10 Tips to Help You Plan a Successful Workation

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The last year has brought about a remote work revolution. It's a shift that's long been predicted (I talked about it years ago when I first wrote about tips for working from home), but it accelerated at warp speed when the pandemic hit.

The move towards a largely remote workforce happened nearly overnight, and it's likely that many people forced into remote work by the ‘Rona will continue to work remotely indefinitely – if not permanently!

The increase in remote work combined with people getting worn down by pandemic restrictions has led to a rise in a totally new kind of travel: the workation.

Combining work and travel certainly isn't a new thing; in fact, the term workation isn't even new – it's been around for at least a few years! But never before have so *many* people been craving a change of work scenery all at the same time.

Countries from Iceland to Aruba are now even offering special long-term visas to entice remote workers to stick around for a while.

Amanda with flamingos in Aruba
You can make new remote working friends in Aruba.

But if you're new-ish to remote work, you might be wondering how to plan a workation that actually… well, works.

After all, planning a trip for fun is very different from planning a trip where you need to get a certain amount of business done.

The good news is that I can help you out! I've taken a couple work-centric trips in the last few months, including a dedicated workation with a friend to a cabin in the Great Smoky Mountains (AKA the Smokies) in February. I'm distilling everything I know about combining work and travel into 10 essential tips to help you plan a successful workation.

Why take a workation?

First of all, why would you even want to plan a workation in the first place? Isn't it just better to take time completely off work and travel instead?

Well, in more “normal” times, it might indeed make more sense to take time off work instead of trying to combine work and travel. But with many borders still closed and lots of people getting itchy feet, now is a great time to escape to somewhere secluded to both work AND relax.

Amanda in a rocking chair looking out at snow
A winter escape to the mountains

Going on a workation can help preserve your paid vacation time while also satisfying that travel itch. You can also go somewhere for longer, enjoying a bit of slow travel without having to leave your job.

And you'd be surprised how much a simple change of scenery can positively impact everything from creativity to productivity.

Before my recent workation, I was definitely in a creative rut. I wasn't motivated to do much of anything, and this blog was definitely suffering for it. After a 10-day workation in a relaxing, secluded spot in the mountains, though, I almost felt like my “old self” again and returned home ready to get back to work.

Sunset over the Smoky Mountains
It would be hard not to be inspired after sunsets like this!

10 things to consider when planning a workation

If you're thinking that this whole workation thing sounds like something you might like to try, you're probably curious about how to go about planning one. After all, there's more to it than simply booking a hotel room near a beach!

So to help you out, here are 10 important things to consider as you plan your own workation:

1. Can you take a workation?

The first thing you need to figure out is whether you can even take an extended workation to begin with. If you're already working remotely from home, chances are the technical answer is yes.

For someone like me who is her own boss, the answer is always yes; I have no set work hours, and can work from anywhere with decent wifi. My friend who I traveled with to the Smokies can similarly work fairly flexible hours.

Working in a mountain cabin
We can both work from couches in cozy mountain cabins.

If I were to plan a workation with my husband Elliot, however, he would probably need to clear it with his corporate boss and make sure he could be available during certain core working hours – though that really isn't a major concern unless you're traveling into a different time zone.

You also want to think about easily you can adapt to a new work environment. Working from a new locale is definitely not the same as working from your home. In some cases, a workation might not be the best fit for everyone – and that's totally fine!

If you decide it IS the sort of trip for you, though, then you'll also want to ask yourself these other questions:

2. Which part will you focus on more? The work or the vacation?

Blue-hued Great Smoky Mountains
The blue-hued Great Smoky Mountains

Before planning a workation, you need to sit down and decide what you ultimately want to get out of it. Do you want to simply do your normal job from a new locale, or do you want to work a bit less and focus on the vacation part more?

Deciding how much emphasis you want to put on each half of the workation equation can help you make all the other decisions you need to make, from where to go to what kind of accommodation to book.

Some people may decide to work regular hours and use evenings and weekends to explore their new surroundings, while others may opt to work half-days or take days off completely in order to explore more.

For example, I took a brief solo workation back in January to stay in a tiny home near a state park in Ohio. And while I did go with goals of getting some work done, I also wanted to visit Hocking Hills State Park to do some hiking. I split my time half and half between working and exploring.

Waterfall in the Hocking Hills in winter
A scene from one of my Hocking Hills hikes

For my workation in the Great Smoky Mountains, however, my friend and I knew we were mostly going to focus on the work part. We weren't planning to cancel any scheduled meetings or go on any specific outings, and were more concerned with what our rental cabin had on the inside than what was around it outside.

Want to check out the cabin we rented in the Smokies? You can find it here on Airbnb.

