couple relaxing on resort island

Children like candy. Adults practically WORSHIP long weekends.

You know, the ones that last longer than two days?

So, for all you hardworking people out there, you’ll be happy to know that 2023 is absolutely filled with these blissful breaks, and if you’re prudent with your annual leave, you’ll be able to stretch some of them out for much, much longer.

Now, it goes without saying that you (probably) shouldn’t waste these golden opportunities mooching about watching TV. Rather, you might find these extended breaks much more fulfilling by journeying beyond the confines of our little red dot. As such, we’ve done up a “cheat sheet” of sorts to help you out.


Three-day long weekend escapes from Singapore


·        Labour Day (Monday, 1st May)

·        Duration: 3 days (no annual leave required)


Labour Day 2023 is your quintessential 3-day long weekend, though you’re naturally free to extend it at your own discretion. This might not seem like much on paper, but believe us, the feeling is totally different once you’ve made it to the Friday before.

With that in mind, three days is still enough for you to spend a nice weekend away from Singapore. Sure, you won’t have time to go anywhere too fancy, so visiting a neighbouring resort island like Batam is definitely in the cards.

You’ll be able to travel there by taking a ferry from Tanah Merah Ferry Terminal (TMFT) or Harbourfront Ferry Terminal, and you can spend the next two days golfing at the island’s various 18-hole courses, relaxing with a good massage or simply basking in the sun enjoying the downtime. It’s simple, but sometimes this is just what the doctor ordered, and don’t worry about your Internet connection either – here’s how you can stay connected for cheap, even on a prepaid card

scuba diving with fishes

For four (or five!) days of fun in the sun


·        Good Friday (Friday, 7 April)

·        Hari Raya Puasa (Saturday, 22 April)

·        Vesak Day (Saturday, 3 June)

·        Hari Raya Haji (Thursday, 29 June)

·        Deepavali (Sunday, 12 Nov)

·        Duration: 4 days (using 1 day of annual leave)


Now, you might be wondering why all of these have been grouped together, and that’s because most of 2023’s long weekends happen to be four-day breaks.

By using one day of annual leave each (that’s five in total!), you’ll be able to enjoy a whopping TWELVE days out of the office across these five public holidays, excluding the actual weekends themselves. That’s an impressive number in and of itself, not to mention that four-day windows open up loads of new getaway options too.

Given our location on the map, the most feasible options (unfortunately) remain in Southeast Asia, but don’t sell them short. If you don’t mind the great outdoors, Cebu in The Philippines offers great options for that, and it’s not too far from our little red dot.

For example, you can go swimming alongside sardines in Moalboal, or head out for some canyoneering at Kawasan Falls. Accomplished divers will also appreciate the opportunities, as the waters here offer the chance to get up close and personal with friendly whale sharks. 

elephant statue in thailand

·        Chinese New Year (Sunday, 22 Jan to Monday, 23 Jan)

·        Duration: 5 days (using 1 day of annual leave)


If you’re not celebrating the Year of the Rabbit, the upcoming Chinese New Year break is arguably the single most value-for-annual-leave opportunity you’ll be getting this year.

Specifically, you’ll be able to enjoy a whopping five days out of office using just one day of annual leave.

Notably, this gives you more than enough time for a short trip out of Singapore, and Bangkok, Thailand is always a great pick for some well-deserved R&R. Chow down on traditional “boat noodles” at the Damnoen Saduak Floating Market, scope out the majestic Ayutthaya Temples, or say hi to the elephants at Pattaya Ethical Elephant Sanctuary. Thailand has a good mix of urban and countryside offerings that are truly refreshing for “city mice” like us, so feel free to cut loose – among other things, we know we’d like to ride on one of those elephants!

These aren’t “long weekends” anymore (in a good way)


·        Honorable Mention: National Day (Wednesday, 9 August)

·        Duration: 5-9 days (using up to four days of annual leave)


Don’t worry, there’s no typo. You can potentially get NINE whole days off to do whatever, whenever, provided you’re willing to pony up four days of annual leave in August.

With National Day 2023 sitting smack dab in the middle of the week, we thought we’d drop this one in as an honourable mention. By taking leave on the remaining four days that week, you can plan for much more than an average weekend away from Singapore. In other words, you’ll have enough time to visit European destinations like Oslo, Norway.

Case (or rather, city) in point, temperatures at this time of year average around 18 degrees Celsius at noontime, so you can presumably leave most of the bulky winterwear at home. Plus, starting off in Oslo also allows easy access to numerous attractions. These include the Oslofjord Cruise to the Bygdøy Peninsula, where you can explore the Viking Ship Museum, as well as the famed Scenic Bergen Railway, which offers a picturesque view of some of the most beautiful landscapes in the world. Make sure to bring a powerbank too, because you’ll definitely want pictures for keeps.

friends enjoying winter holiday

·        Christmas + New Year’s Day (25 Dec and 1 Jan 2024)

·        Duration: 10 or 11 days (using 4 or 5 days of annual leave respectively)


Last but not least, we arrive at the most glorious of long weekends – the year-end holiday season. Christmas is always a week off from New Year’s (obviously), which means that with some dedicated saving, you’ll be able to plan for a ten or even eleven-day break starting 22 Dec (Friday).

Incidentally, that’s why we’ve also saved the most unique holiday destination for last. Granted, it’s also in Europe, but this special venue is only open for business between December and April each year. Why? Because it melts.

Freshly constructed out of snow and ice each year, the legendary Icehotel in Jukkasjärvi, Sweden promises a once-in-a-lifetime experience. For our foodie friends, the hotel hosts a restaurant that serves a 12-course tasting menu inspired by the local Sami culture (think elk meat and smoked reindeer!), and there are guided tours for you to try all sorts of unique cuisines.

Meanwhile, the artsy types might want to check out the in-house art gallery as well as the themed suites, which are redesigned and crafted yearly. With a little luck, visitors can even head out to see the aurora borealis (otherwise known as The Northern Lights) on clear nights, and these are nothing if not gorgeous.


Bon voyage!


Regardless of where you decide to travel this year, you’ll definitely want to take LOTS of pictures for the “gram”, and as such we can’t stress how important it is to have reliable roaming.

With all that in mind, we hope this list has given you a couple of vacation ideas to work with, and perhaps it can even serve as an inspiration for the year ahead!