If you work a job with limited paid time off, you have to be strategic about using it, whether you want to have more short breaks throughout the year or have an extended trip planned that requires banking days and using them all at once.
We’ve written before about how to maximize annual vacation days by stacking them up against weekends as well as federal and state holidays so your time off feels like more than it is. The Stretch My Time Off tool can actually do that for you based on the exact number of PTO days you have—whether you get a paltry two weeks or want to take several dozen days with an unlimited policy—as well as the national holidays in your country (and state-specific holidays if you’re in the U.S.). The calendar gives you a visual of when your maximized vacation will fall, and you can even set it for a future year if you want to really plan ahead.
Even if you don’t use the tool’s complete recommended schedule, it’s helpful to see suggestions for extending weekends as well as where you could assign a vacation day or two during a holiday drought (in that long stretch between President’s Day in February and Memorial Day in May, for example).
As a self-employed worker, 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 anticipated PTO.
How to use Stretch My Time Off to plan vacations
The Stretch My Time Off interface is simple: Select your country (and state if in the U.S.), enter the number of days off, and choose the year you want to view. The tool will automatically block national (and state) holidays and arrange your PTO around them. You can also hide specific holidays or change your “weekends”—if you work Saturday/Sunday and have Monday/Tuesday off, for example—to further customize the suggestions.
One limitation is that it won’t show you more than one configuration of vacation time by rearranging your days off, but with the full calendar view, it’s easy to see alternatives. For example, Stretch My Time Off placed four vacation days around Veteran’s Day (in November) for a full week off, but instead of having two weeks in November (with Thanksgiving week off), those days could just as easily be used the week of July 4th or Memorial Day or for extending any other four-day week into a nine-day trip.
