Working while on vacation?

A stretch of time not thinking about work is the core value of vacation, but you could experience a lot of a city while working nearly full-time. I'd make "remote working time" distinct from "vacation", but while separate, maybe consecutive. So, 2 weeks of working from Madrid. Then log out for a week of real, disconnected vacation in, say, Andalucia.

I’ve done it. It’s not quite “vacation” but it’s a great way to experience a place. At least in my situation I couldn’t move to different towns or do a more typical trip - getting a place in one city with good WiFi and staying put for weeks is different from going to a different town and exploring every 3-4 days. So key is picking a place you will enjoy for the time you have. So a big city with lots to explore is one option. A smaller place is risky, if you know it’s somewhere you will enjoy just hanging out it could be a great relaxing time but if it’s not somewhere you love it could get boring and you are stuck there. If you have long afternoons free then somewhere with interesting places (beaches, small villages, hiking) within a 1 hour drive or train could provide a good change of scenery.

I would arrange my day so I have time free, either in the mornings to early afternoon or mid afternoon to evenings. So work 6-1 and have the rest free, or 1-8 or some other combination. A normal 9-4/5 will take up too much of the prime part of the day to enjoy your destination. Of course weekends still exist! Maybe you work longer other days and do 3 day weekends.

Also maybe use your actual vacation time right before or after your work visit and do a more typical vacation trip during that time.

There have been numerous times over the years when I took my computer/phone along and worked on vacation (including Europe); however, the total amount of time devoted to the work only averaged about an hour each day. I took the time to keep up with things and handle issues that would arise that needed addressing. Usually this was done each morning so I hardly even noticed I was working - so it definitely felt like I was on vacation. IF I could extend a 2 week European vacation by working 6-8 hours daily during the extension I would. It may not feel the same as vacation but you'll still have the non-working hours to enjoy. I've taken a lot of business trips when I worked all day and then enjoyed the remainder of my time like it was vacation. Make sense?

We have a home in a vacation destination where my husband will often work remotely. In the summer, this means he can go to the beach or play nine holes of golf after work or take a long break for either at midday. Also, his boss has to take children to school so rarely wants to start before 10. In a vacation destination, that can be time for fun as well. With your work schedule, you could plan your work around what you want to do for fun, i.e. work after the sights are closed. I think this is a great incentive for employers to offer and it won't cost them anything to do it.

Carrie, a question?
Would you need to be available to the office at home during work hours in their time zone? Say, would you need to be responding quickly to questions, participating zoom meetings, etc. which would require you to work in the middle of the night? For example, 4 am to 10 am in Italy is 9:00 PM - 3:00 AM. where I live in the U.S. Just curious as, if that's the case, trying to manage a sleep schedule on rotating work/no work days could be interesting. :O)

The time issues that Kathy and others mention could be an obstacle. However if you don’t have to be available during Central Time and can work your own schedule it can be relaxing to work in a different location. My husband has worked with his laptop at our house’s pool while sipping great coffee, eating freshly baked croissants and listening to cicadas and been happily productive. He’s also worked from a balcony listening to rushing water and looking at the Eiger, Monch and Jungfrau from time to time. A change of scenery alone can be worth it. The possibilities are endless!

My answer is similar to KBK's. In the past 25 years I have never not put in a few hours while on vacation; usually an hour or two before my wife wakes up and occasionally answering email the rest of the day. We typically will seek out a restaurant, bar or library with wifi so I can check in. For me it works, and saves me the stress of not being overloaded once I'm back. I get 5 weeks of vacation a year but have never taken more than 2 weeks in a row. I'd take your opportunity in a heartbeat.

I haven't done it (and never will, since I'm now retired), but I'd have jumped at the chance assuming I wasn't locked into always needing to be available for contact during the US workday. (In that case I'd have opted for Central or South America.)

What I have done twice is spend two weeks taking 3 or 4 hours of language lessons per day, which also involved some homework. So it wasn't a full day's work, but I had substantial time commitments that made the experience different from being on vacation. I found the situation had definite pluses. Aside from the obvious deep-dive into one location, it was relaxing not to feel I had to fill every possible moment with some sort of tourist activity. I could plan to go to one small museum a day and not feel lazy. I also nearly always managed to have one nice restaurant meal per day; when I'm in full-tourist mode, I too often prioritize sightseeing over food and settle for something casual and not so interesting.

