Tell me I’m not the only young working adult who feels the pinch of losing my freedom to travel whenever I want due to the limitations of annual leave. Rubbing salt to that, soaring flight prices post-pandemic means I need to become a master planner to snag those sweet deals and make the most of my holidays. Time to strategise around public holidays and long weekends like a pro!

There are 11 days of public holidays in 2025, six of which are long weekends. This means you can take five short trips without even using any of your annual leave. Sweet!

That said, not all of us have the privilege of 14 days of annual leave so take my recommendation as a guide for your own leave maximising strategy. Don’t fret if you don’t have that many days of annual leave; the good news is that according to Singapore’s Employment Act, in 2025, we are entitled to either one day off-in-lieu or an extra day’s salary in-lieu if a public holiday falls on a weekend.

Tips to make the most out of your annual leave

Who doesn’t love getting more for less? Finding the best way to really stretch your 2025 annual leave and take as many trips or breaks as possible is a start. You can also make the most of your annual leave by ensuring you don’t return to work feeling broke or like you never had a break!

Here are some ways to save money on your holidays and make work breaks feel “longer”:

1. Unwind and let your mind unbind

Resisting the urge to check your office emails or group chats on holiday can be harder than you think. However, ensuring you switch off work notifications can help you fully immerse in your holiday, so your vacation doesn’t feel “shorter” due to work distractions. This rule should apply even if your break doesn't involve hopping on a plane. Whether you want to mould clay in a pottery class, experiment in the kitchen, get your hands busy with woodwork or do absolutely nothing during your annual leave, the key to making every single moment rejuvenating is to really disconnect from work.

2. Activate airplane mode

Be the boss of your own "Hey Siri, switch on airplane mode" moment. The essence of taking annual leave is to break free from the chains of work, and the key to a seamless escape is smart pre-planning. By mapping out your tasks in advance, you ensure the work wheels keep turning even when you're off the grid. So, prepare like a pro, and let your time off truly be a break from the daily grind.

3. Take a red-eye flight

Unpopular opinion, but I do love taking a red-eye flight because I won’t have to spend half a day of my precious leave in the air, and I get to arrive early with more time to explore the country. Plus, airports tend to be quieter and immigration processes and checks move faster too since there are fewer passengers. Taking a red-eye flight also means cost savings since tickets are mostly cheaper, and you might even save on a night of accommodation.

4. Stretch your dollar

There are many ways you can stretch your dollar, one of which is using a credit card that offers you miles in return for your purchases. I mean, if you’re already going to be spending the cash, you might as well earn some miles too. If you look at it, hey! That’s like a “1-for-1” deal. Your ticket for your next trip, next-next trip or next-next-next trip might be free. You’re just one swipe away!

5. Snag the best travel deals

You might have heard of travel hacks such as purchasing your tickets on off-peak days or booking through an aggregator. However, there are ongoing travel deals such as Gotta Scoot Tuesdays with Scoot, and Singapore Airlines’ student promotion deals to take advantage of too. Airfare savings aside, some aggregators like Booking.com or Agoda offer free cancellation fees for accommodation bookings, allowing you to lock down the best prices. All these savings on bookings equals more travel spending money.

Travel fuss-free and with ease

Travelling should be fun and stress-free. After all, it is a chance to get a well-deserved break from work responsibilities (and life). However, accidents and unexpected events can happen when we’re overseas. The last thing you want to worry about is the medical expenses as a foreigner. This is why buying yourself peace of mind is encouraged. During my recent trip to Japan, I was stuck in Okayama for two days due to the closure of the Shinkansen because of a typhoon. I had to cancel all my existing bookings and change my travel plans. Thankfully, I was well supported by my insurance claim agent, and the process to file for my travel insurance claims was straightforward. I even got my payout shortly after I returned! TALK ABOUT EFFICIENCY!

So, if you’re looking to travel to multiple destinations in 2025 with my annual leave hack, consider looking for an annual travel insurance plan such as Singlife Travel Insurance which offers comprehensive coverage including things such as trip cancellation and curtailment for any reason*. You get additional bonus discounts if you’re a MINDEF/MHA/POGIS insured members. WHAT A STEAL! Check out Singlife Travel Insurance page for the latest travel insurance deals.   

Get ready to unleash the ultimate office battle – declare your fight and secure those dates before your colleague beats you to it. It's game on!

^{*Only available for Travel Plus and Prestige plan.}