Updated
August 12, 2026
6 min read
Looking to plan ahead for your long weekends in 2027? Here's a quick guide to maximising long weekends so you can squeeze in more short trips and family time!
2027 is a great year for long weekends. Five of Singapore's public holidays already border a weekend, giving everyone a long weekend without touching their leave balance at all. Add a bit of strategic planning and negotiating on top of that, and you could turn every single one of the year's 11 public holiday occasions into an extended break – that's up to 10 long weekends!
Status: Confirmed Long Weekend
Why not take an extended New Year's break to focus on setting your goals and targets for the year ahead? If your company isn't already providing an extra day or two off during this period, using four leave days right at the end of 2026 can get you ten full days of rest to refocus and recharge. And we know some companies might just take the initiative to grant those days off anyway. Take the time you need to start the year with intention!
The Details:
PH on Friday
Requires Leave?: No
Long Weekend Dates: 1 - 3 Jan
Make It Longer: 25 Dec '26 - 3 Jan '27 (4 Leave Days in 2026 + Christmas Friday PH in 2026)
Status: Confirmed Long Weekend
It's the Year of the Goat... or Sheep, or Ram! Take a short break for your Lunar New Year visiting needs, especially for those who have to travel to visit relatives. For those who aren't celebrating, you could consider a vacation up to nine days, using three days of leave and one off-in-lieu, or just four days of leave – still a discount from the typical five. And if you decide to stay put at the workplace, we hope it won't be 'meh'. Have a goat-ed time!
The Details:
PH on Saturday and Sunday
Requires Leave?: No (1 holiday-in-lieu on Monday for Sunday PH)
Dates: 6 - 8 Feb, 6 - 9 Feb (1 off-in-lieu *if applicable)
Make It Longer: 6 - 14 Feb (4 leave days OR 3 leave days + 1 off-in-lieu *if applicable)
Status: DIY Long Weekend
Hari Raya Puasa falls on a Wednesday in 2027, so it won't give you an automatic long weekend — but a couple of well-placed leave days on either side will do the trick nicely, whether you're spending the day visiting or just taking a breather.
The Details:
PH on Wednesday
Requires Leave?: Yes, add 2 leave days
Possible Long Weekend Dates: 10 - 14 Mar (2 Leave Days), 6 - 10 Mar (2 Leave Days)
Make It Longer: 6 - 14 Mar (4 Leave Days)
Status: Confirmed Long Weekend
Good Friday is that one long weekend we've all come to expect, since this one's definitely on a Friday! Whatever your plans are, whether it's a spiritual or relaxing weekend, a day off from work means it's going to be a good Friday for sure.
The Details:
PH on Friday
Requires Leave?: No
Dates: 26 - 28 Mar
Status: DIY or company mandated Long Weekend
Labour Day is slated to be on a Saturday in 2027, which means for most people on a 5-day work week, an off-in-lieu (not everyone though, please check!). This is where your company policy takes precedence on how you can spend your off-in-lieu. If you can choose, or your company dictates the next working day as an off day, then this is your opportunity for a long weekend to kick off the merry month of May. After all your hard "labour" at work, May-be treat yourself to a few days away to relax!
The Details:
PH on Saturday
Requires Leave?: No, 1 off-in-lieu day *if applicable
Dates: 1 - 3 May (1 off-in-lieu Day *if applicable)
Status: Confirmed Long Weekend
Hari Raya Haji falls on a Monday in 2027, giving you an automatic long weekend. But here's the real headline: it lands just three days before Vesak Day (see #7 below)! Take two leave days in between and you can bridge both holidays into one 6-day break — or add a third leave day and stretch it into a 9-day May getaway.
The Details:
PH on Monday
Requires Leave?: No
Long Weekend Dates: 15 - 17 May
Make It Longer: 15 - 20 May (2 Leave Days: 18-19 May + Vesak Day PH) for 6 days, or 15 - 23 May (3 Leave Days + Vesak Day PH) for 9 days
Status: DIY Long Weekend
Vesak Day falls on a Thursday, so a single leave day on Friday gets you a four-day weekend for quiet reflection and mindfulness, or a quick getaway, or why not both at a retreat or resort nearby. And as mentioned above, it sits close enough to Hari Raya Haji that the two can be combined into one of the best vacation-ready stretches of the year.
The Details:
PH on Thursday
Requires Leave?: Yes, add 1 leave day
Dates: 20 - 23 May (1 Leave Day)
Make It Longer: Combine with Hari Raya Haji (#6) for up to a 9-day break using just 3 leave days
Combining the Hari Raya Haji and Vesak Day public holidays, with just 3 leave days, can earn you a 9-day break from work. Whatever you decide to do with this info, the earlier you realise this the better!
Status: Confirmed Long Weekend
National Day falls on a Monday in 2027, so you get a long weekend to celebrate the nation's birthday without spending any leave. Wear your red and white with pride, and enjoy the extra day to recharge before the final stretch of the year.
The Details:
PH on Monday
Requires Leave?: No
Dates: 7 - 9 Aug
Status: DIY Long Weekend
Deepavali falls on a Thursday in 2027. Take a single leave day on Friday and you've got yourself a four-day weekend — plenty of time to prepare for the festivities, visit family, or simply enjoy the extended break.
The Details:
PH on Thursday
Requires Leave?: Yes, add 1 leave day
Dates: 28 - 31 Oct (1 Leave Day)
Status: DIY or company mandated Long Weekend
It's the end of the year, and everyone's favourite time to get out of the office and enjoy the holidays. Christmas Day is slated to be on a Saturday in 2027, which means for many people on a 5-day work week, an off-in-lieu (not everyone, please check!). This is where your company policy dictates how you can spend your off-in-lieu. If you have a choice, or your company sets the next working day as an off day, then this is your opportunity for a long weekend to close out the year in style. Want to make the most of the year-end lull? A few more leave days on top gets you a full week off, nicely into 2028. We'll leave you to do the math, but we're dreaming up our holiday plans already!
The Details:
PH on Saturday
Requires Leave?: No, 1 off-in-lieu day *if applicable
Dates: 25 - 27 Dec (1 Off-in-lieu Day *if applicable)
Bonus: 25 Dec '27 - 2 Jan '28 (5 Leave Days: 27-31 Dec OR 4 Leave Days + 1 off-in-lieu *if applicable) for a 9-day break, or even including 3 Jan '28 for a 10-day break using the off-in-lieu *if applicable for the Saturday PH on 1 Jan 2028.
If you play your cards right, you'd need just 4 leave days and 2 off-in-lieu days to enjoy a long weekend for every public holiday occasion in 2027. That's not including the tempting 9-day stretch in May, where you'd trade in just 3 leave days.
You could in fact allocate your leave days to take an extended break once a month, or plan a long vacation while still enjoying long weekends throughout the year. Just saying.
We know that corporate demands mean you probably won't be able to take all your leave days whenever you'd like, but we're putting this out early for you to make your plans and 'chope' your days off. Let's get that break!
Looking for more ways to engage your employees and coworkers? Reach us here.
*Please note this is just a guide and certain dates are still subject to change as of the time of writing - please confirm the actual dates on your own and refer to your company's leave allowances and policies while you're planning!
