Workcation guide: 7 steps for working remotely in your second home

Published Date: November 13, 2023

A woman in a yellow shirt sits in a kitchen with her laptop on the counter, likely enjoying a workcation.
There’s no getting around it: Remote work is here to stay. In fact, an estimated one in four Americans are remote workers.The flexibility of working wherever and whenever you want means it’s finally practical for families to take extended workcations away from their primary residence — whether that be on an extended cruise, road trip or even a vacation home. By learning to balance work and play within your home — or second home — you can have a more fulfilling career as well as a more rewarding lifestyle. Follow this step-by-step workcation guide to do just that.

What is a workcation?

A Venn diagram compares traditional work, workcations, and vacations.
What is a "workcation?" Unlike a typical vacation where you disconnect entirely from work, a workcation allows you to maintain a work schedule and commitments. However, the setting is shifted to a more desirable or relaxing location, be it a sun-soaked beach house or a serene ski resort. A workcation lets you enjoy a change of scenery without compromising work responsibilities.A workcation does not require you to clear a solid block of time out of your schedule — you only need the ability to perform your tasks via the internet. You will still meet all your deadlines and answer your emails, but instead of doing them in the office, you can do them from the comfort of your second home or vacation rental. And your precious vacation days can still be used when desired.

Which jobs and roles are a good fit for a workcation?

Unfortunately, not every kind of job is well suited for remote work. If you work in a role that requires frequent in-person interaction with customers or colleagues, you may not be able to swing it. Similarly, work-from-home roles that require a lot of equipment may not be particularly suited for a workcation, simply due to how much packing and setup is required. Generally, people with office work, self-employed roles and those who already work remotely from home are the best candidates for a successful workcation.

Should you take a workcation?

A flowchart outlines the decision-making process for taking a workcation.
If you’ve never experienced the benefits of working on the road before, it can be difficult to finally take the plunge. A lot can be at stake if something goes wrong. Evaluate your workload to figure out if a workcation is right for you.

Questions to ask yourself

  • Do you have too few vacation days to make a long trip worth it?
  • Will someone cover your work responsibilities while you are away?
  • Does your work have flexible conditions?
  • Do you have a destination in mind that provides a reliable internet connection?
  • Will you be able to perform all of your typical work functions from this destination?
If you answered yes to those questions, then a workcation might be just the thing you need to squeeze more travel into your life.  

How to plan a workcation in 7 steps

A checklist lists seven steps for planning a workcation.
If you want to take advantage of all the benefits a workcation has to offer, then there are several steps you can take to maintain productivity. Establishing a routine and defining boundaries will go a long way toward keeping your days focused and your nights free. 

1. Schedule it in advance

Your boss is the first potential obstacle to making your workcation dream come true. Before you approach your boss, prepare your answers to any likely objections. Reassuring them that you will still meet important deadlines and be reachable during core hours during your workcation is crucial. When raising the topic, be direct. Tell them exactly what you want.
  • “I was wondering if I could work remote the week of ____?”
Tell them why you think it would be beneficial.
  • “I’ve been having a hard time concentrating in the office with so much going on. Getting away for a week would really help me get things done.”
Let them know you’re a team player.
  • “I don’t want to burden my team with my absence, so I’d rather continue working on [your big project].”
Tell them you've thought through the technology requirements.
  • “I’ve already used my work laptop to access our platforms from home without issue. And the house I’ll be in has dependable internet access.” 
Explain that you’ll still be reachable when needed, even if you’ll be in another time zone.
  • “I intend to be online during our normal working hours.” 
Even if you already work remotely full time, it is still a good idea to communicate your travel plans to your manager and co-workers. Letting them know in advance that you will be traveling is a good way to prepare them for any mishaps that may arise, such as a flight delay that strands you in an airport or a connectivity issue.  

2. Set a routine

If you’ve never worked remotely before or are only used to working in a specific location, a new environment can really throw you off. Reinstating a familiar routine can help you regain your bearings.The temptation to work in your pajamas may be strong at first, but try to avoid it. It’s important to change into day clothes to remind yourself that there is work to do. Save the vacation mindset until after you’ve clocked out for the day.Similarly, try to stay in a place that has a dedicated home office or a guest house. This ensures you have a quiet place to focus, and also lets you separate work and play time at the end of your work day.It can also be helpful to incorporate parts of your normal routine to your destination. If a cup of coffee or a big breakfast was a pre-work staple before, keep it going for your workcation. If a morning gym session helped energize you to go into work, keep exercising. You can even adapt your typical routine to this new location. For example, substitute your normal gym class for a run on the beach or a walk through town

3. Declutter physically and digitally

Space can be limited at a vacation property, but carving out somewhere for you to focus should be a priority even if you can’t track down a fully separate work space. Even setting up a corner of your bedroom with your work equipment can be beneficial. Wherever that space is, start by clearing out anything that is not conducive to a working environment. Remove the clutter that only serves as a distraction in your vacation rental. Once you’ve isolated yourself from physical distractions, focus on the digital distractions. Clean up your desktop from all of the loose files you have no intention of using. Delete emails that are no longer relevant so that you can quickly locate the information you need to do your job.

4. Define boundaries with colleagues

The demands of every position are different, but it is important for everyone to draw lines for when work does and does not happen. Well-defined boundaries can make for more productive workdays and help you avoid burnout — at home and during a workcation. Communicate to your coworkers when you will be online and when you’ll be at lunch, and resist the urge to answer messages outside of that window.An added complication of remote work is that it becomes mentally harder to take sick days. This applies to workcations, too. Often, remote workers will rationalize working through illnesses since they will still be home anyway. But taking breaks from work are important aspects of the recovery process.This goes for mental health days as well. If taking a day off can improve your wellbeing and future performance, you owe it to yourself to do so.

