Setting up a yearly travel routine: A guide for remote workers

Whether you’re a freelancer or have a job that allows you to work remotely, depending on certain circumstances in your life (finances, family, health, etc.), you may be able to travel much more than your friends who work more “traditional” jobs.

I began working remotely in 2015, first for a company and then as a full-time freelancer. Though I am still constantly learning from my travels, I have found that I enjoy being based in a city and booking ~monthly travel, rather than being a full-time digital nomad. Having a base helps me establish better personal and business relationships and it allows me to focus more on my physical and mental health.

Regardless of if you’re a remote worker like me who prefers having a travel base or if you’re a digital nomad constantly on the run, you may benefit by establishing a yearly travel routine.

What is a yearly travel routine for remote workers?

Both to keep my finances in check and for business/health purposes, I try to limit my travel to around one trip each month (and yes, I know I am ridiculously lucky to have this ability). Assuming I’m able to accomplish this goal each year, this means I’m generally taking at least 12 trips each year.

Of those roughly dozen yearly trips, there are certain destinations that I will (almost for sure) visit. For me, they are:

  • Puerto Vallarta, Mexico
  • Medellín, Colombia
  • Scottsdale, Arizona
  • Los Angeles, California
  • Hawaii
  • New York City

I consider these destinations to be part of my “yearly travel routine,” which is basically a set of locations that I try to visit once each year.

Puerto Vallarta1
Puerto Vallarta, Mexico: one of my yearly travel destinations.

Why have a yearly travel routine?

Having a yearly travel routine is not right for everyone. If your singular goal is to see as much of the world as you can while you can, having a yearly travel routine could stifle your ambition.

But for many remote workers, setting up a yearly travel routine has a lot of benefits. Advantages to having a yearly travel routine include:

  • Having a base of friends/clients in the places you’re traveling to. As a remote worker who’s traveling, your days may often be spent on your computer, on calls, and away from society. After you get done working, you may be itching for human interaction, but may not want to put forth the effort to meet someone new. By traveling to the same locations each year, you’ll slowly get to know people, and can have built-in post-work and weekend plans.
  • Assurance that you’ll have working infrastructure. Before each trip I book, I do everything I can to make sure I’ll have the necessary tools (mostly, reliable WiFi) to work. But I’ve been unpleasantly surprised before, arriving at a location where the internet was subpar (or lacking completely). Two qualities my yearly travel destinations all have in common are great infrastructure and settings which are conducive to my remote practice.
  • Knowing how to navigate these locations. Something I love about travel is having new experiences. That said, there is something great about arriving in a city and already knowing where to find the things you need and like, like grocery stores and restaurants, and having a feel for the city’s public transportation system. This can reduce time spent trying to learn a city, can lower overall costs (like knowing where the cheapest place for a great, quick lunch is), and can reduce travel anxiety.
  • Knowing where to stay. One of my favorite parts of my yearly travel routine is that for each of these locations, I already have either set neighborhoods or locations that I like to stay in. Almost uniformly, I pick these places because I’ve stayed before, have had good experiences, they are conducive to remote work, and they reasonably priced. Trying to find lodging, especially for a remote work trip, can be stressful, so having set places to stay makes planning travel a lot easier.

How to choose your yearly travel routine destinations

Choosing your yearly travel routine destinations can be difficult. Below is a brief description of how I chose my destinations:

  • Puerto Vallarta, Mexico – Since I live in San Francisco, Puerto Vallarta is an easy (and often fairly inexpensive) flight away. My friends like to go once a year, and I’ve added myself onto their annual trip, usually around March/April. The weather is perfect around that time of the year and I can save costs by splitting my room/remote office with a friend who also works remotely.
  • Medellín, Colombia – Thanks to Copa’s direct-flight service from SFO to Panama City, South and Central America have become much easier to access from San Francisco. Medellín is a surprisingly easy flight, and it’s relatively inexpensive (for around ~$50/night, you can rent an apartment in one of the best parts of the city with an amazing view in a luxury building, and for ~$20-$30/night, you can still find some amazing deals). It’s also stunningly beautiful with a great freelance community.
  • Scottsdale, Arizona – Having gone to college in Arizona, I like heading back to Arizona at least once a year to see friends, and also to enjoy the weather and lying by the pool.
  • Los Angeles, California – Since I have many friends and clients located in the Los Angeles area, I usually need to go at least once a year for business or social purposes. But even if I didn’t need to go, I still would, as I love the weather, the hikes, and (for the most part) the people.
  • Hawaii – I don’t know if I’ll live in San Francisco or California my entire life, so I want to take as much advantage of being a 4-5 hour flight from Hawaii as I can. Also, having lived on Guam, I have a lot of friends that relocated to the islands, so I can often see them whenever visiting.
  • New York City – Growing up in New Jersey and having gone to law school in Philly, I have a lot of friends in New York City. In fact, my sister lives there and I also have clients in the region. While I am not generally a fan of the northeast, the people here make it worth a yearly visit.

As you can see, one of the main factors behind the locations I’ve selected is people. In making your list, you may want to base your yearly travel routine on seeing friends, clients, and family (especially those located in amazing places).

Scottsdale
Sunset from Scottsdale, Arizona

Another factor is reliable WiFi – every location listed above has an infrastructure that fully supports remote work. Similarly, each location above is located in a time zone that is conducive to my schedule. While I often take a few trips each year to time zones that are “difficult” to work from for me (such as Asia and Europe), my yearly travel routine is focused on destinations that I can work seamlessly from.

Something that’s also important in establishing your yearly travel routine is easy flights. Whenever possible, I like to fly direct, and with the exception of Medellín, I can get to each of these destinations directly from San Francisco.

Final tips for establishing your yearly travel routine

If you are a remote worker who is interested in establishing a yearly travel routine, I would recommend leaving room so that about half of your trips are to new (or rarely traveled to) destinations. Part of the fun of being a remote worker who can travel the world is seeing and experiencing new places. By visiting new destinations each year, you’ll be sure to expand your mind, you’ll likely have more interesting stories to tell, and you may even find new places to add to your yearly travel routine.

Are there places you try to visit every year? Let me know in the comments!

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