If You Have To Do a Working Vacation, Here’s Why a Staycation Is the Way To Go

Photo: W+G Creative
No matter how you plan it, the main purpose of a vacation is relaxation. This might look like running around Paris and trying every croissant, or bungee jumping off a bridge in New Zealand, or lying on a beach in North Carolina—the point is it's a restorative experience where you're not obligated to do anything but have fun and enjoy a break from everyday life. But unfortunately, most American workers have a scant number of vacation days to use , so it’s easy and often necessary to let the lines that separate work and vacation blur—which is where the "working vacation" comes in.

Experts In This Article

Unfortunately, most experts are not super into the idea of working while you're on vacation. “The whole purpose of a vacation is to refresh and re-energize, and if we’re not able to do that it’s going to lead to burnout, so I definitely feel like it’s most helpful if we keep it separate,” explains Nicholette Leanza, LPCC-S, therapist at LifeStance Health. “When we’re fatigued because we’re always on, I just don’t think we’re the best we can be.” This can be especially acute if you’re going on vacation specifically to escape burnout and overwhelm. The only cure here, says Leanza, is to actually slow down. (And, you know, leave the work laptop behind.)

If you're splitting your mental energy and time between working and trying to relax in your off hours while on vacation, Leanza says it's probably going to mean you're only doing both half as well as you could be. Unless you're able to set strong mental boundaries, it can be tough to shift from work to play mode.

"The whole purpose of a vacation is to refresh and re-energize, and if we’re not able to do that it’s going to lead to burnout."—Nicholette Leanza, LPCC-S, therapist at Lifestance Health

An extra complicating factor about working on vacation is if the trip is a hush vacation, or an outing where you're seemingly available to work but really in a different location without telling your boss. Leanza says this practice can heighten stress rather than reduce it because of the element of deception. If your boss doesn't know you're in upstate New York but you're there trying to also enjoy some cider tasting and apple picking with your friends, you're probably not going to be able to fully lock in to either activity.

Those who do actually undertake working vacations tend to come back not feeling very refreshed, either. E-learning platform ELVTR  conducted a survey of 2,300 adults from both the United States and Canada earlier this year to examine work-life balance, and found that 68 percent of respondents admitted to working on vacation, and 46 percent said they struggled to unplug from work while on vacation. These numbers point to one conclusion: vacation for many workers isn't abundant or restful enough.

Is it ever possible to make a working vacation restful?

The unfortunate reality is that many workers may find themselves having to fit both work and play into their time off, even if it's generally not recommended. Sometimes mixing work and play is a means to make it possible to get away at all—if the choice is a working vacation or no vacation, the tradeoffs might feel worth it.

Roman Peskin, co-founder and CEO of ELVTR, says the term working vacation itself is a bit of a misnomer. "Vacation is a state of rest, so we're not really talking about a vacation here," he explains. "Instead, we're asking 'how can I experience what life has to offer without using those precious days off that we don't get too many of?'"

That's certainly how I've approached working vacation. I don't work when I'm actually off the clock, but I like to maximize my ability to work remotely with some warranted scenery changes with trips. I've done this with mixed results; a recent trip to New York saw me successfully bookend a lunch break spent surveying pieces at the Whitney Museum of American Art with working at a nearby coffee shop, but the same trip also included canceling dinner plans entirely and missing a friend in town to finish an assignment. It's made me wonder if it's truly possible to emerge from a working vacation feeling both well-rested and on the ball at work.

Although its relaxing benefits pale in comparison to a true, unplugged vacation, experts say a working vacation can be more manageable (and even somewhat relaxing) with some specific parameters in place.

1. Keep the time difference reasonable

One key to a working vacation is making the conditions for actually doing your work possible. It'll be easier to communicate with your team, for example, if you're within the same or a similar time zone. Peskin says it’s not necessary to have an exact match of your schedule with your team, but it’s helpful to have some overlap. Someone like me who lives in Washington, D.C. and travels to Miami, for example could easily take a working trip because these two cities are in the same time zone, provided you make sure to finish your work projects before shifting into vacation mode. Staying on top of your tasks becomes much tougher when you're dealing with a time difference of four or more hours—trying to line up Washington, D.C. and say, Bali, is a situation that'll be tougher than it's worth and likely warrants using PTO.

