Tips for Planning a Workcation to Have the Best Time

Published by Jeremy. Last Updated on December 7, 2023.

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If you are able to work remotely, odds are good you've thought about taking a workcation.

Workcations are often the best of all worlds. You get to work in a cool destination, enjoy the area in your free time, and do it all with little (if any!) paid time off.

But planning a workcation isn't quite like planning a regular trip. There are a number of special considerations you will want to keep in mind for your work. So in this one, we thought we'd share some of our best tips to get the best out of your workcation!

Travel Logistics During a Workcation

Working on the Beach

Travel logistics are one of the first things you must consider when planning a workcation. How will you get to your destination, will it fall on a workday or not, and does the method of transportation require you to go offline for an appreciable period of time?

This is simply one of the easiest considerations because you may not have many options to reach your destination. You may have to take PTO if your travels fall during a workday. If you can swing it to travel outside of business hours, you may be able to get to your destination without taking extra time off but may risk eating into your available free time (e.g. traveling on Saturday may help you avoid taking an extra day of PTO, but if you take some time off to travel on Friday, you get that Saturday to have fun.)

The availability of travel options from A to B is often the limiting factor here, so there is not much we can say beyond pointing out that this is the first topic to consider when planning a workcation. In many cases, you'll need to make a conscious decision on what is best for your trip.

Time Zones for Work Hours

One of the best and worst problems of planning a workcation is dealing with time zones if you have to maintain set working hours (say, Eastern Time).

Things get tricky here for many reasons.

Let's say you stick to your same time zone on the trip and work a conventional 8-5. Does your destination have ample early morning or late night activities for you to fill your free time with? It would be a shame if nothing is open in the morning for breakfast and all attractions are closed before you are off at night, after all.

What if you head west and go back two or three hours? Can you get up at 5 or 6 am to work the same hours (if you are required to work at set times)? If yes, you have the tangential benefit of being done with work by 2 or 3 pm, opening up more time in the day to explore. If not, you have yet another issue to contend with.

What about traveling east, say, to Europe? Five to six hours ahead would put your work schedule from 8 am to 5 pm to about 1 pm to 9 pm (or later). This certainly frees up mornings to do activities, which can be great in most destinations but leaves little time in the evening to eat or explore. Some destinations (e.g. southern Europe- Spain, Portugal, and Italy) have much more vibrant late-night cultures in cities than others (like most northern Europe destinations). 

Beyond these, further travel outside your home time zone exacerbates the problem even more. Will you work overnight? Get up at 2 am? The timing logistics here are near endless and simply are a function of how flexible your job is and what the destination can accommodate.

Accommodations For Convenience

Another consideration of a workcation is the kind of accommodation you are booking.

A conventional hotel could be good for modern amenities. But if you need to cook meals while working (as we often do to save cost), you may want to consider ensuite-style rooms with kitchenettes to have some essential cooking equipment. That could inherently limit the number of options.

Apartment rentals tend to boast broader amenities that would work well with workcationing, but you're inherently at risk for other issues. For example, what would you do if the WiFi doesn't work as advertised? Do you have a hotspot and a data plan to cover any outages? Hotels run this risk too, of course, but may have more areas where internet connections are plentiful, such as WiFi in a common area or wired connections in a business center.

Of course, there are also the added considerations of check-in and checkout times and how they may influence your work day. A meeting at noon may be fine until you find out that hotel checkout is also at noon, and you have to leave the privacy of a hotel room outright. Having a few backup spots ready to go for internet (e.g. a nearby cafe or brewery) can be a good safety net in a pinch.

Time for Fun on a Workcation

In a previous section, we discussed planning a location based on having time for fun at off-hours, but we can take this one step further.

A perk of taking a workcation is to extend a trip to somewhere fun on fewer PTO days. Go somewhere for two weeks but want to work weekdays? You still get upwards of five or six weekend days for free depending on when you travel. Throw on a day of PTO? Well, now you may have a three-day weekend to explore somewhere fun.

The trick here is that not all destinations are enjoyable on a partial schedule. A base in one city for an extended period is often a great idea, and a long weekend can be a nice way to round things out, either in the city or somewhere close by. But you may not get a full vacation experience out of it compared to taking a full two weeks of PTO for a custom itinerary that hits several destinations in one go.

As such, you may need to be strategic on planning where you go at all simply to feel like you're doing a destination justice despite working. If the travel requirements, number of days of PTO, or other factors add up, it may end up being a detriment to your trip from the start!

Overall, while planning a workcation is not much different than a regular vacation, all of the above considerations play off of each other. One destination that may sound fun for the time zone may end up being poor due to off-hour amenities or for WiFi backup. Another destination may be perfect for off-hour experiences, but you may want to see other destinations nearby that you don't have time to hit while being semi-isolated for work.

This, naturally, will be heavily dependent on your own situation, but be sure to keep these tips in mind when planning your trip!

What is your favorite tip for planning a workcation? Comment below to share!

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About Jeremy

Jeremy from Living the Dream

About the Author: Jeremy is a full-time travel writer based in Pittsburgh and primary author of this site. He has been to 70+ countries on five continents and seeks out new food, adventure activities, and off-the-beaten-path experiences wherever he travels.

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