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Trip Planning 101 – How much should you plan for?

When you are planning for your next holiday, have you ever wondered whether you had done enough prep work and made all the necessary bookings? Or have you worried about overdoing it and not giving yourself any room or free time to explore and enjoy? The question I always find myself asking when I’m floundering in research or uncertainty, is…

Is there a right way to plan a trip?

The answer to that quite simply, is of course not. You need to do what feels right for you, no matter what other people tell you. Many people decide to skip the hassle of all this and just go on a group tour, and that’s fine as well – you do save yourself the headaches of logistics and wondering if you’ve made the best deal – but this is for the independent travellers, or those who usually leave the work to their friends and are now embarking on their own solo trips, only to realise that there’s a lot more work involved than they had thought.

So here are some of my own experiences and tips on how you can plan your own independent trips without wanting to tear all your hair out.

Identify your most important trip goal

Whether or not you’ve actually decided on your destination already, the one thing you need to ask yourself is ‘what exactly do I want out of this trip?‘. The answer can range from anything as simple as ‘rest and relaxation’ and ‘to see new things’, or to more specific things like ‘eat the best Michelin starred food’ or ‘take a picture on top of that famous rock’.

Once you’ve identified your trip goal, it helps you justify and make decisions for the rest of your trip quite easily. It’s easy to rationalise skipping a visit to the Mona Lisa despite your FOMO when your main goal in Paris is to hit the top 3 restaurants as rated by locals. This all sounds like common sense, but sometimes I do need a bit of a reminder when I’m feeling a bit overwhelmed by sheer variety, or feel like I’m being pressured into doing something I don’t want to do.

Penang Street Art Armenian Rat Me

Lots of people love Penang for its food and culture – I unapologetically love its street art and in 2016, spent a long weekend there hunting down the most interesting street art spots without a care in the world for its awesome food. I really enjoyed myself though I doubt anyone of my friends would have!

Trip planning can be a bit of a black hole sometimes that sucks you in – what starts out as a simple query on things to do spirals into hours or recommendations and reviews and conflicting advice. I’ve been there and before I know it, I have 20 tabs open telling me everything I wanted and didn’t want to know about visiting the Great Wall of China.

It’s fine if you have multiple goals but be sure to rank them in order of priority. Life is a lot easier when you don’t have to agonize over which awesome thing to cut out from your trip.

Read more about how I planned my Career Break travels, where I had to figure out my travels for stints as long as 4-5 months instead of just 2 weeks.

My Trip Planning Style

I’m a big fan of independent travel – it’s a habit passed down from my Dad who never liked to be on a group tour. Our family holidays were full of car rentals, map reading and sleeping at random guesthouses that we found along the way. Now that I’ve started my own solo travels and am solely responsible for my trip’s itinerary, it got me thinking about how I plan my own travels.

I used to be more of a detailed planner. I would have done the research before my trip, know where to go, made all the major bookings like of tours if necessary. With limited time, my goal was to be as efficient and see as much as I could in that short amount of time, hence the need for detailed planning.

Career Break Budget Google Sheet

I’m more of a detailed documenter than a planner these days – read about how I detailed my 15 month Career Break travels

Gradually as I became more comfortable being on my own, I started to loosen up a little. I’ve realised that I do like some spontaneity and surprises, and having everything so well mapped out left little room for that. What I tend to do now is still fix certain things like my flights and my accommodation because I still can’t travel with peace of mind not knowing whether I have a bed for the night, but leaving my itinerary open to suggestions from people around me.

I used to scoff at people who could recite facts and figures at me even before we got there, to me it took the mystery and wonder of experiencing the place for the first time, but on the other hand, sometimes I didn’t fully grasp the significance of what I was looking at until I looked it up later online, and then I wished I’d known it before I went.

What type of a trip planner are you – do you research it or wing it? Are you that studious researcher who has every move detailed in a spreadsheet, movement planned to the minute? Or are you that free spirit who changes your mind on a whim, turns up as you feel like and barely even worries about where you are going to sleep for the night?

Terrie Kelley

Thursday 3rd of May 2012

I like to get an overview picture of where I'm travelling. I started traveling to far off places when my kids were in grade school, and I found that children's books about countries had the type of info I wanted: how most people lived, national foods and past times, common religions and languages. That helps me put everything in context. If I want more info about something, I can do more research.

I research a place enough to know certain things that I want to do. And the rest of the trip I play by ear. I want the holiday to be fun, not a race to accomplish a check list.


Thursday 10th of May 2012

Children's books - that's an interesting way to research for a country! never tried that, but you do make a good point =)

It's a bit of a balance between maximizing your limited time in that space and just wandering around the city... takes some work to get the best of both worlds really!