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Work · February 23, 2026

Annually

Turn your annual leave into smart mini-vacations

What it does

Annually is an AI powered time off optimizer that not only tells you when to take leave but also where to go. It analyzes public holidays, leave balance, seasonality, travel demand patterns and timing efficiency to generate optimized vacation plans with destination suggestions for each leave window. Instead of manually hunting for bridge days and then researching trips, Annually turns a few days off into smarter and better timed getaways. Smarter timing. Better destinations. Maximum time off.

Does a similar job

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  • SM
    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 :)

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  • SS

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