take a working vacation

How to take a working vacation

If you’re lucky enough to be able to work remotely, your ability to travel becomes almost limitless. While working on vacation may not be for everyone, it can be a good way to have a much needed getaway without digging into precious vacation time. Here are some things to consider when planning a working vacation.

Plan to stay a while

With your ability to actually do anything at your destination greatly reduced by your work schedule, you’re better off staying long enough to make use of at least one weekend, preferably two. That way, you can enjoy your evenings and weekends off while you spend the rest of your time plugging away at work like you would normally do at home. If you consider value, going for just 3-4 days and working 80% of that time may not be worth the trip at all. But if you can get at least two weekends out of it, a working vacation may be just the right amount of vacation you need.

Pick a destination that’s affordable

If you’re going to stay a week or more, you want to make sure you’re not paying an arm and leg to be there. Choose a place where you can comfortably afford to stay in a hotel or vacation house for cheap. This way, your half vacation doesn’t cost you as much as you would want to pay for a traditional work-free trip. Choosing an affordable destination can also save you when you’re getting take out lunches or room service every day.

Pick a destination where there isn’t a lot to do

This kind of vacation doesn’t really work in a major city with lots of sights. Chances are, you’ll be working during hours when most sights and museums are open and you’ll miss out on a lot. And being cooped up working in a cramped hotel room in Rome or Paris is probably more depressing than it is refreshing. A good working vacation destination is one where you don’t have a ton of things to do except lounge around. Think beaches, remote mountains, quiet lake towns, and desert resorts. The point is to be able to relax and do nothing while still getting paid. That midday Zoom meeting is gonna be a lot less of a drag when you can attend it from the hotel pool.

Consider time zones

Whether your boss knows about your working getaway or not (although what your home office looks like is none of their business either way), you will still want to think about time zones when you plan your trip. Being in the same time zone might be advantageous so you don’t lose sleep, but it’ll eat up most of the daylight hours on your vacation. Sometimes changing time zones works in your favor. For instance, working Eastern Standard Time business hours in Central Europe means you’ll have your entire morning and part of your afternoon to do as you please, but you’ll be eating dinner in your hotel room while you work late into the evening.

Change your weather

Even if you’re not going to get up to much, a trip instantly feels like a vacation if you can escape a freezing winter and go somewhere with warmer weather or vice versa. Sometimes we get bogged down by more of the same at home, so getting to bust out the clothes that are put away for the season is enough cause for a getaway.

Make the best of local dining

working holiday

If you’re in the hotel room working half the time, you can save a lot by grocery shopping and cooking some simple meals like you would at home. If you choose ingredients you don’t normally have access to, you can still enjoy a little bit of the local flavor without spending a ton of money. Then you can dine out after you’re done working. You’ll save even more traveling this way if your hotel has free breakfast.

Alternatively, if you have the budget for it or you’re in a remote location without easy access to restaurants, you might opt for an all-inclusive package so you can have on-demand meals (and booze) all day long. So even if you’re working the entire trip, you’ve eliminated the daily hassle of feeding yourself.

Make sure the WiFi is good

If you plan to be connected to the office on your vacation, you need to make sure you can be connected. One of the things to look for when you’re searching for recommendations is good WiFi. Though free WiFi usually comes standard, the strength and stability can vary. Reviews will usually mention issues with WiFi, so keep an eye out for any warnings that might make your working vacation more stressful than you want it to be.

You may also want to do some digging to see if WiFi is available throughout the property or just in the rooms. What use is a sprawling outdoor pool and lounge area in the hotel if you can’t spend your day working there? When in doubt, ask in advance.

Spring for the sea view room

There’s a delicate balance between saving money and having enough of a good time for the trip to be worthwhile. So you’ll want to seriously consider your room or vacation rental amenities. After all, your accommodation is where you’re going to spend most of your time. So spring for the room with the view, get the private balcony, the cozy living room, or private whirlpool. If your room is nice enough, you won’t even feel the need to leave very much. Which is kind of the whole point — relaxed fabulous vacation vibes with the ability to get some work done.

And that’s how you successfully plan a working getaway without touching your PTO. If you think about it, if you make as much working during your trip as you spend there, your vacation is technically free.

working vacation


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