woman working on beach with contracts

How to plan a remote work-cation to boost mental health

16 min read
Kayla Schilthuis-Ihrig

There’s so much inherent flexibility to the remote work lifestyle, but does that freedom ever feel like a distant memory? After working the same hours in the same space (and maybe even the same clothes) for too long, it’s natural to reminisce about the honeymoon phase of working online. So why not plan a remote work-cation to rekindle that initial excitement?

Working remotely is supposed to be all about freedom and joy. But if you’re left feeling unstimulated or lonely, this message is urgent:

It’s time to rethink your workspace and explore new environments.

No more daydreaming at the office. You have the ability to get out there and see the world, so why not jump at the opportunity? Choosing to leave remote work benefits (such as location freedom) on the table takes all the shine out of this lifestyle.

When done correctly, you can plan a remote work-cation that’s stimulating, creative and rewarding. Here’s how to make it happen.

What is a work-cation?

A remote work-cation is choosing to work remotely from a specific destination. It’s a hybrid work arrangement where you take your work with you to a desirable locale – somewhere you might only visit on a vacation.

A working vacation differs from a normal vacation in a few important ways:

Comparison Guide
A typical vacationA remote work-cation
  • Focus is on sightseeing
  • You choose your destination based on what there is to see and do
  • Duration is usually a week or two
  • The goal is relaxation or fun
  • Leave responsibilities at home
  • Situation escapism


  • Focus is on working nine-to-five, or close to that 
  • You choose your destination based on what it’s like to be there and how it feels different from home 
  • Duration can be two weeks (recommended minimum) to months 
  • The goal is improved mental stimulation 
  • Bring responsibilities with you Situation improvement


Planning a remote working vacation is not just a juicy daydream. This arrangement makes sense for workers and the communities that benefit from tourism capital. Some destinations are vying for these types of workers so badly that they’re obtaining grants and paying remote workers to come to their communities for a few weeks of productivity. (Take this initiative from the Pennsylvania Wilds for example)

Sometimes a whole family can apply for these remote work-cation grants.

Ultimately, choosing to plan a remote working vacation isn’t just for single twenty-somethings. Given the benefits, it makes sense to share the love for anyone needing an escape from the work-from-home routine.

What are the benefits?

When you plan a remote working vacation, you simultaneously take the initiative to improve your overall mood and avoid burnout. There’s a lot of research backing up the upgrade in:

  • Reduction of stress
  • Improved sleep
  • Mindfulness

But, we don’t really need studies to tell us what we already know, do we? Anyone that wants to plan a remote workingvacation already knows that they feel more relaxed and alive when they experience a new place.

The real payoff is tapping into what gives you a sense of fulfillment

According to Sahara Rose De Vore, Wellness Travel Coach and the Founder of The Travel Coach Network:

“Rather than being stuck in an office cubicle, working remotely can make working more exciting, interactive, and self-fulfilling. When we feel fulfilled and that we have a purpose, we feel better mentally.”

This really boils down to your “why” behind working remotely.You may have pursued a remote job for more freedom, travel and a flexible work environment. But are you taking advantage of these perks to prioritize your work-life balance?

Remote work is a lifestyle and it needs to work for you – or it ultimately will work against you.

So go ahead, plan a remote work-cation and create a positive event you can look forward to. You’ll feel an improved mental state every time you look at your calendar, rather than seeing endless deadlines and meetings.

Note: If you feel your mental health needs immediate attention, you should get help now. You can call the Substance Abuse and Mental Health Services Administration's (SAMHSA) national mental health and substance free hotline 24/7/365 at 1-800-662-4357. You can also immediately reach the Crisis Text Line via SMS or WhatsApp.

How to plan a remote work-cation in five steps

A remote work-cation has very different planning needs if it’s going to effectively prioritize your mental health (and not just create unnecessary stress). Follow these five steps to make it happen.

Step 1. Decide what you want to experience (once you’re done working)

Imagine that today when you’re done working and you close your laptop, you’re somewhere different. What is it you would want to experience?

Although it’s easy to get lost in the endless attractions or bucket list items a destination offers, you’ll want to consider the focus and perspective of your work vacation when planning.

Keep in mind, you won’t spend every day browsing a museum, going on a trek or having your third Coco Loco on a Caribbean beach before noon.

To help you narrow down a world of options, ask yourself the following questions to find the ideal environment for your working vacation:

  • Foreign or familiar?
  • Hot or cold climate?
  • Peaceful or bustling?
  • City or nature?
  • Beach or mountains?
  • Off the beaten path or bucket list highlight?

Notice we’re not discussing specific locations here. Even if destinations are popping into your head like bidders at an auction, don’t go down that rabbit hole yet. It’s more important to consider key environmental factors when planning vs. choosing a specific destination because it sets expectations.

Man standing underneath a pier at the beach
An evening walk on the beach provides an instant sense of being unplugged. Maryland, USA.