2. Don’t go somewhere you’ve never been, or need to explore

If part of your vacation involves seeing new sites, you want to make sure you have the time and flexibility to actually do so. Even if you do manage to get away to explore during the day, Peskin and Leanza both say you're likely not going to even enjoy what you're doing because you'll be worried about or occupied with work. Keep working vacations to places where you'll be able to have some new experiences, but your time won't be ruined if you don't hit everything on your list. It would be a big bummer to spend all of your first time in London inside your hotel room working and squeezing sightseeing and activities in only in the evening or early morning hours.

3. Set boundaries

"If you can't take time off [fully], protect the time by setting boundaries," says Leanza. And yes, that includes checking your email in off hours—make some of these boundaries digital, too. "Really try to say, 'When I'm at work in my hotel room I'm connected, but after work it's off and I'm with my family,'" she adds.

Similarly, when Peskin has to have a working vacation, he provides a couple hours to his team where they can reach him and then tells them when he's going to be unavailable. This streamlines communications and minimizes someone chasing someone else around for an assignment or project.

How it felt trying a working vacation as a staycation

In reporting this story—and thinking about my own working vacation experiences—I realized that I never came back from these trips relaxed or refreshed. I thought it was time to test out some of the experts' tips for myself and see if they resulted in a better experience.

Given the challenges outlined earlier about mixing work and play, I wondered if a staycation could be the ideal solution to the working vacation dilemma. The bar would be low in terms of having to accomplish a lot of sightseeing (since I would be in a familiar place already), so I wouldn't feel like I was wasting my time there by working. I could still fit in plenty of fun and relaxation after hours. I decided to test my theory during a three-week trip home to the Bay Area in August. Typically when I go home I match my East Coast team's 9 a.m. to 6 p.m. schedule by working from 6 a.m. to 3 p.m., which would leave plenty of time to hang out with my family and enjoy the Golden State afterword.

Conveniently, the 1 Hotel San Francisco reached out to me for two-night stay. Since I was already in the area, it seemed like a great opportunity to have a change of scenery in a place I called home. All that stood between me and the city in terms of travel logistics was an easy Caltrain ride. Plus, the hotel's focus on wellness and relaxation felt like the kind of low octave, inherently relaxing itinerary that would offset working.

I grew up running around San Francisco, so all the major sites like Alcatraz, the Golden Gate Bridge, Twin Peaks, and Golden Gate Park weren't must see's because I've already been many times. My main priority was just a change of scenery and seeing a couple new-to-me things that wouldn't require lots of logistical set up or time, like the new Sezane popup store on Fillmore Street and the Presidio Tunnel Tops. Bonus points for squeezing in some old favorites of mine around the city, and for getting my family out of the house. If I had time, I was open to something a bit more adventurous on Saturday, when I'd be off work and totally unplugged.


I rode the Caltrain up to the city around 4 p.m. after signing off for the day, and checked into the hotel. After freshening up and taking a quick nap in the soft bed, I headed out for shopping and some dinner on Fillmore Street. Typically I would've jumped on the MUNI bus or walked, but working all day put me in a time crunch, so I called a Lyft to the Byredo store, where I tested out some perfume that'd been sitting in my cart for ages.

After pressing my nose against the window of Fillmore Bakeshop to see if I could take home some treats (unfortunately, it was closed), I ventured to the Sezane pop-up, where I tried on a couple items I'd been coveting. Neither of these stores is available where I live, so it felt worth it to me to visit. I then treated myself to a solo dinner of kebabs and dips at Noosh, a Mediterranean spot recommended by a friend, before flopping back into the hotel bed in front of a Law and Order: Special Victims Unit marathon.

Because I didn't feel pressure to squeeze in major logistical undertakings, like seeing famous and crowded sites after work, I felt pretty relaxed and at ease. If I were visiting somewhere else, this pretty low-stakes evening might've felt like a waste in terms of maximizing my chances of seeing as much as possible. The only issue was that because I had work the next day, I kept jumping onto my computer to send emails to lighten my load for Friday before I finally stopped myself and went to sleep.


