5 Steps to Stretching Your Annual Leave for Travel


So a friend, Jac, recently shared this click bait hope-inducing article on “4 ways Singaporeans can get more time off work”. Both of us couldn’t identify with it so I thought I’d write something a little more relevant to us wanderlust driven Gen Y folks.

Honestly, I think my tips are damn basic, but since people tend to ask tell me, “Wah, you travel so much hor! So good!” I guess, that’s reason enough to share how I manage my leave balances to travel.

1. Decide what brings you most joy when travelling

Everyone has limitations, so work on what maximizes the enjoyment of travel for you

I think the silliest thing to do when it comes to utilizing your leave is to not enjoy the time you take a break from work to the fullest. I would assume that since you’re reading this that you definitely do enjoy travelling. However, do you know what makes you happiest when you head abroad?

Figure out what is it that YOU want from your travel experience.

  • Do you enjoy short but more frequent breaks to “get away” from the mundane environment OR longer holidays once or twice a year to truly immerse yourself in the experience of a new country?
  • On a sliding scale with urban city environment and adventurous outdoors on either end, how would you shift the knob to show your preference of activities and locales when travelling?
  • Are you someone who wants new experiences, no matter how straining, OR someone who just wants to relax and chill and experience something you’re used to in a new way?

Ask yourself these questions and be careful when you answer; Always answer truthfully of what speaks to you. Even if what speaks to you is, “I want to take beautiful photos of myself in a different country” or “I want to check the main tourist attractions off my travel the world list”. You don’t have to be ashamed of what others think of it. It’s what brings YOU most joy. So just shove all that noise about what is the “right” way to travel out the door and do what pleases you most.

Finding fulfillment and satisfaction in travel basically comes down to this: Are you happy with what you’ve made happen? Once you get this and own your travel decisions, you’ll realise it doesn’t matter how many days of leave you’ve got, its all about how you decide to spend it.

2. Learn to Use Half Day or Full Day Leave to Your Advantage

Figure out when a half day or full day of leave pays off the most when stacking with weekends

Travelling takes time. It’s a given. Most people I know find it more appealing to take a full day leave before the weekend just to fly over to their holiday destination in comfort or sometimes so that they can disembark and start exploring earlier in the day as opposed to a “wasted day”. Here’s the deal, depending on your (and your companions) travel preferences and plans, you don’t always need to take a full day of leave.

Apply for one day of leave but split it into two half day leaves

This is great for when flights don’t take more than 5 hours and you still want to reach by evening and not too late at night to enjoy dinner and nightlife (e.g. night markets, bars, after-hours activities).

I will use this tactic to fly to places I already frequently travel to or do not find much difficulty in visiting (both in terms of flight and accommodation pricing), each time to discover a different part of it. I don’t think its necessary for me to cram exploration of the “entire destination” in a single trip. The beauty about affordable travel is, you can save up to visit the same place again. The following destinations are under 5 hours (all stated flight times are approximate) and suitable for this arrangement:

  • Krabi/Phuket (1 hour 48 minutes)
  • Surabaya (2 hours 11 minutes)
  • Bali (2 hours 35 minutes)
  • Hanoi (3 hours 24 minutes)
  • Hong Kong (4 hours)
  • Taiwan (4 hours 48 minutes)

Take half day leave on your date of departure which allows you to leave work by lunch time, bring your luggage with you to work (hopefully you’re not an over packer since this works for weekend trips), check-in online, catch your flight before 3pm. For your return flight, take half a day leave on date of arrival back in Singapore and catch a morning flight that gets you back to work by lunch time.

Apply for full day leave when there is a possibility of a long weekend

For holidays which require a bit more spend on air tickets and accommodation, more time for time-consuming and physically strenuous activities, or just because I want to unwind more, I look to possible long weekends.

These are for travel plans to destinations which aren’t suited for “quick getaways”. Whether I want to exhaust my full fourteen days at a go to enjoy two to three weeks away from work (with strategic leave taking into account public holidays) wandering a number of cities and going for an adventurous road trips, or travel to somewhere else to live like a local for a week, that’s the time I whip out my full day leaves and choose to apply for them.

For now, my longest trips are to Australia and Japan where I travel to multiple cities. It’s my choice whether I want to do a touch and go kind of holiday or a slower dedicated trip to one location only.

3. Decide on Your Big Ticket Trips Each Year

Work out the dates for your big trips so you can allocate the rest of your annual leave

I find it most effective when I decide on a big ticket trip destination for the year and how long I’d like to be there for and work towards saving for and planning that.