Step 2. Decide how long you want to go

My simple recommendation is to go for at least two weeks. But my honest answer is to go for a month.

Getting settled in takes time and you’ll want to block out two to three days on each end of your trip for for things like:

  • Finding the grocery store
  • Falling into a routine
  • Seeing all of the sights that interest you

Remember, it’s likely you’ll be working from nine to five most days. Make sure to leave ample time to soak in the full experience or your working vacation and the area you’re in.

Another tip is to anticipate travel mishaps. A missed ferry, delayed flight or issue checking into your accommodation shouldn’t wreck your workload.

Planning a longer stay could mean bigger discounts for Airbnbs

Oftentimes, booking an Airbnb for a month earns you more discounts – which is a nice incentive to stay longer.

Here’s how to see monthly prices for rentals in three easy steps:

  1. Go to Airbnb
  2. Select “I’m flexible” and “month” at the top
  3. Choose the months you’re interested in traveling
Screenshot on how to find a monthly discount on Airbnbs

The best monthly discount I’ve ever found was $2,000 off. This made a one-month rental price for an entire apartment I found in Lisbon, Portugal less than $600. You can see why I was eager to jump on this deal.

Looking for even more fun? See the different accommodations Airbnb rentals can get you around the world. If you have the flexibility and enthusiasm to stay beyond one month, the options and opportunities are plentiful.

Preparations you’ll need to consider when traveling abroad

For US passport holders, many countries offer 90 days of visa-free travel. Longer visits abroad are achievable by jumping from country to country or applying for a remote worker visa. Many countries are falling over themselves to initiate these kinds of visas.

If 90 days away from home isn’t enough, it’s probably a sign that instead of a remote work-cation, you should be researching how to become a digital nomad. Digital nomads generally have no apartment or house to return to and travel full-time while working online.

If your working vacation is something you don’t want to return home from, becoming a digital nomad may be the natural next step for you. But, before you get hyped up and start selling all your stuff on Craigslist, start with a month away.

Picture of writer working on laptop in between bus seats.
What happens when you don’t block off enough time for travel days? You end up cramming work into uncomfortable places, like me on this bus ride in France.

Step 3. Choose when to go

Summer is the most popular time to travel and I recommend avoiding this time frame, if possible.

Why? The peak season of any destination guarantees peak crowds and peak prices. Many destinations are equally as nice right outside of the high season window.

Even going at the lowest point of off-seasons is still totally fine in many locations. It all depends on what you want to experience at your home office away from home.

Picture of mountains in Peru.
In an entire day exploring popular ruins outside of Cusco, Peru in December, we saw only a handful of other people. Pisac, Peru.

Choose the right time of the season that fits your needs

Personally, I plan remote work to help me cope with winter. As a remote worker living in the Netherlands, my mojo doesn’t cope well when we go from 16 hours and 58 minutes of daylength in summer to 7 hours and 31 minutes in winter (but who’s counting?).

For example, I’ve already booked my winter remote working vacation in Alicante, Spain, where I’ll get nearly two hours extra daylight per day. Prioritizing the dates of your working vacation can be really helpful for remote workers with seasonal affective disorder (SAD).

Additionally, you can use a sunrise and sunset calculator to check the amount of daylight you’ll be gaining by temporarily relocating.

Screenshots of day length calculator.

Given the change in day length between Groningen and Alicante, I’ll experience one entire extra day of sunlight every four days.

Key considerations to look out for when choosing a season

Before you commit to a location based on season, think about the following factors first:

Research seasonal hazards (such as natural disasters) before booking. If you’re going in the off-season, identify what makes it less popular so you can tell whether or not it’s a breaking factor. For example, rain is fine but regular flooding is a concern.

Don’t trust Google Maps to see what amenities are open. This is especially true in the off-season. Even though you might see a list of normal hours online, things like grocery stores and restaurants may shut down for the off-season with no warnings. Ask your host or hotel specifically about the local amenities for the time of year you’re visiting.

Writer’s photo of a beach at sunset in Greece.
The moon rising over my walk to the grocery store in Galatas, Crete, Greece. It was a stunning walk every day but it was also unexpected. Google Maps said that there were several other open grocery stores closer to my rental, but they were all unexpectedly closed for the winter season.

Step 4. Choose your destination

We’ve arrived: the sexiest step of planning a work-cation vacation. As long as a locale has WiFi, there’s almost no wrong answer here.

In step one, you should’ve decided what you want to experience after your remote workday. The realizations you had during that step should’ve narrowed down your field of consideration.

An important reminder when browsing destinations is to pick something you will enjoy.

Deciding to go somewhere mega-popular just because it’s hyped up doesn’t mean anything if you aren’t specifically excited about what it has to offer.

