Visualy ®

How to Plan a Workcation With Your Friends

April Zimmerman
ABOUT THE AUTHOR

Our group circled around and listened as the guide explained safety instructions. “Float on your back, keep your nose and toes above water, and do not stand up in the rapids.” For a few of us, including me, this was our first whitewater rafting trip. We slid our raft into the Savegre River and piled in. Bryan up in the front, Fred and I in the middle, and our guide in the back as our rudder.  Last spring, after a year of COVID surges, shutdowns, and new normals, my partner Fred and I landed in San Jose, Costa Rica with four friends. The six of us—one writer, one web designer, one project manager, two web developers, and one consultant—loaded into two rental cars and drove three and a half hours south to Uvita. We were there to work but we were also on vacation.

Many people choose remote work for the ability to create environments conducive to their personalities, workflow, and creative needs. Most of our group were remote workers before the pandemic, so we jumped at the chance to gather our long-distance friends and set up shop in a jungle-inspired location for a week. To garner rest, adventure, and togetherness, a workcation with your friends is an excellent idea—but it does require a lot of planning and consideration.

Invite People You Want to Be Around

It sounds like a no-brainer, but invite people you actually like. You will wake up and go to sleep together every day. You’ll share breakfasts and lunches and dinners. You’ll share living spaces and workspaces. You’ll navigate around each other’s meeting schedules and daily routines. You must vibe and communicate well with your travel companions. All but one of us had even collaborated on projects together before, so the six of us were familiar with each other’s workflow, personalities, and routines.

Calculate the Time Difference

If your job requires you to be online at certain times of the day, it may be best to choose a location close to your usual time zone. Everyone in our group traveled from the east coast of the U.S., so the shift from EST to CST for a week didn’t disrupt our work schedules. On the contrary, we woke up earlier, finished our work sooner, and had more time to explore in the afternoon.

Choose Accommodations With Plenty of Space

Ensure that there are plenty of workspaces—couches, countertops, desks, separate rooms—for everyone by getting a thorough visual of the hotel, home, or Airbnb where you plan to stay. If you’re not sure, ask the host to send additional photos. Our Airbnb in Uvita had a generous outdoor seating area and a large outdoor dining table that served as our home-away-from-home office for most of the day. When we needed privacy for meetings or calls, we retreated to the living room or a bedroom.

Check the Wi-Fi

Ask your host to complete an internet speed test before you book. Fast, reliable Wi-Fi is a must for your workcation, especially if you will be sharing the network with other people. You don’t want any surprises here and neither does your boss or clients. I recommend speed.cloudflare.com (“for the nerds,” my partner says) or speedtest.net.

Plan for Meals and Groceries

Research restaurants, takeout, and grocery store recommendations in the area. If you plan to cook, choose meals with basic ingredients and prepare to substitute or adjust meal plans based on what is locally available. Produce, herbs, meats, oils—all of these vary widely by country. Our Airbnb offered private chef services which we booked for two nights of our stay. Between six people, it was affordable and gave us the chance to try delicious local produce and cuisine. 

Respect the Country, Culture, and People

Try to assimilate to the local culture, not impress your own. Accept how things are and come prepared. For example, automatic cars are not common in Costa Rica and not everyone in our group could drive a stick shift, so we made a plan to rent one automatic and one manual car. Because we prefer to travel off the beaten path and we were traveling to places where English is not widely spoken, we studied common greetings, questions, and phrases.

Plan Time to Explore and Relax

The point of a workcation is to change up your surroundings and gain inspiration, so don’t miss out on the chance to explore a new place. During our week in Uvita, we went white water rafting, visited the Parque Nacional Manuel Antonio, hiked to Nauyaca Waterfall, and enjoyed poolside dinners, and evening swims—all while staying on top of our work.