How to Plan a Trip as a Remote Worker

It’s been on your mind…that one place you really want to visit. Maybe you’ve seen photos, heard stories, you’ve pictured yourself going. You probably have it in your mind right now. If you are currently a remote worker, this post is your sign to take the trip to that place. This post is also a guide on how to start planning for it. 

Once you know where you want to go, here are some of the questions you’ll want to ask yourself. 

When to travel? 

If you’re traveling internationally, be sure to check the weather year-round and find the time with the climate you’ll enjoy the most. This tip comes especially from personal experience. The very first solo trip I did was to Bangkok Thailand…in the middle of Monsoon season…and no I did not check the weather beforehand and yes a monsoon hit the first day I arrived 😅 Sure it makes for a fun travel story but just be sure to check the weather conditions. 

Where to stay? 

This part gets fun because there are so many different types of travelers. 

Hostels: 

You might be the solo-backpacker type. In this case, I might recommend a hostel so that you can meet other travelers, many of whom are also traveling on your own. Most hostels offer both shared and private rooms. The downside of a hostel is that you don’t typically have as much space and it can be tough to find a dedicated work area, however, you can always find a local coworking space instead. 

Airbnb:

Whether you are a solo traveler or with friends or as a couple, Airbnbs are always a good way to go. Offering so many different options in most cities around the world Airbnbs make great accommodations because you have more space, typically a kitchen, and it can double as a workspace. The two potential downsides of Airbnb are the occasional cost (though in some areas around the world it’s incredibly inexpensive) and it’s a lot harder to meet other travelers. Tip: Booking a private room in someone’s home could be a great way to meet some locals!

Hotel:

Surprisingly, hotels aren’t as common in the digital nomadding / remote worker community. Hotels can be great because there are often basic amenities provided, housekeeping, and it typically comes with the feeling of safety. With a hotel room though, you are pretty secluded in your own area, so it’s helpful to find a coworking space or other activities to meet locals or other travelers. 

Resort:

Staying at a resort is for the traveler(s) who want to indulge in lots of amenity options. Typically with a resort, you’re paying a lot more, but you’re doing so with the assumption that you’ll likely be staying there most of the time. Often times, a resort is the best option for a vacation where minimal work will be involved.

Where to Work?

I touched on this a bit in the above but you’ll likely have a few different options for where to work. If you’re staying in a spacious place then you might find a convenient workspace in your temporary home. If this isn’t doable, for example, if you’re in a smaller airbnb, hostel, or hotel room then there are tons of other options.

Many of the options will depend on the city you’re visiting. For example, if you stay at a hostel that is specifically for digital nomads, like Selinas, many of these have a dedicated coworking space, but Selinas is mostly in Central and South American countries.

Another widely used option is WeWork. A popular coworking space, known for its aesthetic features and cold brew on tap, this is a great place to spend your working hours where you’ll meet other remote workers who are traveling or locals. WeWork is mostly in the US or Europe, so you’ll want to look this up beforehand. A simple Google search for Coworking spaces in [insert country you are visiting] will likely produce a few results. 

Another option to find a place to work is local cafes. This is a great option because you get to work and experience some of the local cultures- whether it be their coffee and food, cafe conversations, or whatever you encounter to and from the cafe. One thing to note is that you’ll want to scope out whether they have WiFi beforehand. Tip – to get to the cafe a bit earlier before you start your work in case you need to go with a backup option. The reason for this is so that you can get a feel for the cafe environment (noise level, wifi speed, and general ambiance) before you begin cranking away. 

What to Do? 

The most significant aspect of working remotely while you travel is to experience the new sites around you, of course! While we are there to experience working in a new environment, it’s important to remember to go out and explore it as well.

Some ideas for what to do when you’re in a new city: 

San José De Maipo, near Santiago Chile

  1. Visit the best local restaurants in the area. Steer clear of the heavily touristy areas as you may not get the same experience. Try out the smaller mom-and-pop restaurants, the local bakery, or cafes. Make sure to try what the city or country is most known for. I had so much pasta in Rome and fried rice in Thailand and it was worth it! 
  2. Go on some adventures and take some risks! Let’s be honest, if it’s the first time you’re traveling as a remote worker, that can feel risky and scary to some. So why not lean into that? Go ziplining in Monteverde Costa Rica, take a surf lesson in Canggu Bali, and drive some UTVs through Moab Utah – you can do it! My favorite place to book these types of adventures is through Airbnb experiences or by googling it and finding one of the local excursion businesses.
  3. Talk to locals. This one might be tough, especially if there is a cultural or language barrier. However, most locals are more than happy to talk to travelers, as long you’re respectful (though I think that’s a given). Start by taking the opportunity to chat with locals when it’s convenient- the cafe barista, the store clerk, or the tour guide. Starting conversations with the people you meet where you’re staying or working is another great way to connect with locals and/or other travelers. 
  4. Don’t pass up the landmarks. Sure, maybe your instinctive thought is that these are tourist traps, but they are famous landmarks for a reason. If they are historical or meaningful to the place you’re visiting, it’s a good idea to check them out. 
  5. Explore the city on foot or by bike. While ubering is very common in most countries now, you just don’t experience the city the same way. Walking the town is not only a great way to get your steps in (especially if you’re out of your typical fitness routine) but you get to see sites you wouldn’t see through a car window. Biking, scootering, or other modes of transportation outside of a car are going to create better experiences because you’ll see the city more through the lens of a local. For example, in places like Amsterdam, biking is almost more common than walking. In Bangkok, people take Tuktuks everywhere. Give it a try!

These are some helpful tips for traveling as a remote worker. These tips are based on three pillars of travel I love to live by: Work, Community, and Adventure. Engaging in activities that involve these three will create a memorable travel experience. And who knows? You might just catch the travel bug and continue to do your remote work while traveling the world. 🌎

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