whole argument revolves around the idea of “going with the flow”; plan the basics, and give yourself plenty of flexibility.

Is your life planned out? …I hardly think so.

You might know what you’re doing this weekend, next week, and maybe even Christmas. But what about 5 years from now?

Even if you ARE a planner… how often do things go according to plan?

You can spend months planning out a trip, all the places you want to go. You can plan it down to the hour, but one missed connection, and you have to adapt and start to think on your feet.

Don’t even get me started on the “let down” feeling you get when things didn’t live up to your expectations.

Personally, I like the idea of not knowing who I will meet around the next corner, and where that interaction will take me.

I still believe in serendipity.

The evolving planning process: How I plan my trips

While you may not have a 5 year plan, everyone has vague plans (or is that dreams, or goals?) of what they want to see and do. Maybe it’s a bucket list written down on paper, or maybe its just things you are interested in, like adventure, beaches, festivals, culture, or food.

Let’s use me as an example.

I knew before I went to Europe what my vague plans were: Anzac Day at Gallipoli, Run with the Bulls, Ibiza, Oktoberfest, Greek Islands, Summer Camping, and a big Canoe Trip.

With the big events, it was easy enough to plan out. I knew that Anzac Day only happens once a year (like New Years Eve), Running of the Bulls and Oktoberfest only happen for a week or so, and Greek Islands and Camping …well, that would be during summertime.

I would love to say that is all the planning I did, but I would be lying. It was my first “big trip”. It was my first time travelling independently as an adult long-term, and as you can imagine, I was more than a little anxious, and afraid of the unknown.

So I planned my first 15 days by booking on a packaged tour. I figured 2 weeks at the start would be enough time for me to make some friends on tour, and get used to travelling by myself in a country where English was not widely spoken.

Beyond all that, I stuck to the 3 day rule for the most part. After all, who knows where I would be or who I would meet?

I was caught out a few times though, where I didn’t have plans for that day, and had no idea where I was sleeping that night. And as you can imagine, I was more than a little worried. A few times I had to sing “Don’t Worry, Be Happy” to myself, and hope that everything would turn out alright.

In general, I learnt to think a few days ahead, and fire off emails to hostels/couchsurfing hosts to reserve a bed. Any time I found myself in a great place, or amongst amazing people, I could easily alter my plans because they were only sorted 3 days in advance.

I hope in this post I have convinced some of you that you don’t need to have an entire 90 (or even 30) day itinerary planned out for yourself. Just get the first night or two booked, and your ticket there.

Leave the rest to chance. Go, enjoy yourself. You never know who you’ll meet.

And by living in the now, and feeling good about the current moment, you might just create a happy, enjoyable life now. Instead of “waiting for it to happen”. Focus on the present moment, how you can make the most of your circumstances. Enjoy every moment for what it is, on your journey, because when you get to the destination there will always be another dream or goal to aim for. – (paraphrasing) Alun Jones

It’s a nice concept isn’t it? Taking things as they come. Not planning too much out. Set a basic goal, a rough itinerary, and leave the rest to opportunity.