I started the morning as I do when I'm working from California, at 6 a.m.—getting out of the cloud-like bed was tougher than I'd like to admit. I worked from the hotel restaurant, Terrene, where I alternated handling a breakfast sandwich stuffed with avocado and eggs and my laptop. This was when temptation crept in; despite moving outside to work in the sun on the patio on the Embarcadero, all I could think about was how I'd rather switch places with the carefree group of friends having coffee and chatting next to me. My little brother and mom drove up shortly after noon, at which point I'd been working for six hours and already deep into my second major task of the of the day. Having my family there was comforting and lovely, but their arrival made me realize I wished I was off fully so I could spend more quality time with them.

Luckily my room was set up to be quite conducive to getting things done, and I wrapped up work on time after a busy day of writing and interviewing sources while my family relaxed. I was also able to fit in a walk along the Embarcadero and through the Ferry Building, where I sipped a coffee and watched the ferries come in and out of the dock as a break. I finally signed off 3 p.m. and checked into an appointment at the Bamford Wellness Spa for a one hour de-stress massage and sea salt tub soak before a dinner at the hotel’s restaurant with my family. After slamming the book on another workweek, the true vacation part of my staycation could begin.

The aromatic bath salt soak tub on the 1 Hotel San Francisco's rooftop terrace. Photo: Helen Carefoot

A massage might not feel so adventurous to others, but I'm someone who typically hates them. Surprisingly, this was my one itinerary activity that was outside of my comfort zone. I could feel the stress pouring out of my body as I shifted into weekend mode. By the time I entered the post-massage soaking tub, which was situated on a tranquil rooftop patio, I had shifted fully into offline mode. Lying in the warm water with my eyes closed, I sipped my tea and reflected on how this was the first time since coming to the city that I could feel the tension truly leave my shoulders and neck.

We capped the night at the restaurant, where we enjoyed a spread of appetizers, entrees, drinks (I had a particularly interesting cocktail made of ube and gin, fittingly named the "Ube Area"), and a just-sweet enough date cake with berries. While it was challenging juggling work with a family visit, I was so happy to have shared the dinner experience with my mom and brother. We fell asleep in the comfy beds watching Fraiser and What We Do In the Shadows, just as we typically do on the couch at home. I closed my eyes feeling totally at ease.


The next day we woke up early (considerably later than I'd been waking up though, luckily), and my mom and I strolled around the Ferry Plaza Farmer’s Market, a sprawling expanse of stalls filled with the juiciest heirloom tomatoes and fragrant flowers. I hadn't been here in years, and I loved seeing so many familiar vendors and stalls. We picked up some peaches and pastries to take home. Back across the street at the hotel, we grabbed my little brother and shared a sweet potato waffle with berries and protein smoothies for brunch before checking out and heading to the Presidio Tunnel Tops, a public park and picnic area built on top of the freeway tunnel that leads to the Golden Gate Bridge.

A waffle with berries.
The sweet potato waffle at the 1 Hotel San Francisco's restaurant, Terrene. Photo: Helen Carefoot

A stall of flowers at a farmers market.
A flower stall at the Ferry Plaza Farmer's Market. Photo: Helen Carefoot

It was a perfect San Francisco day: sunny with a light breeze, and so many people were out and about. Despite the bridge being hidden by fog, we sat in the picnic area and talked—a smile never left my face. We made a quick pit stop at Black Bird Bookstore and Cafe, a local gem in the Outer Sunset neighborhood just a couple blocks from the beach, before following the scenic Highway 280 home.

My goal for this stay was simply to have some fun and a change of my typical scenery, with experiencing new activities sprinkled on top as a bonus. Reflecting back, I fulfilled my hopes to get out of the house, have some fun, and try something new. Focusing my activities in one general geographic area—the immediate vicinity of the hotel, plus the Embarcadero and Fillmore Street—meant I didn't have to worry about covering a lot of ground, either.

Had I been somewhere I was any less familiar with or didn't visit often, though, I would've found this endeavor stressful. I often found my mind drifting back to work on the weekdays, which was frustrating. I can't help but think I would've been even more refreshed if I'd been able to unplug entirely to maximize my limited time in the city and with my family. (Luckily, I spent three whole weeks at home, so I had more time outside of these two days because they flew by.)

All in all, my working vacation was made much more manageable as a staycation, and it was certainly nice to get out of the house and experience all the hotel and the city had to offer. But I'll be sure to request some true unplugged OOO time when I need to fully rest and recharge.

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