5 differences between working remotely and going on vacation

While it is true that I travel a lot, I almost never take a vacation.

Because of my business as an attorney, I need to, at the very least, be accessible to my clients and engage in some kind of work wherever I go.  Despite all my travel last year, the only true vacation I took was to Palawan in the Philippines, and that was forced on me by staying in a village without any reliable WiFi.

After having just returned from an amazing South America trip, which took me through Colombia and Chile, I’ve been thinking about how working remotely differs from taking a vacation (aside from the obvious factor of having to work!).  Here are the top 5 ways the trips differ:

1. Reliable WiFi is key

The number one factor that dictates where I travel to is whether there will be reliable WiFi.

As a digital nomad, I can travel and work from virtually wherever I want, so long as I have steady access to reliable WiFi.  In terms of reliability, I need a connection with fast download speeds, that’s strong enough that I can have a call through Google Voice on it if need be, and where I can access the WiFi at all times from anywhere I am staying.

It’s often hard to determine places that will have great WiFi.  I’ve stayed at 5-star hotels with bad service and I’ve stayed in Airbnb’s in remote locations with strong signals. One way to ensure that you’re traveling to a place with strong WiFi is to stay at a place with reviews on TripAdvisor, Airbnb, or the like that mention a strong internet connection.

It’s also likely that more developed countries/cities, places with a large number of digital nomads, and touristy places will have better WiFi.  This isn’t always true, though – I recently was at a hotel in Santorini that had awful WiFi, despite me having no issues anywhere else on the island.

When I book real vacations, I am much less concerned about having reliable WiFi (and sometimes would prefer going without it).

2. Need to stay in one location for longer

When I travel for pure enjoyment, I usually like to bounce around a lot. I’ll often get to a city, stay for a night or two, then wander to a new location, and keep doing this until I have to go home (except if I’m relaxing on a beach somewhere, in which case I usually don’t mind staying put).

But when I work remotely, I realize that most days spent traveling are days in which I can’t work. On my recent trip to South America, I really wanted to check out Valparaiso in Chile, and even to head down to the Lake District. But because I had just bounced between Cartagena and Bogotá, I knew that it mean I’d have to stay put for a few days straight, and I ruled out any side travel from Santiago.

When you travel and you’re working remotely, depending on your business, you want to make sure that you’re spending most weekdays in one location, and limiting to travel to times when you wouldn’t otherwise be busy working.

3. Determining activities based on time difference, length, and accessibility

When you work remotely, you still want to experience the location you’re in. Sometimes this means doing something “touristy,” like booking an excursion, or going on other adventures.

When looking for activities, you want to make sure the length is only for a few hours (instead of for the full-day), that the activity doesn’t need to occur when you need to be working, and that you’ll have access to your phone and e-mail if you need it.

For example, I was recently in Belize and wanted to experience the snorkeling around their famous barrier reef. In picking a tour (full-day v. morning v. afternoon), I decided to go with an afternoon tour because my mornings were busier than my afternoons at that time, and I couldn’t justify taking a full-day off from work, despite the amazing tour itinerary.

4. Look for different types of rooms

Some friends who travel with me call me “Princess,” but I don’t mind. I love things like comfortable beds, hot baths, and great service.

In booking travel for remote work, I still look for all of these things, but something that is noticeably different is that the type of room I look for changes. For instance, on a typical vacation, I would be fine with a room that’s basically a studio, with only a bed, TV, and a very small desk.

When working remotely, though, that type of setup would not work for me.  Generally, I like some separation between my sleeping and working area, and I like places with large enough desks for me to have my laptop and at least a notebook and some papers comfortably next to me.  Additionally, I like finding places that have kitchens, so that I can cook food for myself, as venturing out for lunch in a new city/country can take a lot of time.

The places I get when working remotely are much more like apartments than hotels.

5. Views matter more

If you’re traveling to a new location and are working remotely, you may not leave your place much during the day. One trick to still enjoying your new location is to try and grab a place with an amazing view.

During a trip to Medellín, Colombia last year, I had so much work that I was pulling 10-15 hour days every day of my trip.  Luckily, I snagged an Airbnb with this amazing view.


When I think back to that trip, even though I barely left my apartment, I think about it fondly. That view was amazing, and I can’t wait to go back and experience it – and the city – again.

4 thoughts on “5 differences between working remotely and going on vacation

  1. Yeah, if work involves being connected to the grid then reliable access to the web not just essential but critical. And yes we too cannot live without what we would define as necessities – the clean and comfortable bed etc…lol


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