Key tips when choosing your next destination

As you plan a remote work-cation, think about ways that’ll make your trip worthwhile. Here are a few tips to help you on your journey:

  • Look for contrast from your daily life. Going from New York City to Chicago is probably not going to provide a stimulating, creative escape.
  • Be extra cautious of time zone differences and jet lag. If you don’t have a flexible schedule, you may not enjoy waking up at 4 a.m. for meetings.
  • Seek out digital nomad guides to see if remote work needs are met. Some regions are host to big hurdles that normal travel guides might not mention. For example, South Africa’s power cuts shut off electricity for parts of the day to conserve electricity. This may be a big surprise if you’re not expecting it.

If you’re going the digital nomad route, check out these handy resources from select destinations:

Note: The digital nomad lifestyle isn’t exactly the same as a work-cation, but the destination-specific needs are very similar.

Step 5. Choose your accommodation

There are four golden rules to booking a remote work-cation accommodation that will make all the difference to your trip. Let’s review them below.

Rule #1: A real workstation

Working from the couch or a bed isn’t realistic for weeks of full-time work. In the absence of a workstation, look for nearby coworking office spaces.

Rule #2: Verify internet speed and identify a plan B

The WiFi always can (and usually will) be patchy or drop out from time to time. I’ve worked remotely from nearly 20 different countries and experienced this first-hand in various locations. It doesn’t matter if I’m working from a Caribbean island during hurricane season or operating out of the Netherlands on a sunny day.

If you book through Airbnb, you should ask your host to test their speed before booking. This is a new feature through Airbnb specifically for remote workers, so hosts shouldn’t be surprised by the request. Ask hotels, hostels, or housesitting hosts to test their speed as well.

A good remote work plan always includes a plan B.

So, look on Google Maps for anything nearby with WiFi that could serve as a short-term stand-in for emergencies during work hours. This could include:

  • Cafes
  • Coworking spaces
  • Public libraries
  • Fast-food chains and restaurants (McDonald's can really swoop in and save the day)

That last option may not be everyone’s top choice, but a cup of dirt-cheap coffee can buy you access to McDonald’s WiFi in more than 38,000 locations. It’s saved my bacon on more than one dicey occasion.

Pro tip: A good remote work time management habit to start practicing now is finishing everything at least one day early. If you combine a remote job and travel for long enough, eventually the WiFi connection will leave you hanging and you’ll be grateful to have thought ahead.

Rule #3: Look for a rental with a kitchen

Having to wander out for breakfast, lunch, and dinner eats away at your day and productivity. Being able to make food at your accommodation will save you a lot of time and money.

Rule #4: Seek out someplace quiet

Your remote work-cation accommodation doesn’t need to be pin-drop silent, but look out for a few red flags:

  • Street-level accommodation
  • Bars within earshot (check Google Maps)
  • Comments on the noise level in the reviews from past renters

A noisy accommodation may lead to poor sleep at night and lack of focus during the day.

For anyone who wants company on their working vacation or who finds planning too arduous, consider choosing a digital nomad co-living space instead of an Airbnb, hostel, or hotel.

Flexible remote workers can also consider housesitting to save money and get a very authentic (and free) experience with local life.

Photo of writer overlooking a balcony with Mediterranean city in background.
Watching the sunset over the Mediterranean every night from my Airbnb’s balcony made this an extremely memorable working vacation accommodation. Galatas, Crete, Greece.

How to balance working while on vacation

The right attitude is important when checking in for your remote work-cation. The following habits should serve you well:

Set goals for yourself

Consider how many hours you want to work, when you want to work and the various outcomes. Remember that you’ll likely feel extra creative, so try to minimize, batch or outsource ongoing tasks to your team. This will give you extra space for projects you’re excited about.

Finish everything ahead of time

Yes, I’ve already said this, but it’s vital to your experience. You should always anticipate hiccups. Today I’m house-sitting in the Netherlands and the WiFi has already disappeared twice and it’s not even 11 a.m. This is just a part of the gig.

Train yourself to be as focused as possible when you work

When a task or deadline takes twice as long to complete at home, you’re probably annoyed with yourself. When it happens on a work-cation, it’s demoralizing. Hone in on a set of tools and habits for staying focused online and you’ll enjoy much more of your destination.

Even though you may have to wait months to take your actual remote working vacation, these are all habits you can work on right now. How exciting is that?

Photo of writer overlooking a canal in the Mediterranean.
Exploring Venice for a few days before settling into a month-long working vacation on the Mediterranean.

Next steps

So, will I be bumping into you in Alicante this winter?

No matter where you decide to go, the tips above will help you plan a remote work-cation that improves your mental health – instead of just testing it.

Remember to answer these questions before you book:

  • What do I want to experience at the end of my workday?
  • How long can I afford to be away for, both time-wise and financially?
  • When do I want to go on my remote work-cation?
  • What type of accommodation will I look for?

If planning all of this yourself is leading to analysis paralysis, consider participating in a remote work program where someone with experience planning work-cations handles the big decisions.

As long as it provides mental stimulation and reduced stress, a successful working vacation can take almost any form. You never know what good is waiting to strike once you put yourself in a creative and inspiring space.