Freelancer Tips

How to Pick the Right Places to Travel as an Anywhere Worker

Alisa Kellam
August 7, 2023
Anywhere Worker

Where would you go if you could go anywhere in the world?!

I’ve both posed and answered this question numerous times over the years! Little did I know I would win a contest that gave me the opportunity to do so with someone else picking up the bill!

Upon learning that I was one of the lucky Fiverr freelancers selected in the Anywhere Worker contest sponsored jointly by Fiverr and Selina Hostels - insert much excitement and celebration here! - I started out by talking with friends and family about where they would go if presented with such an opportunity. I received countless great ideas from others. Some would go to faraway cities long dreamed of, landmarks yearned to see, and once-in-a-lifetime experiences desired.

While I would have loved to travel to Thailand or Australia, I made my decision on the country to visit using the following three high priorities. I then narrowed my city choices based on a handful of other factors. The top three priorities for me? Staying in a time zone shared by the United States, wanting to visit a country I had never visited previously, and, of course, fast, reliable wifi

Staying in a time zone shared by the United States.

My business coaching clients and online learning students are primarily in the US so traveling to a time zone that coincided with the United States work day was a top priority. Of course, this isn’t a consideration for everyone. About a decade before covid changed our lives, my brother became the first digital nomad I knew! He had the good fortune to work remote for an employer who only required him to have a dependable internet connection, make it to meetings, and complete his projects on time. He traveled the world during that time and I longed to do the same!

Desire to visit a country I had never visited previously.

I chose to travel to a country I had never been to previously. While there is much more of Canada and Mexico I have yet to see, I have been to both countries previously. Some may prefer to travel to a country they have an affinity for and a level of comfort with. My preference was for the unknown. Given my top priority of staying in a US-friendly time zone, I narrowed my country search to those in Central or South America.  

Needing fast, reliable wifi.

My Anywhere Worker experience enabled me to stay at any Selina Hostel in the world for 3 weeks so in many ways my decision was made. Selina is known for their CoLive program, which promises digital nomads the ability to work and live in hostels around the world. While speed can vary based on country infrastructure and property type, internet service worked great at the four locations I visited around Costa Rica.

Other considerations in deciding where to travel.

Language. While I love traveling to new countries, I also value the ability to communicate. I did have a working knowledge of Spanish after 3 years studying the language in high school and a recent refresher in preparation for a trip to Mexico. My familiarity with Spanish confirmed that traveling to Central America or South America seemed like the right choice - and my motivation for getting going on daily Duolingo practice!

Safety. Understandably safety fits into the equation when deciding where to travel. For those from the United States, I recommend checking for travel advisories early in the process.

Cost of living and exchange rate. As I researched different countries, I evaluated both the cost of living and the exchange rate in relation to the United States and the US dollar. While it wasn’t a top priority, it was helpful to know when selecting cities.

Experience desired. There are cities one visits with a checklist of landmarks to see, museums to tour, and fine cuisine to savor. At this point in life, I opted for a ‘being’ experience. Since covid entered our lives in early 2020, I’ve changed jobs, moved to a new city, become an empty nester, and experienced relationship changes. I’m sure I’m not alone in my readiness for a restorative and relaxing experience in a beautiful country. Costa Rica with its Pura Vida approach to life seemed a perfect choice.

Cities and hostels. Since my Anywhere Worker package involved staying at Selina locations, I consulted the Hostelworld site for reviews. The site was a wellspring of valuable information with ratings on Security, Staff, Cleanliness, Value for Money, Location, Atmosphere, and Facilities.

So there you have it, that’s how I chose where to travel for my 3 weeks as a digital nomad! In the end, I chose San Jose for a city experience, Manual Antonio for a beautiful location near the ocean and national park, Santa Teresa for a beautiful beach and nature tours, and Monteverde for a cloud forest hiking and ziplining experience.

Alisa Kellam
Ailsa is a business coach, content creator, and traveler. She is an innovative, collaborative, and action-oriented leader with an entrepreneurial mindset and a passion for learning. She is excited about the intersection of digital marketing, learning, and content creation, and is interested in partnering with organizations and individuals to create digital learning solutions and build inclusive communities. Her background includes 15 years of experience in a variety of business leadership roles and 9 years of experience creating and delivering learning content. Over the past four years, she’s been a digital nomad and created content from international locations. Instagram: @ailsakellam
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