I’ve Been to 54 Countries—Here’s How to Pick One to Work Remote From Abroad

I may have a laptop and a job I can do remotely, but that doesn’t mean I can work from anywhere. I learned the hard way trying to connect to Zoom from Montezuma, a tiny bohemian beach town on the southern edge of the idyllic Nicoya Peninsula in Costa Rica.

It wasn’t until we settled into our dreamy Airbnb with its expansive veranda and ocean views that I realized just how difficult it was going to be to work from this paradise. While there was Wi-Fi, internet connectivity was spotty and Zoom calls were almost impossible.

I’ve been to 54 countries and counting, and I’ve been combining business and leisure travel for as long as I’ve been working. But I’ve changed my approach to remote work since that Costa Rica trip. Instead of figuring it out when I land, I now ask myself these questions before I take off:

I may not need a desk or office of my own to get my work done, but I do need a strong Wi-Fi connection. So I look for remote work destinations with fast internet speeds. Speed Test, a tool for checking internet speeds, maintains an index of countries with the fastest connections. I make sure any lodging I consider has Wi-Fi and read all the customer reviews I can find that mention the Wi-Fi before booking. Places that offer free public Wi-Fi or are home to lots of hotspots like internet cafes get bonus points.

I’ve been traveling to India my entire life, and I know just how frustrating it is to have the power go out when you’re trying to work. It’s not uncommon for the power there to be out for several hours a day and it always seems to happen when your laptop is dying and you have work to do.

For people whose laptops are their professional lifelines, India, Costa Rica, and any other destinations where power outages are common can be tough to work from. The World Economic Forum maintains a list of countries ranked by the reliability of their electricity.

Some people are willing to wake up at 2 AM to start their workdays and collaborate with team members in different time zones. I am not one of them. I look to work from places that are within a reasonable time difference.

Most of my clients are in the U.S. So if I’m in Europe, I can enjoy the day before the U.S. gets online and plan to work in the evenings. If I wanted my evenings to myself, I’d consider remote work destinations in Central America, South America, the Caribbean, and Mexico.

Some countries are particularly friendly to remote workers. Estonia led the way in welcoming digital nomads when it became the first country to officially roll out a digital nomad visa in August 2020. It allows remote workers to live and work in Estonia for up to a year. Without the visa, U.S. citizens would have to leave after 90 days. Iceland, Barbados, Anguilla, Dubai, Antigua and Barbuda, Bali, Bermuda, Costa Rica, and other countries have introduced similar programs. Before you pick a destination, check with local immigration offices to find out if you’ll need to obtain a visa to work there legally.

And don’t forget to research destinations to find out about any dealbreakers like laws that may endanger LGBTQ visitors.

Having time to both work and enjoy the place you’re working from requires slowing down. To accommodate longer trips without blowing my budget, I book longer stays in more affordable remote work destinations and spend less time working from more expensive places.

As much as I love Iceland, for example, its high prices for food and lodging make it a far more expensive remote work destination than, say, Portugal or Estonia, where a lower cost of living makes it easier to budget for longer trips. For longer stays, I also look for accommodations with kitchens or kitchenettes so I can save money by making at least some meals at home.

I know myself well enough to know it’s harder for me to work from cities like New York, Paris, and Amsterdam where there are seemingly endless distractions.

Before I began working remotely, I wouldn’t have been excited about an all-inclusive beach resort in an area without much else to do. But I’ve come to appreciate slower-paced places where sitting in front of my computer is less likely to make me feel like I’m missing out on something else. And after sending emails from a hammock in the Dominican Republic, I’m not sure I’ll ever go back to traditional office life.

If you’re trying to figure out where to work from, these are a few of my favorite digital nomad destinations:

• Portugal: Portugal is more affordable than many other European countries, boasts 300 days of sunshine a year, and is just five hours ahead of New York City. Madeira, an autonomous island region of Portugal, has built a digital nomad village that offers visitors free coworking space, help finding accommodations, and entry into a community Slack group.
• Estonia: If you’re looking for charming historic streets, high internet speeds, and a low cost of living, look no further than Tallinn, Estonia’s capital. This is an excellent home base for exploring Scandinavia and the Baltics on the weekends, and Estonia’s digital nomad visa allows location-independent workers to apply to live and work in the country for a year.
• Iceland: Iceland is just a short, nonstop flight away from cities including Denver, Chicago, New York, and Boston. It’s an expensive country but one that offers a priceless opportunity—the chance to experience Icelandic hospitality while working against a backdrop of volcanoes, glaciers, and epic lagoons. Iceland’s remote work visa is valid for up to 180 days but requires applicants to make about $8,000 a month to qualify.
• Panama: If you want to be fooled into thinking you’re working from Jurassic Park, head to Panama. This Central American country is rolling out the welcome mat for remote workers with a short-term visa that allows visitors to stay for up to nine months while working for foreign companies or as freelancers with clients abroad.
• Dominican Republic: The lightning-fast Wi-Fi and onsite coffee shop at the TRS Cap Cana in Punta Cana—where I wrote my first draft of this article—made me feel like I was at a luxury coworking resort. All-inclusive resorts like this one make it easy to balance work and play in a place where my dollars go far. If I’m going to be stuck in front of a screen, this is somewhere I can do it while watching palm trees sway and enjoying the island breeze.