travel planning: our first backpacking trip

For years, I’ve been terrified at the thought of travelling. It’s quite embarrassing to admit, but just taking a flight or bus by myself is enough to give me a mild panic attack and make me hyperventilate some. Needless to say, I’m obviously a far cry from being any travel guru.

As scared as I am however, I can’t deny that there is a certain allure in getting out of Singapore. So, come this December, I decided to be bold for once and go on a 14-day backpacking trip, my first ever, with my bff, Hilda (check out her beautiful blog @! And so, from December 27 to January 10, we’ll be heading to Bangkok, Ko Samui, Penang and Ipoh before finally returning to sunny Singapore. (Hilda is actually going away for much longer, for several days to Cambodia before meeting me in Bangkok, so do keep a lookout on her blog for posts on Phnom Penh and Siem Reap!) It is VERY outside my comfort zone, but I’m also so thrilled that it’s going to happen!

Over the past week or so, we’ve been meeting up almost daily to plan our itineraries, book tickets and accommodation and settle our finances. I’ve learned more about travel planning than I ever thought possible, especially since I’ve never planned so much for a trip in my life! Considering how everyone goes about the travel planning process differently and the sheer amount of work our planning entailed, I thought this warranted a blog post all on its own.

Here’s how we planned our short two-week getaway!

1. Pick a destination


“Did you know that in Taman Negara, there’s an adventure trekking trail which includes an overnight stay in a cave? You can actually count the stars when you look up at the night sky.”

We winded up having to cross Taman Negara off our list due to the monsoon season making trekking difficult, but it was our ‘adventurous dream’ of sleeping in a cave (filled with bat shit, I’m sure), which really kick started our EOY trip. After hiking in Taman Negara, we could go white water rafting in Ipoh, sight-seeing in Penang, partying in Ko Samui and shopping in Bangkok, we thought. Or Hilda could always fit Cambodia in and we could do the rest in reverse. And it would still be great!

2. Decide how long you want to go for

Once we decided where we were going, we had to decide how long we wanted to stay in each destination, which wasn’t hard at all. We knew there were certain places we wanted to visit on certain dates, such as Ko Samui during New Year’s – can anybody say BEACH PARTYYYY!!! Also, since I start school again in the second week of January, our end dates were pretty much fixed.

3. Research how much it’s going to cost


It’s very easy to estimate a ballpark figure when changing money, and simply change more later on if necessary. Since we were going to be travelling on a shoestring budget however (sad poor student here), we didn’t have that luxury. So, we made a budget sheet which detailed our cash on hand and estimated expenses by day and by destination. This really helped us decide how much money to change too.

4. Book your transportation

After having factored in our transportation costs, which by the way were probably the most expensive item on our budget sheet, we then quickly booked our plane, train and bus tickets. If anything, I learned that booking early really is paramount to not only save money but to actually get a better transport option. Unfortunately, I learned that the hard way, so I suppose from Bangkok from Ko Samui, instead of chilling in comfortable overnight sleepers (the rail tickets were all sold out), we’ll be bouncing around on a jerky bus and probably get really bad neck aches. Time to invest in a neck cushion, seriously.

5. Book your accommodation

While we were at it, we decided to book our accommodation too. Especially since we’re travelling during the peak Christmas-New Year period, we decided to play it safe and book most of our accommodation in advance, at least till Koh Samui. Here’s hoping the hostels will have free laundry!

6. Plan your itinerary


When you’ve four destinations to cover in just 14 days, itinerary planning is paramount! After all, nobody wants to come all the way to a new country only to find that they’ve arrived on a day when certain activities are unavailable. We planned our itinerary by the day and hour, with 30-minute intervals, and tried to pack it up as full as possible. It’s always best to be prudent and plan more rather than less – after all, you never know which activity you might want to drop or change at the last minute.

7. Pack

Finally, it’s time to pack! For a medium length trip such as this, I started packing a few days in advance (aka around now), just so I’ve enough time to buy some things that I don’t yet have and will probably need – a portable charger and travel pouch for instance.


8. Buy travel insurance

Some may think that buying travel insurance is a huge waste of moolah, but I never dare travel without it – unless of course I’m headed for a day trip to Johor Bahru or a routine family trip to Cameron Highlands (which for my family happens nearly twice a year). It may seem like an unnecessary fee, but the coverage for possible travel inconveniences such as loss of money and personal belongings and various medical expenses sure make it all worthwhile. Better to be safe than sorry!


There’s a whole lot of things you can do to plan an (ideally) smooth, seamless trip, though I guess we’ll only find out just how seamless it’ll be once we’re on it. Of course, some may say that such in-depth planning in a sense detracts from the fun of travel, of fortunate happenstance and pleasant surprise. I don’t deny that at all. In fact, on our previous trips together, Hilda and I didn’t plan a thing (except our accommodation), and those turned out great! So I suppose the degree of planning really depends on the trip – whether you’re on a tight schedule, spending sometimes just a single day in some places, or whether you’ve a flexible budget in terms of both time and money. Either way, remain open-minded and positive about your travels, and you’ll have a great time! Have fun 🙂


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