I agree that selection of location is key. I'd want either a major city (one of the capitals, Barcelona or the like) or a major transportation hub with a wealth of quick side-trip options. In the latter category I commend Nice to your attention. That was the location of one of my language stays, and it was ideal: Six art museums in town, an historic district to explore, a nice market, cheap rail service to whisk me to any number of places along the Riviera, and bus service (slower) for visiting a bunch of inland towns. Lodging rates, at least in May 2017, were surprisingly reasonable.

My other language lessons were in Orvieto. I really enjoyed Orvieto, but for mixing classes and sightseeing it was a bit too small and awkwardly located for two weeks. It was hard to leave town on a day when I had lessons.

I will say that for me (not naturally an early riser), it worked best to have lessons in the morning so I was free later in the day. Without the imperative of getting up and being somewhere at 9 AM, I tended to fritter away most of the morning and do nothing except have lunch before an afternoon class. I don't know how much freedom you'll have in the scheduling of your work hours.

Planning this escape for the period when days are longest might somewhat reduce the impact of having to be available to your colleagues during their US working hours, if that's something you have to deal with.

Thanks for all the great, thoughtful responses so far!! They are appreciated and have given me a lot to think about.

As to my working hours, for the most part, my work is independent. I mostly summarize court cases and have the flexibility to set my hours. I might be encouraged to attend any meetings, but I’m not sure I’d be required to attend.

I am spoiled and already have a lot of vacation time. 7 weeks automatically + an option to buy 5 more + an option to carry over 5 days. So, I’ll most likely have 9 weeks to start with next year. But I do use some of my vacation days for doctors appoints and things like that.

My first trip to Europe will hopefully be later this year to Switzerland with my sister and her husband. Next year, the plan is Italy in the Spring with my sister and her husband and then a solo trip for me in the Fall. As of now, I’m thinking the solo trip will be back to Switzerland as I think I’ll feel less anxiety traveling alone there since I would be familiar with it and everything about Switzerland seems easy and safe to me. If I decide to go for extra time, I could do part in Switzerland and part elsewhere. I would also like to move around a bit and not stay in one location all the time. And of course there’s the added expense of staying longer, especially if that time is in Switzerland. And I do need to be on VPN to do my work, so good, reliable internet is a must.

Not happening for me! ;-)

I have worked and then immediately went on vacation, tagging it onto an existing trip, (or vice versa) which worked well. But there was always a distinction between the two with no overlap. I too had an extensive amount of time off in my last job which really helped with allowing the separation of the two. And never got the "I'm too important to actually take vacation" aspect of things, so never had that offered to me nor would I have ever accepted it.

I think that phrase "working while on vacation" is a misnomer. You're either working and 100% dialed in/ focused on work, or you're vacationing. If you're doing both simultaneously, you're probably shortchanging your work and your leisure time. Four weeks may not be a big deal, but several months of working from overseas will have tax consequences (you'll get caught having to file two sets of taxes - not worth it, I think - or at least something to consider carefully).
https://news.bloombergtax.com/daily-tax-report/an-eye-for-moving-abroad-bye-bye-usa-hello-tax-complications

The questions that need answering are: Can you do justice to your work while vacationing and Can you really enjoy your vacation break from work while working?

That said, I use to periodically check office/work e-mails when I had a break in vacation things with the concept of putting out small fires before they became big. But that said, trust your team to deal with the job while you are off the clock.

Technically, you aren’t allowed to work whilst in Europe on a tourist entry visa/visa waiver. Working 4 weeks out of a 6 week trip means the majority of the trip is work.

Personally, I would want to separate the holiday and work, otherwise work hours tend to creep into my time.

Jennifer, thank-you for pointing that out. It never occurred to me to check the legality of working while in Europe. I’ll have to look at the details of that restriction. I work for a legal publishing company, so I certainly can’t go around breaking the law. I remembering reading that some countries were welcoming remote workers. I’ll have to do a little research on that.

Agnes, thanks for the note about the tax implications.

And thanks again everyone. I always am so impressed with the wealth of knowledge you all have and greatly appreciate the willingness to share it with those of us who are less experienced.

I would jump at the chance! I have already asked my employer and got the negative on that, but in this new post-covid working environment I could see them being open to it in the future I just need to maintain my California residence which I obviously would, I am salaried and just get my work done with whatever that takes so I also have a lot of flexibility but live with a company issued cell phone on my person at all times. I would just need to transport or possibly rent two monitors and a docking station. The thought of being in Paris or Florence after a work day is better than my regular routine at home, plus on the weekends we could take day trips and explore. I would bring my husband and he is totally content doing his own thing, I am sure he can find a pool hall to occupy his time and he makes friends very easily. I would go in knowing I am working and I would add on vacation time before or after or in between. So work a week, off a week, work a week, off a week...

