Lessons Learned from My First Working Vacation

I’m a strong advocate for leaving your work at home during vacations. However, with the rise of remote work, the possibility of a working vacation became an appealing option for seeing the world while still preserving PTO. With that in mind, my partner and I recently decided to take our first-ever working vacation. If you decide to take your own working vacation, here are some issues to consider before you go for it.

The first two items are the most important. The next few things aren’t necessities but can make the experience more convenient or enjoyable.

Good Wi-Fi

Good Wi-Fi is important for any remote job. When looking at lodging options, first ensure the place has Wi-Fi. After doing so, make sure to scan the reviews for mentions of Wi-Fi performance.

A Comfortable Place to Work

You might be used to a nice setup at home, so you’ll probably need to lower your ergonomic expectations when searching for places to stay. That doesn’t mean you need to settle for a couch or a stool, but it does mean you will need to compromise. Keep your eyes out for a picture of a desk when browsing websites for your lodging options. If a desk isn’t available, a kitchen table is also a decent option!

A Kitchen

When you’re in a new area, you’ll probably want to enjoy some local cuisine. However, costs can add up if you go out for every meal. Having a kitchen can help alleviate that by allowing you to buy groceries and cook your own meals.


If you’re like me, you like to pack light. If the place you’re staying has laundry, it allows you to pack even less stuff since you can clean your clothes on site.

Luxuries You Don’t Have at Home

While not completely necessary some amenities you don’t have at home can make a working vacation much more enjoyable. On my recent trip, the place had a hot tub that we used almost every night. If you’re staying somewhere that isn’t your home, you might as well get some added enjoyment!

An Early Wakeup Time

On normal vacations, I take advantage of the fact that I can sleep in. However, on my last working vacation, I tried waking up a few hours earlier than normal so I could stop working earlier in the afternoon. This allowed us to use more time in the afternoon for exploring the place we were staying. In our case, we stayed in Joshua Tree, so we filled our afternoons with hikes.

The Case for a Working Vacation

Now that I know it’s an option, I can see my future involving more working vacations. Exploring new areas, while still saving my PTO for more exciting locations is something I would love to continue doing.