Remote Work Vacation: 5 Tips for Traveling

Part of what makes remote work beneficial for so many people is the opportunity to work from practically anywhere in the world. However, taking a remote work vacation might be challenging. Especially if you’re tempted to work the entire time you’re supposed to be enjoying time off.

If you have a remote job and you want to step away from your work-from-home routine to to travel or take an extended vacation, see our tips for taking a vacation as a remote worker. Additionally, we’ll cover a few steps to follow if you want to combine remote work with travel time.

1. Determine How Available You Plan to Be

If you plan to work even a little during your scheduled vacation time, you should set reasonable work hours expectations.

Including:

  • Yourself
  • Your clients and customers
  • Your place of employment

First, determine what your availability will be throughout the trip. Then, you can commit to booking decisions. From there, you can start your vacation with firm and clear boundaries.

Man sits on a laptop doing asynchronous work in a lawn chair beneath a mountain and trees on a remote work vacation
A remote work vacation is possible with the right planning.

For example, you might plan to remain completely off the grid during your remote work vacation. Or, you may spend 10-20% of your vacation time getting work done. Another option is to follow a 50/50 hybrid approach by taking a workcation.

You might even choose two different availability options.

These can look like:

  • Week one—unavailable for work/completely “off.”
  • Week two—50/50 hybrid approach, spending the mornings working remotely and spending the days “on vacation.”
  • Week three—working 10-20% of your time during the extended period of your travels.

2. Plan Your Schedule

When creating a plan, you need to consider the “unexpected” while you’re away. Examine your typical workweek and estimate how much work you can realistically expect to receive, then make a note of various due dates for projects you plan to complete.

Compare your predicted work schedule with your vacation schedule and look out for due dates that interfere with events or travel dates. This way, you won’t be scrambling at the last minute to submit work or meet deadlines before getting on a plane or leaving your hotel for a day out.

women gather around a table in a library discussing the benefits of flexible work spaces
One of the best remote work vacation tips? Plan, plan, plan!

Keep a well-organized list or spreadsheet that covers all of your important projects, dates, plans, and possible areas without an internet connection so that you can make adjustments as you continue preparing for an extended vacation. Here, you can see some of our favorite online management tools that may be helpful for remote work vacation planning.

3. Notify Your Colleagues & Clients

Once you know when your travel dates, notify your colleagues and clients a few weeks in advance. You’ll want to cover key pieces of information like:

  • The dates you’ll be gone and unavailable
  • Which projects you plan to complete while you’re gone
  • Arrangements you’ve made with colleagues who will cover some of your work
  • Your return to home office date
  • If you’re working in different time zones

Additionally, you’ll want to inform your clients or customers that you’ll be away and provide them with a predicted timeline of your planned absence. Let your clients know who they can contact if a sudden need arises while you’re on vacation.

If you plan to unplug completely for part of your vacation, don’t forget to set away messages and auto-replies from your work email account or any collaborative tools you use.

woman types on her laptop working on her freelance business with cup of steaming coffee in the background

4. Organize Your Workload & Make Arrangements

Depending on how much or how little work you plan to do during some or all of your vacation, you may need to make several work plans and arrangements with your clients and colleagues.

Let’s say you plan to travel from the beginning of June to the middle of August, and you’re going to be away from your computer from June 1st to June 14th. If you have any work projects due during that period that can’t be completed ahead of time, you might need to collaborate with your colleagues and have one or several of them take care of your workload during the first two weeks of your vacation, especially if you and your colleagues work asynchronously

If this is the case, be sure to provide them with all of the documents and resources they’re going to need to complete the tasks at hand in a timely manner.

View of Mirror Pond in Bend Oregon's Drake Park highlights reasons to take a workcation in Central Oregon
Organize your workload so you can take advantage of your vacation destinations.

Your availability might change partway through your vacation. For example, you might return to 50% availability from the middle of June to the end of your vacation in August. To satisfy the schedule you’ve set for yourself, it’s essential to plan your workload for each week you’ll be working while traveling.

5. Make It a Workcation

A workcation allows you to work remotely and travel simultaneously. Here, we’ll explore ways to stick to your work plans and enjoy your time off simultaneously.

If you’re following the 50/50 hybrid option, it’s important to have half of the workload you won’t be covering assigned to one of your colleagues so that none of your projects are submitted late.

As for the half you plan to do while you’re traveling, it’s a good idea to firmly schedule blocks of time that you need to dedicate to completing your tasks. It can be easy to get distracted or procrastinate when you’re trying to relax, so a stringent schedule that grants you the time you need without interruption is your best bet.

Keep a calendar of your entire work/vacation plan—and stick to it. Find or designate a working space so that you’re not wrestling with where to get situated with your laptop.

view of mountain in central oregon reflecting on the lake with pine trees lining the background
Take a workcation in Bend and get these views!

Avoid becoming sucked into performing more work than you signed up for during your absence. Maintaining a balance between your travel plans and your work responsibilities is essential in order to enjoy workcations. While you don’t want to put off work you agreed to do, you also don’t want to miss your entire vacation because you’re working a full schedule.

Coworking for Digital Nomads

With remote work, you have the best of both worlds. You’re free to travel, take time to recharge, and complete work from anywhere you happen to be. So long as you plan accordingly, have a backup plan in place, and set firm boundaries between vacation time and work time, you’ll be able to take care of your responsibilities and enjoy new locations as you please. Coworking spaces offer a greater work-life balance, allowing freelancers to find a working sanctuary should they need to plug in during a remote work vacation in a professional work environment.
Get day passes and punch cards for coworking, or join The Haven Coworking for as little as $149 per month.

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