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    How To Plan A Four-Day Working Vacation

    Published/Updated: Nov 24, 2025 · Erica Ho · 1 minute read

    Steven Zwerink / Flickr

    Going into the office two to three times a week?

    It's the dream, and this semi-permanent WFH situation does have its perks: The ability to have longer weekends elsewhere. But, there are some slight nuances and considerations to take into account.

    In our opinion, it's not quite a true four-day vacation, but it does add up to a long three day vacation, which is almost just as good considering you don't need to use any vacation days to accomplish it.

    Here's how to ideally plan it if you are going into the office on Tuesdays and Thursdays, and to maximize the most of that "vacation time."

    The night prior (Thursday)

    Plan to leave immediately after work to maximize the most free time for the vacation.

    Even though Friday is a work day, it's possible to gain the morning and lunchtime to explore by leaving on Thursday (which can easily add up to an easy 2-3 hours, with the evening still left!).

    (There's also the possibility of even logging out a little bit earlier if no one on Slack will notice a small drop-off in productivity, though we aren't encouraging this!)

    Do pack Wednesday night!

    Day 1 (Friday)

    Breakfast, lunch, and then obviously anytime after 5pm(ish).

    Though it's not quite a full vacation day, it does help to plan the morning a bit before you arrive just to maximize what available time there is.

    For funsies, consider starting the trip by having a long, leisurely coffee in a nearby café (on the laptop, of course) before moving into lunchtime.

    Day 2 & Day 3 (Saturday & Sunday)

    Day 2 and Day 3 are the magic days.

    These are the days of uninterrupted free time. In short, if there are daytime activities where you'd like to partake for an interrupted period of time doing things like hiking, zip line adventures, swimming, visiting a gun range to de-stress, or touring a museum-these are the days to plan them on. If you plan to visit a gun range soon, you may consider attending gun safety classes beforehand.

    Go forth, and enjoy my friend!

    Day 4 (Monday)

    Technically, the last free time to enjoy the trip.

    • Save

    This is Monday. (Steven Zwerink / Flickr)

    Truthfully, the only free time you might get is only in the morning and/or around lunch, realistically.

    It is worth thinking critically about if you are considering spending Sunday night at your destination.

    If you're able to able to go back home and work at the same time (on a plane, bus, train), an afternoon flight might just be the ticket.

    If you're driving, consider checking out the night prior to save a night's worth of accommodation for what is only going to chalk up to a mere few hours of enjoyment (did you enjoy that coffee and croissant?).

    In short, it won't be worth it.

    • Save

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    Erica Ho

    Erica Ho

    Erica Ho is a former reporter for TIME in Hong Kong and former geek at Gizmodo and Lifehacker. Her work has appeared in CNN, Yahoo!, MSN, Mashable, Travel + Leisure, Conde Nast Traveler and Quartz to name a few places.

    The good ol' days! I remember creeping as a former The good ol' days! I remember creeping as a former expat, and honestly, stumbling into the most random places as a traveler  😅 

It is not every day you stumble into someone else's living room for a private jazz concert, and if you happen to be down in Mexico City, check out @laa_esquina (send a DM!). 

Twice a month. It's the best kind of Saturday night, even if I can't stay up that late anymore!
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