I then set aside the remaining annual leave days for short holiday trips that require maximum of two days of annual leave and I leave them for spontaneous decisions with friends or when there’s a great airline deal.

Once I have exhausted my leave days for the year or when I just need a breather from day-to-day humdrum, I go away for the weekend, leaving on Friday evening after work and coming back on Sunday night.

4. Find Out Where You Can Spontaneously Travel to Without Taking Leave

When wanderlust bites, you don’t have to pick exotic places to have new experiences

I think sometimes we just can’t travel too far away because we have that many days of annual leave and we’re saving it for something else, but it doesn’t mean you can’t travel. People tend to think that certain places are uninspiring and boring, but there are plenty of places you can travel to that is great for a day or two away from home and doesn’t require deductions to your leave balance. It’s about finding those places and researching to see if there is anything you can do or find there that caters to what you want in a holiday.

Whether you end up choosing Penang, Melaka, or the same old, same old, beach holiday location like Phuket, it really doesn’t matter. Have you ever considered that the way to have new experiences is just to look at holidays differently?

Boredom is a state of mind. If you’re a person who likes to check off the places you’ve visited, why not check off different attractions, activities and experiences within the same destination instead? Is it really a waste of money to fly back to the same state if you get to try something else?

When I was younger, I would visit Bangkok to shop till I drop. But these days, that has become something I can do without (because I shop often enough now that it is no longer a novelty). I travel to Bangkok to look out for cultural spots, new cafes, suss out cool Thai designers, meet and make new friends and the list goes on. I have a new focus with each visit to a country I am becoming more and more familiar with.

Also, I’ve been to the same destination twice or thrice and each time with a different group of travel companions. The experience is then different as the group dynamics change and activities then take on a different flavour.

5. Save Enough to Allow You Choices

When you have limited annual leave, you need to put aside more savings to travel

Here is a dose of reality for you. If you have limited days of annual leave, you’ll most likely need to build most of your travel dates around “peak periods”. The long weekends and public holidays are hot dates for every Singaporean. Travelling on “off peak periods” is cheaper but also means you’ll probably need to dig into your dwindling leave balance for the same number of days.

As accommodation and flight prices become pricier during your preferred travel dates falling on these “peak periods”, your best bet is to give yourself the option to choose it when it comes.

For me, I would rather travel than buy a branded wallet or bag. I’d rather not shop on holiday and just spend on food, drinks and transportation. At the end of the day it is what I VALUE and what I find CREATES VALUE for me.


In conclusion…

I’m just going to say though, that no matter how much annual leave I have, it will never be “enough” because I’d always want more. I’ll put it out there that I have fourteen days of annual leave a year with an additional one day of leave that can be cleared on my birthday month (a privilege given to me by my company and not a benefit). That said, its not something I spend time grousing about. I don’t think I have “too little”. I deal with whatever I’ve got and I stretch it as much as possible so that I’d be satisfied when I look back in the year and see how I’ve managed to travel.

This year I’ve been to Bangkok (twice), Melaka, Shanghai, Phuket, Hong Kong, Perth and, my last trip for the year will be to, Ho Chi Minh and Vung Tau. That’s eight trips in a year or two trips every quarter. This is a personal choice I made and I don’t regret it.

Just today, as I was sharing this article on Facebook titled “The Tail End” by Tim Urban, which illustrates perfectly the finite nature of life, another friend of mine commented:

Screen Shot 2015-12-15 at 12.57.12 AM

I remember one time when someone asked me if $30,000 was a lot of money. I said no, not really. Then he said, well, that’s also the number of days an average man has and that I’ve spent around a third of it already. 🙁

That is what life is, isn’t it? Make your choices and set your priorities and then just go for it.

Photography: Cheryl Tay


4 Responses to 5 Steps to Stretching Your Annual Leave for Travel

  1. Karen Ashley Ng December 15, 2015 at 1:58 pm #

    Great tips! I’m already starting on my 2016 travel plans.

    • Carrie December 15, 2015 at 5:38 pm #

      Thanks Karen! 🙂 I’m still deciding on my big trip for 2016, but yes, now is a good time to start planning before life just sweeps us all away.

  2. hazel December 15, 2015 at 5:24 pm #

    I think your working place is so ideal for travelling whole year round! So convenient especially when you bring your luggage along.hahaha!

    • Carrie December 15, 2015 at 5:27 pm #

      Hahaha. You said it! True.

      Then again, I carry tonnes of stuff with me even when I don’t travel. Just heading to work and then to events I can be carrying one hand big bag, one hand camera bag and a laptop. I think its just something I am accustomed to!

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