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Life & fun · January 15, 2018

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Tool to help workers get the longest possible vacations

Get maximum vacation days by taking into account public holidays using the lowest amount of actual vacation days.

Tool to help workers get the longest possible vacations launched on January 15, 2018 with 10 votes, #1,061 of 3,021 launches that month and more than 75% of that year's launches. The site was still online in September 2026, 8 years on.

Visit stretchyourannualleave.com ↗Alternatives

In plain words

This tool helps workers and employers maximize vacation time by strategically planning days off around public holidays. It eliminates manual spreadsheets and complex calculations by automatically identifying optimal booking periods that extend time away from work while conserving actual vacation days. Designed for both employees seeking longer breaks and managers handling time-off requests, it simplifies leave management and reduces administrative coordination through email and paperwork.

written from the facts on this page · September 2026

From the sources

Get maximum time off by booking your vacations around public holidays. Manage employee time-off the easy way, without the spreadsheets, the crazy calculations or the never ending emailfrom stretchyourannualleave.com

Does a similar job

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  • Stretch Your Annual Leave2018 · stretchyourannualleave.com · ▲75

    Tool to help workers get the longest possible vacations

  • VacayWiser2024 · vacaywiser.com · ▲216

    Find the best days for vacation

  • Stretch My Time Off – An Algorithm to Optimize Your Vacation Days2024 · stretchmytimeoff.com · ▲358

    Hey HN! I built StretchMyTimeOff as a quick experiment using Cursor (Anysphere's AI code editor) and GPT-4o to see how far AI could go in building a simple, functional site. What it does: The site helps you get the most out of your vacation by suggesting optimal days to take off around national holidays, maximizing long breaks with minimal vacation days, anywhere in the world and for any calendar year. It's an idea I've had for a while, and building the algorithm with GPT was a fun challenge. Any feedback or ideas I'm all ears :)

  • Off Day App2025 · offday.app · ▲5

    Maximize time off with minimum leave days

  • Stretch My Time Off2024 · stretchmytimeoff.com · ▲10

    Optimize your vacation days with AI-powered planning

  • Vacation Maximizer – Maximize PTO by taking days off around holidays2025 · vacation-maximizer.com · ▲6

    Hey! In my last job I was constantly wondering when it would be best to take days off so I could enjoy the most days off in a row, so I made this tool! It tries to schedule PTO around holidays so that you get the most consecutive time off while spending as few days as possible. You can set some constraints, customize the holidays and define mandatory vacation days (in case your company mandates them). If you try for 2025, you should see results for the rest of the year. If there are unscheduled days, it's because there isn't a particularly good period to take them off. (I should make this…

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