I will answer client emails while on vacation but my "out of office" assistant warns them that my replies won't necessarily be timely and that they should call my office and states the date I will be returning to the "office". But my office has been my home for 15 months now and will probably remain that way for the foreseeable future. I could easily work from anywhere in the world on or off vacation.

Here's my commentary on a recent relevant experience...in the States. I work from home but can essentially work remotely anywhere as long as I have a good computer, solid internet, and access to my digital files. Frankly, school schedules and kids' activities keep us tethered more than anything. Things have been super busy for me, so I had to work...a lot....during a planned family vacation. I actually worked MORE on vacation than I normally would during a standard work week, but c'est la vie. Heavy workload and lots of deadlines.

I worked late the last couple of nights before leaving to offset the travel day. We had a great place to stay with a swimming pool and other fun amenities and reasonable distance from the beach and several other fun sights and places. Most days away I woke up super early (with a time-change advantage) so I could get 8+ hours of work in and still be able to pull away for a half-day here and a couple hours there for a hike or bike ride, to go to the beach or visit a can't miss sight or event. Evenings were mostly free, so I was able to enjoy dinner and some evening events...and downtime...with the family.

Thankfully, I didn't ruin the vacation too much for the rest of the family, as they were able to enjoy some sights and adventures without me. We were originally going to travel back home on a Saturday, but we rescheduled to leave Monday so I could get a couple days of real vacation time over the weekend.

Not ideal as far as true vacations go, but a thousand times better than staying home. I count myself lucky to be able to work and travel...when necessary.

I wouldn’t worry about the legality of working your job for a few weeks in another country, and the same for worrying about tax implications, for a month stay or less.

I also think the whole telework from abroad thing is goofy unless you have a free place to stay. Else you are paying for holiday accommodations to live in while you are working when you are already paying for accommodations to house you while you work sitting empty at home.

Teleworking from the plane, that I can see.

Some would say that this is a question that only an American would ask. Unfortunately we have a son that because of his position and the type of work, can never be out of touch. His company issued him a secured phone and he must be available 24/7. Makes for unexpected and some times tough vacations. Only a few more years, he says.

Having done something similar, my preference would be to separate your work time and vacation time. Makes it easier to set expectations with work mates, and allows you to disconnect on days you designate as vacation. So it could be two weeks straight, a week at a time, or even long weekends for vacation.

For your work segments, you need to be in the work mood, and I would avoid moving around during your "work week". Park yourself in one spot, and stay until the weekend, or your next vacation segment, and have a set routine.

You are not really working during vacation, you are keeping the two separate, but yeah, instead of grabbing a bite at McDonalds at the end of the day, you get to go into a charming European town and have a great meal, maybe see a few sights.

As for the legality, visa and the such. What you are proposing is no issue. I am assuming that you are a US resident, working for a US company, and being paid in US funds through a US bank. In that case you are not doing anything illegal or violating terms of a tourist or short stay Visa Waiver, and you have no tax liability in the Country you will be visiting. The 90 Day Visa waiver actually allows for a great deal of types of work to be done without need for a Work Visa. The point at which it becomes an issue is: If you are a resident of that country or have a resident Visa; Are working directly for a Company in that Country; Being paid directly by a company in that country. Simply working remotely does not qualify as "work" in the sense that the Visa Waiver defines it. I worked for a Fortune 500 Company with International offices; we had a raft of people that managed the need for work visas, each trip required a questionnaire and description of what was being done. Basically, only a long term stay required some sort of Visa, and that was more for needing more time than the work. Every other time, we entered on the same Visa Waiver that everyone else did.

Honestly, my answer would be how available do they want you? Would you be expected to get up at midnight in Europe to work on an emergency at work? Would you be on call all the time? It sounds good on paper but employers can take advantage of this. I like my vacations to be vacations. My dad did something similar to you and he was working for half his vacation and TBH didn't enjoy it.

It depends upon how much flexibility you really have. Your situation sounds like it could work, but my experience was that work always intruded in ways that were not easily ignored. I was often involved in time sensitive situations that required immediate attention and from the US side (and also Asia) a tendency for my employer or customers to disregard that I was on vacation. I won't get into all of the intrusions I experienced but suffice it to say, they were constant as was my work. Having been down that road and since retired, I would not be interested. Being continually accessible is a lousy way to live, even if it pays really well.

In a heartbeat, I would have jumped at the opportunity to work overseas for 4 weeks. I’d take vacation time afterwards. For me, Spain would have been my choice since those remote work weeks would have allowed me to improve my Spanish in an immersion setting.