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.
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
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.
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