Annual Leave Optimizer (2026 & 2027)
Turn a handful of leave days into the longest possible breaks. Enter your leave balance and this planner maps Singapore’s 2026 & 2027 public holidays against weekends to show the fewest days you need to take for the most days off. Everything runs in your browser — no sign-up.
What is a long-weekend “leave hack”?
Singapore has 11 public holidays a year. When one falls next to a weekend, a single day of annual leave can bridge them into a four- or five-day break — and a cluster like Chinese New Year can turn one leave day into five days off. This optimizer does that maths for every 2026 & 2027 holiday at once, then builds the highest-value plan that fits your leave balance.
calendar_monthPick your year
2026 or 2027
edit_calendarEnter your leave balance
How many days you have
auto_awesomeGet your best breaks
Auto-built — tweak any of them
Year
Your 2026 plan
Add a break to start your plan
across 0 breaks · 14 leave days left
Best value in 2026: Chinese New Year — take 1 day (Mon 16 Feb) for 5 days off (Sat 14 – Wed 18 Feb).
Best 2026 breaks
Take 1 day → 4 days off
starBest valueThu 1 – Sun 4 Jan
You take leave on Fri 2 Jan.
Take 1 day → 5 days off
starBest valueSat 14 – Wed 18 Feb
You take leave on Mon 16 Feb.
Take 1 day → 3 days off
Sat 21 – Mon 23 Mar
You take leave on Mon 23 Mar.
Take 1 day → 4 days off
Fri 3 – Mon 6 Apr
You take leave on Mon 6 Apr.
Take 1 day → 4 days off
Fri 1 – Mon 4 May
You take leave on Mon 4 May.
Take 2 days → 5 days off
Sat 23 – Wed 27 May
You take leave on Mon 25 May, Tue 26 May.
Take 1 day → 4 days off
Sat 30 May – Tue 2 Jun
You take leave on Tue 2 Jun.
Take 1 day → 4 days off
Sat 8 – Tue 11 Aug
You take leave on Tue 11 Aug.
Take 1 day → 4 days off
Sat 7 – Tue 10 Nov
You take leave on Tue 10 Nov.
Take 1 day → 4 days off
Fri 25 – Mon 28 Dec
You take leave on Mon 28 Dec.
My 2026 Annual Leave Plan
0 leave days → 0 days off · smartcalculator.sg
Singapore public holidays 2026
| Holiday | Date | Day off |
|---|---|---|
| New Year's Day | Thu 1 Jan | Thu 1 Jan |
| Chinese New Year | Tue 17 Feb | Tue 17 Feb |
| Chinese New Year | Wed 18 Feb | Wed 18 Feb |
| Hari Raya Puasa(estimate) | Sat 21 Mar | Sat 21 Mar |
| Good Friday | Fri 3 Apr | Fri 3 Apr |
| Labour Day | Fri 1 May | Fri 1 May |
| Hari Raya Haji(estimate) | Wed 27 May | Wed 27 May |
| Vesak Day | Sun 31 May | Mon 1 Junin lieu |
| National Day | Sun 9 Aug | Mon 10 Augin lieu |
| Deepavali | Sun 8 Nov | Mon 9 Novin lieu |
| Christmas Day | Fri 25 Dec | Fri 25 Dec |
Source: Ministry of Manpower (MOM). Gazetted public holidays for 2026. Hari Raya Puasa and Hari Raya Haji dates are subject to confirmation. Assumes a 5-day work week (Saturday and Sunday off). For reference only — confirm leave with your employer.
How the optimizer works
1. Map the calendar
We mark every weekend and public holiday in 2026 & 2027 as a day off, including the Monday in-lieu days for Sunday holidays.
2. Find the bridges
For each holiday, we work out the fewest leave days that connect it to the nearest weekends — the classic long-weekend “hack”.
3. Rank by value
Breaks are ranked by days off per leave day. We auto-select the best ones that fit your balance — you can adjust any of them.
Tips to stretch your leave
Bridge to the weekend: a holiday on a Tuesday or Thursday only needs one leave day (the Monday or Friday) to make a four-day weekend.
Chase the clusters: Chinese New Year and the late-May Vesak/Hari Raya Haji window sit close to weekends, so a day or two of leave stretches a long way.
Mind the in-lieu Mondays: when a holiday falls on a Sunday the day off moves to the Monday — the planner already uses the actual day off.
Book early: the best-value dates (the ones marked “Best value”) are the first to fill up with colleagues, so request them ahead of time.
Frequently asked questions
How many public holidays does Singapore have in 2026 and 2027?expand_more
Singapore has 11 gazetted public holidays in 2026: New Year's Day, two days of Chinese New Year, Hari Raya Puasa, Good Friday, Labour Day, Hari Raya Haji, Vesak Day, National Day, Deepavali and Christmas Day. 2027 also has 11, but MOM has not gazetted them yet, so the planner shows estimated dates for 2027. Where a holiday falls on a Sunday, the following Monday is a public holiday.
How does the annual leave optimizer work?expand_more
The tool maps Singapore's public holidays against weekends, then finds "bridges" — the small number of leave days that connect a holiday to the nearest weekends into one long break. It ranks every opportunity by value (days off per leave day) and auto-selects the best ones that fit your leave balance.
Are the 2027 dates official?expand_more
Not yet. MOM typically gazettes the next year's public holidays around April. For 2027 the fixed dates — New Year, Chinese New Year (substitute Monday 8 Feb for the Sunday), Good Friday, Labour Day, National Day and Christmas — are reliable, but Hari Raya Puasa, Hari Raya Haji, Vesak Day and Deepavali are estimates that may shift by a day. The tool labels 2027 as estimated and we update it once MOM confirms.
Does it account for the Monday in-lieu day for Sunday holidays?expand_more
Yes. When a public holiday falls on a Sunday, the following Monday is gazetted as the public holiday (for example Vesak Day, National Day and Deepavali in 2026, and the second day of Chinese New Year in 2027). The planner uses the actual day off — the substitute Monday — when finding your best breaks.
Can I use this if I work a 5.5 or 6-day week?expand_more
The planner assumes a 5-day work week with Saturdays and Sundays off, which fits most office jobs in Singapore. If you work Saturdays or a 6-day week, your weekends differ, so treat the suggested breaks as a guide and adjust for the days you actually work.
Does it plan for 2027 as well?expand_more
Yes — switch to the 2027 tab. Note that MOM has not gazetted 2027 public holidays yet, so 2027 is shown as estimates: the fixed dates (New Year, Chinese New Year, Good Friday, Labour Day, National Day, Christmas) are reliable, while Hari Raya Puasa, Hari Raya Haji, Vesak Day and Deepavali may shift by a day until confirmed.
Is my data saved?expand_more
No. The tool runs entirely in your browser — nothing is uploaded and there is no sign-up. It assumes a 5-day work week (Saturday and Sunday off); always confirm leave with your employer.