I Used This Free Tool to Maximize My Annual PTO
If you work in a job with limited paid time off, you have to be strategic about how you use it, whether you want to have more short breaks throughout the year or plan a long trip that requires banking days and using them all at once.
We’ve previously written about how to maximize your annual leave days by combining them with weekends and federal and state holidays to make your free time seem longer than it actually is. The Stretch My Vacation tool can actually do this for you, based on the exact number of vacation days you have—whether you get a measly two weeks or want to take dozens of days with an unlimited policy—as well as national holidays in your country (and state-specific holidays if you’re in the US). The calendar gives you an idea of when your maximum vacation time will be, and you can even set it for next year if you really want to plan ahead.
Even if you don’t use the tool’s full recommended schedule, it’s helpful to look at weekend extension suggestions, as well as places where you could schedule a day or two off during the holiday drought (like that long gap between President’s Day in February and Memorial Day in May).
As a self-employed person, I don’t have a set number of days off each year, but I used this tool to identify options for a week-long trip in 2026 based on my partner’s expected time off from work.
How to Use Stretch My Time Off to Plan Your Vacation
The Stretch My Time Off interface is simple: select your country (and state if in the US), enter the number of days off, and select the year you want to view. The tool will automatically block national (and state) holidays and configure PTO around them. You can also hide certain holidays or change “weekends” (for example, if you work Saturday/Sunday and have Monday/Tuesday off) to further customize your offerings.
One limitation is that it won’t show you more than one vacation time configuration by changing holidays , but with the full calendar view it’s easy to see the alternatives. For example, Stretch My Time Off placed four vacation days around Veterans Day (in November) for a full week off, but instead of two weeks in November (with Thanksgiving off), those days could just as easily be used during the week of July 4th or Memorial Day, or to extend any other four-day week into a nine-day trip.