5. Define family boundaries

Family boundaries are just as important as co-worker boundaries. In fact, 38% of remote workers have trouble maintaining work-life balance. Working in a vacation home where families and friends have unlimited access to your attention is a temptation many people are unprepared for. That’s why it’s best to set these boundaries before you go on the trip. Tell them when you will be working and have a set plan for when you’ll be available.A separate room is ideal for family boundaries. Having a door to close and cut yourself off from distractions will send a clear message to your companions and help you focus on the work at hand. Save your socializing after you clock out for the day.

6. Schedule your free time

A workcation can quickly spiral out of control when you’re trying to please both your boss and family. Use a schedule to keep all of your commitments in order. But don’t forget to commit some time to yourself. This is your workcation. Making time for your hobbies and the activities that interest you helps make these trips worth it and makes you more likely to do them in the future. Doing what you enjoy isn’t selfish, as leisure activities are positively linked to mental health benefits. Get up early for a pre-work activity, visit a local spot for lunch or plan an activity at the very end of your day so that you can have a hard stop time. You might even consider tacking on a few days of PTO onto your workcation so you have more time to explore away from your desk.

7. Stay productive

Since one of the main reasons for your workcation is to experience what a new location has to offer, you’ll want to work efficiently so you can maximize your free time. Otherwise, you might as well have stayed at home. Aside from having a dedicated workspace, there are other ways to maintain productivity on a workcation.  
  • Implement the pomodoro time management technique. It avoids multitasking in favor of a single task and implements timed intervals. 
  • Check your email at dedicated times.
  • Block websites that only serve as distractions.
  • Set up templates for tasks that are performed regularly. Think about emails, briefs and spreadsheets that could be duplicated in advance and customized when needed. 
  • If your work doesn’t need to be done at a specific time, try waking up early when the rest of your family is asleep. 

Best workcation destinations

The ideal workcation destination will provide enough space and serenity for you to get your job done while also offering plenty of activities to make the workcation worth it. Here are four top destinations that make it easy to combine business and personal travel.  

Aspen, Colorado

Two people are hiking in Aspen, Colorado, one of the top workcation destinations in the U.S.
Nature lovers will have their hands full taking advantage of all that Aspen, Colorado has to offer. Known for world-renowned ski trails, this is more than just a winter destination. It also has hiking trails, mountain biking, a mountain gondola and more. Some of the hotels have workcation deals and special accommodations, such as extra computer monitors and internet connection boosters. 

Jackson, Wyoming

Downtown Jackson, Wyoming — a top workcation destination — sits at the base of a mountain.
Another city known for its amazing natural surroundings is Jackson, Wyoming. Surrounded by world-class ski resorts and national parks, there are activities year-round to be enjoyed after work. Even with these attractions, the city of Jackson still doesn’t betray its small town roots. But just because it’s small doesn’t mean it is behind the times. It still has all of the amenities a professional needs to get their job done, like office space packages and reliable internet.  

Miami Beach, Florida

Cars line the street and people walk in the sand of Miami Beach, Florida, one of the top workcation destinations.
Miami Beach has a surplus of sand and sun for those looking to bypass the four-season year. Take advantage of the ocean access by chartering a fishing boat, take an architecture tour of the distinct art deco buildings, or experience the nightlife by visiting the many vibrant dance clubs. Sunny work-from-home rentals will bring fresh energy to your normal day-to-day routine.  

Sonoma, California

Acres of grape vines grow in a field in Sonoma, California, a top workcation destination.
Looking for a middle ground between mountains and beach life? Take a tour through Sonoma to experience one (or more) of its many vineyards. Start the day off with a morning hot-air balloon ride and fill your evenings with a trolley, limo or bike tour. Sea lovers can take comfort knowing Sonoma has access to California’s beautiful coast. There are a number of travel packages available that make this location a great affordable option.  A workcation can open up new avenues for finding a work-life balance that was previously unattainable. Tailoring the destination and activities to your needs will ultimately help you decide how beneficial it can be. Explore your options for upgrading your vacations from rare to regular by purchasing a second home in your dream location.

Workcation FAQ

Why would you take a workcation instead of a vacation?

A workcation provides the opportunity for workers to travel without spending valuable vacation days. Those with limited personal time off can save it for unexpected emergencies and avoid the risk of missing important deadlines.

What if you work in a different time zone?

Work with your manager and co-workers to decide when you will be online ahead of your trip. That way, everyone will have realistic communication expectations, and any potential issues can be avoided.

Should I bring my family on a workcation?

So long as you have the necessary space and time to complete your professional commitments, bringing your family on a workcation can be a great way to create memories. Be sure to set clear expectations of family roles and responsibilities before the trip — especially if you’re bringing kids. 

What should you bring to a workcation?

Pack as you normally would for a vacation to that destination, and bring along your desired personal items. If this is your first workcation, overpack the items you’ll need to perform your job. Include anything you may need and may not have easy access to acquire at your destination, such as: 

  • Work clothes
  • Vacation clothes
  • Work computer with charger
  • Headphones
  • Daily planner
  • Toiletries 
  • Notebook and pen

An Infographic including a venn diagram and flowchart outlines when and how to take a workcation.

Ready to become a workcation pro?

If you end up loving the remote work trip life, consider making it a regular occurance. As a co-owner of a Pacaso second home, you’ll have ample time to enjoy your favorite destination each year, without having to stay somewhere new every time the workcation life calls you.

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