Are Working Vacations a Good Idea? Pros and Cons Working From the Road

Equipped with a laptop and wifi, more people than ever are embracing the remote work life. And not just from the comfort of home, but the working vacation life. It seems like a win-win. You travel, you pay the bills. But what are working vacations really like? We’re breaking it down so you know exactly what to expect.

What is a workcation?

A working vacation, or workcation, involves traveling and working during the same trip. The term “vacation” is a little counterintuitive because when you’re taking a working vacation, you can’t unplug completely. You’re splitting your time between work and vacationing. That’s why we like to refer to the two activities as “travel” and “work”. But in essence you are working part of the day and enjoying new surroundings for the rest of the day. And it’s quickly becoming the trendy way to work.

What is a typical day like during a working vacation?

During a working vacation, you may work standard business hours. So you’ll wake up and enjoy the morning wherever you happen to be. And then you log in to work from your condo, RV, airbnb, or wherever. After a full day of work, you have the evening (and weekends) to explore.

Or if you don’t work standard business hours, maybe you split your time differently. You could wake up early to crank out some work and then take the afternoon off. Or vice versa. Normally, you’re working your regular schedule, just in a different location.

What are the benefits of a working vacation?

Working vacations have become a popular way to travel for several reasons:

Working while traveling means you generally can take longer trips since you don’t have to take time off
You can hop from place to place and experience several destinations in one trip
You get a break from your home office
It increases creativity
It can sometimes be a more affordable way to travel
You can experience destinations you never thought would be possible

Will it make you more productive?

A working vacation can absolutely make you more productive. If you’re in an office or have other distractions at home, getting away for awhile can help with your efficiency. And probably the biggest reason – your happiness level goes up. You’re vacationing, so naturally that will lead to a little mood boost. And people tend to be more productive when happiness is higher.

The caveat here is when your working vacation actually causes you more distraction. For instance, if you are bringing kids and those kids would normally go to school or daycare. Now you are having to balance work, vacation, and childcare. That increase in responsibility could lead to lower productivity. There are ways to work around it, but be aware how productive you can actually be.

Some tips to increase your success

Remember the time change

If you have regular meetings, you always want to think about how time differences will impact your work. For example, if you live in New York and you want to workcation in Hawaii, that’s a 6 hour time difference. If you have regular 9 AM meetings, you’ll now be taking those meetings at 3 AM.

Not everyone has strict meeting times, but if you do, factor it into the planning process and think about places with closer time zones.

Set a schedule for yourself

If you don’t set boundaries – it’ll be hard to maintain a work/vacation lifestyle. Vacation and work will blend together, and you’ll end up working while you’re out and about exploring. Which defeats the purpose of a successful working vacation. Or you may end up less productive because you don’t have a defined work day.

Bypass this hurdle by setting work hours and stick to them. Outside these hours, vacation and do your thing. But within your defined work hours, focus only on work.

woman working on computer from mountains

Make sure you have reliable wifi or phone reception

When you’re working from the road, plan ahead so you won’t be in a sticky spot. When we were RVing out west, there were so many areas with non-existent wifi. We functioned by using our phone as a hotspot, but even cell reception wasn’t always available in states like Wyoming and Montana. A lot of state parks are this way (even in more populated states like Florida).

Related: How to Plan an Epic Cross Country RV Trip on a Budget

It’s not just for RV work vacations either. Wherever you plan to be, double check the wifi situation. It’s pretty standard with most condo and airbnb rentals, but it’ll add an extra roadblock if you find yourself without it.

Find a comfortable spot to work

On a working vacation, it can be super tempting to plop down wherever and crank out some work. The beach, a park, a cafe. And these aren’t bad ideas per se, it can just make work harder if you don’t have a dedicated space. I recommend choosing a spot as your “office” free from distractions. The problem with working in public spaces is that it often comes with distractions, which can make you less productive.

Setting up camp on a balcony overlooking the ocean is a perfectly good office location. Just make sure it’s comfortable and free of interruptions.

Are some destinations better suited to work vacations than others?

While you can work and travel pretty much anywhere, there are some places better suited to the lifestyle. Let’s break down some of the more common vacation types:

RV/Cross Country Road Trip: Speaking from experience this one can be tough, but still manageable. Many RV parks claim to have wifi, but in practice it’s not all that reliable. You can get by, it’s just harder and takes more planning. Camping at state parks or national parks can be an added challenge as most don’t have wifi and some don’t even have cell reception. One benefit to this kind of trip – it’s one of the more affordable ways to travel for an extended period of time.

Beach Vacation: This is one of the more popular work vacation types. Split your time between working and hitting the beach. It’s popular for a reason – you can truly recharge when you have the beach steps away (even when you’re working part of the time). Plus, most of these destinations are in populated areas, making it easier to stay connected.
International Travel: For a lot of people, spending time overseas can be a bucket list way to travel. Many of these countries have so much to see and do. And spending weeks there can really do the place justice. If you’ve ever wanted to experience what local life is like in Italy. Or Japan. Or Bali. Wherever you’ve always wanted to go, planning a working vacation can allow you to do it without being constrained by vacation time.

How much time do you need for a working vacation?

Trip length will largely be determined by your job and budget. If you have the budget and your job will allow you the flexibility, you could take a long workcation. This type of travel typically lasts a couple months to a year or more.

The other option is a short term working vacation. And this could be as short as a few days or as long as a month or two. There are pros and cons to both, but I recommend starting off small to see how productive you find your trips. And you can slowly increase the length of your trip if you find it a workable arrangement for you.

What is a work remote visa and which countries offer them?

A remote work visa allows visitors the opportunity to live and work in certain destinations long term. In return, the hope for these countries is that visitors spend money to support the local economies. What are some of these locations?

Bermuda (up to a year)
Iceland (up to 6 months)
Montserrat (up to a year)
Mauritius (up to a year)
Antigua and Barbuda (up to 2 years)
Aruba (90 days)
Portugal (up to a year)
Barbados (up to a year)
Cayman Islands (up to 2 years)
Dubai (up to a year)
Mexico (up to 4 years)
Spain (up to a year)

Requirements vary for each country, but many require proof of income and health insurance as part of the application process. Many have restrictions for whether you can be company employed or self employed. And then there will likely be some type of visa fee ($500 for an individual or $750 for a family as an example). Fees range from free to up to $3000 for a family application in some locations.

What are the disadvantages of a working vacation?

While working vacations offer many benefits, there are a few drawbacks to consider before setting off into the sun.

It’s not a complete break from work. And some people blur the lines between vacation and work, which can lead to a less relaxing experience.
It can be expensive. If you have a mortgage or rent to pay, and then expenses for a vacation on top of that, the costs can quickly add up.
You may need a visa. The process will be easier if you travel domestically or to one of the locations above. Otherwise, each country will have specific requirements, and it may be difficult to obtain a work visa.

Can you really work and vacation at the same time?

You can be successful taking a working vacation if you set the proper boundaries. Where most people go wrong is they try to overlap the two. If you’re sending emails while sitting on the beach, you’re not truly vacationing.

toddler pretending to work on phone and computer

When we workcation, we define our work times. And during those times, we work. We don’t play or go out and try to work at the same time. Outside of those times however, activities are up for grabs. We try new restaurants, experience the local culture, and do all we can to unwind.

So yes, working vacations are really that – splitting your time between work and vacation. But it requires self discipline. And this is what separates success stories from failed working vacation attempts.

And don’t forget to treat yourself to an actual vacation too. Working vacations are great, but because you can’t unplug completely, they aren’t a perfect substitute for typical vacations.