A long break rarely comes from a single holiday. It comes from the pattern around it: a public holiday next to a weekend, a one-day gap, another weekend. Leave Optimizer treats public holidays and weekends as anchors and your annual leave as bridges between them. Tell it your country, how many leave days you have and any extra company days off, and it finds the combinations that turn the fewest leave days into the longest unbroken stretches of time off.
The scoring is deliberately transparent: each bridge is rated by the continuous days off it produces divided by the leave days it costs. A bridge that spends two leave days to build a nine-day break scores 4.5; a bridge that spends five days for the same nine scores 1.8. The optimizer then picks a set of bridges that do not overlap and fit inside your leave budget, so the plan it hands you is one you can actually take.
Three strategies cover the three ways people actually plan. “Longest single break” finds the one mega-break for a big trip. “Spread evenly” puts the best bridge in each quarter first and then fills the remaining budget optimally, so your year has several breaks instead of one. “All opportunities” lists every bridge ranked by score, for people who want to pick their own. Every plan comes with a twelve-month calendar, a one-click leave list and a .ics file you can import into Google or Outlook calendars.
How to plan your 2027 leave
- Pick your country. The tool covers ten countries for 2027: the United States, the United Kingdom (England & Wales), Germany, France, Japan, South Korea, Australia, Canada (federal), Singapore and Hong Kong.
- Enter how many annual leave days you have to spend — the optimizer will never recommend more than this budget.
- Set your weekend: Saturday–Sunday by default, or Friday–Saturday if that matches your work week.
- Click any working day on the calendar to add it as a company day off — useful for office closures and team shutdowns. Click again to remove it.
- Choose a strategy: the longest single break, an even spread across the year, or the full ranked list of opportunities.
- Take the plan: copy the leave list to send to your manager, or download the .ics file and import the leave days into your calendar.
How the optimizer works, honestly
The method is small enough to check by hand, and the data behind it is pinned to official calendars — so a surprising recommendation can always be traced back to a real holiday.
| Aspect | What happens | Good to know |
|---|---|---|
| Anchors | Public holidays plus weekends form fixed blocks of time off | Company days you add join the anchors |
| Bridges | Each working-day gap between two anchors is one bridge candidate | A bridge that spans two adjacent gaps counts as one longer break |
| Scoring | Each bridge is rated by continuous days off divided by leave days used | Higher is better: more break per day spent |
| Selection | A weighted-interval search picks non-overlapping bridges within your budget | Two recommendations never claim the same leave day twice |
| Company days | Days you click on the calendar count as free days off | They can extend a break or replace a leave day |
| Data | 2027 national holidays, checked against official sources | Regional holidays are excluded; see the notes below |
One honest limitation: a recommendation is only as good as the holiday data, and regional holidays are deliberately out of scope for this version. If your state or province adds a holiday, add it as a company day and the optimizer will use it.
Frequently asked questions
How does the optimizer find long breaks?
It treats public holidays and weekends as anchors — days you already have off — and looks at the working-day gaps between them. Filling a gap with leave days joins the anchors on both sides into one continuous break. Each such bridge is scored by the continuous days off it produces divided by the leave days it costs, and a weighted-interval search picks the set of non-overlapping bridges that fits your leave budget.
What do the three strategies do?
“Longest single break” returns the single biggest break available, for one big trip. “Spread evenly” takes the best bridge in each quarter first and then fills the remaining budget with the optimal set, so your year has several breaks instead of one. “All opportunities” lists every bridge ranked by score, so you can pick your own combination.
Which countries are covered? What about China?
Version 1 covers ten countries for 2027: the United States, the United Kingdom (England & Wales), Germany, France, Japan, South Korea, Australia, Canada (federal), Singapore and Hong Kong. China will join once the State Council publishes the 2027 holiday schedule — the 2027 arrangement was not published yet when this tool was built, and guessing at Chinese make-up workdays would produce wrong recommendations, so China is left out rather than approximated.
Why do some holidays seem to disappear in Germany and France?
Because Germany and France have no substitute-day rule: a public holiday that falls on a weekend is simply lost, with no weekday given in return. In 2027 that costs Germany three holidays (1 May, 3 October and 26 December) and France four (1 May, 8 May, 15 August and 25 December). The optimizer counts only the weekday anchors that actually exist.
What do the Australia, Canada and United Kingdom notes mean?
Australia’s national set excludes Anzac Day, because its observed day differs by state: in 2027 Anzac Day falls on Sunday 25 April and is observed on Monday 26 April in most states except Victoria, South Australia and Tasmania — if that applies to you, add 26 April as a company day. Canada uses the federal set of ten holidays, which applies to federally regulated workers; provinces differ on Remembrance Day and Boxing Day. The United Kingdom uses the England & Wales set; Scotland and Northern Ireland differ.
How do I use the plan once I have it?
Two ways. “Copy leave list” puts a plain-text summary — breaks, dates and the efficiency line, such as “5 days of leave → 18 days off” — on your clipboard for a message to your manager. “Download .ics” gives you a calendar file with one all-day event per leave day, which imports directly into Google Calendar or Outlook. Your inputs never leave your browser in either case.
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