Free tool
Annual Leave Optimizer
Tell it how many leave days you have. It finds the exact days to book around the public holidays and weekends for the longest possible breaks.
The plan
Turn 8 leave days into 24 days off
Across 4 breaks in 2026, using public holidays and weekends.
Thu, 1 Jan to Sun, 4 Jan
4 days off for 1 leave day
Book 1 day (2 Jan).
Sat, 14 Feb to Wed, 18 Feb
5 days off for 1 leave day
Book 1 day (16 Feb).
Sat, 28 Mar to Sun, 5 Apr
9 days off for 4 leave days
Book 4 days (30 Mar, 31 Mar, 1 Apr, 2 Apr).
Wed, 27 May to Mon, 1 Jun
6 days off for 2 leave days
Book 2 days (28 May, 29 May).
Uses gazetted public holidays (from data.gov.sg) plus weekends. Confirm dates with your employer before booking.
How it works
Public holidays that land next to a weekend already give you a long weekend for free. The trick is the gap days in between: booking one or two of them can bridge a public holiday to the nearest weekend and turn two days off into four or five. This tool checks every bridge in the year and picks the ones that give you the most days off for the fewest leave days, without overlapping.
This page assumes you already know how many days you have. If you do not, the annual leave calculator works out the statutory minimum from your start date, using the Ministry of Manpower formula.
Common questions
How does the Singapore leave optimizer work?
Enter how many annual leave days you have. The tool checks every gap between Singapore public holidays and weekends and picks the bridge days that give you the most consecutive days off for the fewest leave days, without overlapping.
How can I maximise my annual leave in Singapore?
Book leave on the working days between a public holiday and the nearest weekend. Bridging one or two gap days can turn a single public holiday into a four- or five-day break; this tool finds every such bridge for the year automatically.
Is the leave optimizer free?
Yes. It runs in your browser using the official gazetted public-holiday dates from data.gov.sg, and is completely free to use.