3. How far do you want to travel?

Once you decide the overall goals of your workation, you'll need to decide how far you want to travel.

In our current pandemic times, it might make more sense to focus on destinations within driving distance instead of places you need to fly to, but that will obviously change in time.

Newfound Gap in the Smokies
Destinations within driving distance are my focus right now.

For my 2021 workation trips, I've opted for destinations within one day of driving that have lots of things to do outdoors and plenty of unique rental options. Choosing a place I can drive to also means spending less money on getting there, and being able to pack more comforts from home.

For example, my friend and I packed a car full of groceries for our trip to Tennessee, and brought homey comforts like our own pillows and stash of candles.

I have a feeling secluded, outdoorsy workation options are going to continue to be popular throughout this year.

Snowy cabin in the woods
Cabin stays are in very high demand right now!

4. How long are you planning to stay?

The toughest thing to decide might actually be how long your workation will last.

People who work and travel full-time will often settle down in one location to work for anywhere from 1 month to 1 year. But if you have a home base with kids or pets or plants to worry about, then planning an extended workation might not be feasible.

I'd say that a productive workation should be at least 1-2 weeks long, but probably not much shorter. That way you have time to settle into a new routine in a new environment, but won't feel like you have to rush to do any of the vacation-related things nearby.

My trip to the Smokies was 10 days long, which was a good length during winter in pandemic times. Though I'll admit that I could have happily stayed in the cabin we rented for a lot longer!

Cabin living room with fireplace
This was not a difficult place to want to stay longer.

5. How close do you want to be to the “vacation” parts?

Even if your workation is going to focus more on the “work” part of your life, chances are you'll still want to get out and explore your new surroundings. You therefore need to think about how close you want to be to the action, which can include everything from museums to hiking trails to restaurants to grocery stores.

When we were planning our Smokies workation, we knew we wanted to avoid the crowded areas of Gatlinburg and Pigeon Forge and stay somewhere a little more secluded. But we wanted to still be within driving distance of a grocery store, and did want to visit Great Smoky Mountains National Park at least once.

We eventually decided on a cabin on the Tennessee side of the Smokies, but chose one that was about half an hour outside of Gatlinburg. We were close enough to the essentials, but far enough away to not be stressing about noise or mask-less tourists.

Sunset at a cabin in the Smokies
The cabin community we stayed in was super quiet.

6. Do you want a rental or just a hotel room?

Once you decide where you want to go and for how long, it's time to start searching for the perfect place to stay. What's “perfect” for your workation will likely depend on several factors, including how long you're staying, how much work you're planning to do, what your budget is, and more.

For a shorter workation where you're planning to split your time between working and traveling, a nice central hotel might be just fine. But if you're staying for longer or are focusing more on work, then a rental with more privacy and amenities might be a better fit.

In our current reality, self-contained Airbnb rentals have been super popular. This makes sense, and are probably what I would lean towards when looking for a place to stay longer term. (Some Airbnb hosts will even offer discounts when you stay for a week, a month, etc.)

Airbnb search
You can now even search for week-long or month-long rentals on Airbnb.

7. What sort of space do you need?

The obvious things like number of beds and bathrooms are of course important to pay attention to when you're looking for a place to stay. But there may be other things you need, too, like a kitchen or a workspace.

When my husband Elliot and I took a road trip around Michigan last fall, we were only doing take-out meals. And I can't stress enough what a difference it made to have a place to eat meals that didn't involve sitting on a hotel bed!

The same goes for having a dedicated workspace if you're going to be working from a new space for a while. I have indeed worked from many a hotel bed on my travels, but it's NEVER my first choice if there's another option.

When my friend and I were planning our Smoky Mountains workation, we knew we planned to cook all our own meals – meaning a full kitchen and dining area were must-haves in any rental listings we looked at.

Smokies cabin interior
Kitchen and dining area? Check and check!

8. What is connectivity like?

If you work remotely and the main goal of your trip is to get work done, then it's very likely that wifi connectivity is going to be super important.

A place might look great on paper, but if the wifi is bad and there's not great cell signal, then you're going to have a frustrating time trying to get any work done.

This secluded treehouse is beautiful, but with no wifi or cell signal, it doesn't make a great workation destination.

So how do you gauge how good the wifi *actually* is? If you're booking a hotel, I would recommend heading over to a site like Booking.com to read property reviews; people will almost always mention if the wifi was terrible in their reviews.

If you're booking an Airbnb, your best bet is to reach out to the host beforehand; any good host will answer messages from prospective renters, and most should be able to give you an honest assessment of how strong/fast their wifi is.

If you're traveling abroad for your workation, you may also want to invest in your own wifi hotspot. I frequently travel with my Skyroam Solis, which lets me work from the road without the stress of relying on local wifi.

