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    Are Remote Working Vacations Worth It?

    Published/Updated: Nov 24, 2025 · Erica Ho · 2 minute read

    Here's a huge disclaimer: The remote working vacation is not a vacation.

    There's three kind of trips: the vacation, the business trip and the remote working vacation these days. If anything, the remote working vacation is a full work week in a different place besides your house (or office).

    Prepared to work, and be prepared to be tired at the end of the day. Prepared to want to do nothing.

    Though the spirit may be willing, the last thing on your mind may be exploring, all the while paying the tune of $105 per night for lodging.

    That's a remote working vacation.

    That is not to say remote working vacations are worth it-they've got their pros and cons; everyone has different abilities to manage their time differently-but there are things to consider when deciding to stay in a place for a week or even realizing that the traditional three-day weekend might be a better option (which it can be).

    If you're going to commit, or test drive out a remote working vacation, here are a couple of pointers to actually enjoy one.

    Otherwise you are paying for five nights for nothing. Is that worth it?

    Breaking the costs down

    If you're considering doing it, it might be worth it to look at the actual numbers before deciding on a remote working vacation or a longer weekend.

    These are just some sample costs that we ran for four days and eight days in Mexico City, respectively. It should give a sense of how much more you are paying for the privilege of working while on vacation. 😅

    Mostly, we looked the two biggest categories, which was airfare and lodging.

    (It didn't make sense to account for the cost of incidentals, activities, and food, since those things are so variable.)

    Here's what we found:

    May 20-23 May 20-28
    Airfare $509 $479
    Hotel $135 $485
    Total $644 $964

    Though actual costs will vary depending on season, airfare, and destination, the four-day weekend clocks in at 33.2% cheaper, saving $320 versus from staying the full week.

    Now the next thing to consider, is to consider how much you will actually be working.

    Mondays are hellish no matter the place

    • Save

    FOMO is real. (Dennis Sylvester Hurd / Flickr)

    Sure, Mondays are cheaper to travel on, but nobody likes Mondays, whether that is at the office, at home, or in Mexico.

    Recently, a friend spent five days in the Hamptons-Friday to Tuesday-and didn't even bother to walk 2 minutes to the private beach on the last night, a Monday night.

    That's how tiring and stressful Mondays can be. Think hard before booking that day.

    Don't lie to yourself.

    Consider working half days

    In our opinion, this is really the best way to enjoy a remote working vacation.

    It even justifies the cost of lodging!

    If you can swing the time zone, consider going to a place where you can work super early and then skedaddle by noon. That way, there is still the rest of the day to play.

    (It's better than working late or through dinner time! Trust us on this one.)

    Request two (or three) days off the week

    This way, if you are staying for a week, there are four (or five) full days off to enjoy the destination. Sure it requires taking time off, but don't you deserve an actual vacation?

    • Save

    Go nuts. (Dennis Sylvester Hurd / Flickr)

    It's a good compromise, if working half days aren't possible.

    Trust us, there's a lot less anxiety on this one than trying to juggle it all.

    Or... try to squeeze in sightseeing during lunch.

    How reliable is your cell phone reception, and how much attention do you need to play to Slack?

    This is slightly playing with 🔥 in our opinion, because girl gotta make a dime to maintain her lifestyle and I'm sure you do too.

    • 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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