Our Skyroam wifi hotspot in New Zealand

9. Are there other amenities you need/want?

When it comes to renting a cabin or beach bungalow or any other space for your workation, I know it can be daunting – there are so many options out there!

I recommend making a wishlist of features to help you narrow it down. These can be practical features like access to laundry or maybe extra space in which to work out if that's part of your normal routine, or they can be luxurious touches like a great view or access to a pool or hot tub.

When planning our mountain cabin workation, my friend and I had extras on our wishlist like a cozy living area with a fireplace (since we were going in the winter), nice mountain views, and of course a private hot tub!

Hot tub sunsets in the Smokies
The hot tub was a must for us!
Snow on the Great Smoky Mountains
And the mountain views weren't bad, either!

Basically, you want to rent a space that will work well for YOU and your work/life style. If you really need to follow a certain routine in order to be productive, make sure whatever space you book is conducive to replicating that routine.

10. Do you and your travel partner(s) have similar work routines/styles?

Taking a solo workation is of course always an option, but chances are if you're planning a work-and-travel combo, you might be planning to travel with a friend, significant other, or maybe even your whole family.

In this case, it's really important to chat beforehand about your work style and routine, and make sure that nobody will have to sacrifice too much.

For example, the friend I planned my workation with has a very similar remote work style to mine: we both like to start our days with coffee and breakfast, and both enjoy background noise while we're working (we watched a lot of Schitt's Creek on our trip!). We both even agreed on candle scents to burn as we worked!

We also both had the flexibility to decide on a warm, sunny weekday that we would take the morning off to go on a hike in the national park and catch up on work later in the day.

Great Smoky Mountain National Park view
Getting to know Great Smoky Mountain National Park
Off on a hike
Laurel Falls

If you're traveling with someone with a very different work style/routine to yours, then you'll probably want to look for a property with separate work spaces, and talk about any potential issues before you leave home.

RELATED: What Working Remotely is Really Like + 7 Tips for Working From Home

Are there any downsides to a workation?

You may have already identified a few of the downsides you might encounter when you plan a workation. Personally, I think the positives outweigh the negatives, but you may not agree!

A few of the downsides can include:

  1. It can get expensive – Whether you're staying in a hotel, a tiny home, or a cabin in the woods, obviously staying somewhere for weeks at a time can get pricey. For example, the cabin my friend and I rented costs about $210 per night, which certainly adds up when you're staying for a while.
  2. It's not a vacation – This one is obvious, but unless you work entirely for yourself, you'll still be expected to be productive on a workation. If you're traveling with other people, you'll want to make sure you're all on the same page about how much time will be dedicated to work and how much to vacationing before you book your trip.
  3. It may not work for you – I'm used to working from all sorts of different places, so settling in to a new space for a workation happens pretty quickly for me. But if you are really attached to your routine and at-home workspace, it might not be so easy to be productive somewhere else. If you're worried this might be the case, you might want to try taking a shorter workation (maybe 3-4 days) to test it out before committing to something longer term.

Good workation properties

I obviously can't speak to anything abroad since I haven't left the country in about a year and a half at this point, but here are a few places closer to home I've stayed in the last year and can personally recommend for a workation:

Lake Erie beach houseThis house in North East, Pennsylvania has its own private beach, 4 bedrooms, and is close to several wineries. I rented it last summer through Vrbo, though it was mostly for a vacation instead of work. (Read more here.)

Lake Erie beach house
This beach house was awesome.

Hocking Hills tiny homeThis design delight is perfect for a shorter workation in Ohio. It has everything you need (including hot water and wifi), and is close to Lake Logan and Hocking Hills State Park. It's rentable on Airbnb.

Hocking Hills Tiny Houses the Juniper
This tiny home was perfect for a short workation.

Smoky Mountains cabinThis is the cabin my friend and I stayed in last month, which was absolutely perfect for our girls getaway workation. It has 2 bedrooms and 3 full baths, a rec room, two fireplaces, and hot tub, and mountain views from three different balconies. Also available on Airbnb.

Smoky Mountains cabin
Loved this Smokies cabin, and would definitely book again!

You can also check out some of my Airbnb guides for other workation ideas:

Personally, I feel like the workation trend is here to stay. As more people move to working remotely on a permanent basis, I think trips like this are only going to become more popular.

I know I'll probably plan at least one more workation this year, if not more!

Hopefully these tips can help you plan a successful workation of your own.

READ NEXT: How to Plan a Trip During a Pandemic

Have you ever taken a workation? If not, would you like to plan one?

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"It's a dangerous business, going out your door. You step onto the road, and, if you don't keep your feet, there's no telling where you might get swept off to." - JRR Tolkien

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