How We Traveled as a Family for 2 Years in Latin America, While Working 8 to 5

If someone would tell me a few years ago that I would travel for 2 years with my wife and our preschooler in Latin America, all the way from Mexico to Patagonia, I wouldn’t believe them. That’s just not something we planned, or even dreamed about.

Back in Israel I had a normal office job, Oxanna spent most of her time taking care of our toddler. Family, friends, an apartment, a car and a never-ending list of todos and errands. In short, all the niceties and trappings of a regular life. At the time, I couldn’t even fathom the possibility of a long-term family traveling. But sometimes life has a funny way of bringing you that which you can’t even dare to imagine.

Discard With Your Normal Life In Two Steps

Then, somewhere in 2015 we decided to move to Canada. Two years earlier, a close friend has moved to Toronto and planted the idea in my head. Peaceful and immigrant-friendly, Canada has been an attractive destination for Israelis for some years. After living in Israel most of my life, the idea of experiencing something new excited me. And Oxanna, being true to her Mongolian ancestry, is always ready to pack and move without too much deliberation.

To make the landing in Canada easier, I decided to find a remote job while still in Israel. Software development is one of the most remote-friendly occupations, but I’ve never worked remotely before, so I wasn’t sure how it would turn out. The only way to know is to try.

Summer in Vancouver. Multicultural festivals. Biking in the city. Hiking in the woods. But soon the summer was over and autumn covered the city with shades of grey. In November our 6-month rental contract was coming to an end, and with it came the realization that nothing really kept us in Canada at that point. We haven’t yet accumulated much stuff, our belongings were still fitting in 4 suitcases with which we landed. My work required me to stay close to the Atlantic time zone, but it didn’t mandate any specific latitude. So why not pass the winter somewhere warmer?

Baby steps. How do you begin a two-year trip around the continent? By telling yourself you are just going for a month.

But where do you go, if you know almost nothing about Latin America? Costa Rica? Panama? Eventually, the choice – made mostly by our cat, fell on Mexico (true story that will have to wait for another occasion).

Hello, Latin America

Our airport taxi was speeding through the night streets of Guadalajara. The basic Spanish I picked up from a Duolingo course was just enough to ask the driver about the best Tequila in Mexico. That pretty much summed up my knowledge of the Mexican culture at the time. I don’t think I understood his answer, but I remember the emotion that engulfed me that first night in Mexico. The feeling of suddenly standing on the verge of a new world, of which I knew very little. The intoxicating aroma of a big unknown waiting for us.

Our first days in Guadalajara. That sense of opening a door to a new world was intoxicating
“Danza de los Voladores”, an ancient Mesoamerican ceremony performed in Lake Chapala, near Guadalajara

We rented an AirBnb apartment in Americana, a trendy neighbourhood boasting eclectic architecture and hipster-friendly coffee shops. The landlord – a young, middle-class woman welcomed us in the apartment. Two questions were on our minds: where is the closest supermarket and whether she can recommend an English-speaking nanny.

Supermarket is easy. Take an Uber, pay with your regular credit card and fill the fridge with your favorite comfort foods. What else do you need to feel good in a new city ?

And the next morning a tall young woman knocked on the door. Our landlord’s cousin came to play with Ayan.

And so, during the next weeks a tentative routine has formed. In the morning I would go out to work in a cafeteria, while Oxanna would stay home with Ayan, studying during the morning “nanny hours”, keeping him busy in the afternoon. Evenings we would go out together exploring the neighborhood or just take Ayan to a playground. Pretty ordinary weekdays were compensated by action-packed weekends, exploring the city and taking day trips to nearby destinations.

Ayan with Sabina, our nanny in Guadalajara. She stoically endured the worst displays of a 3-year-old’s temper

That’s not a vacation. Not a gap-year traveling. Two-thirds of your time is filled with a regular, non-exciting life. But for someone who wants to travel as a family while working, this semblance of a routine combined with “weekend traveling” is probably the best possible arrangement. And truth be told, even the “regular life” is still pretty special. Because every routine errand, be it a pop into a supermarket or a stop in a pharmacy, is filled with discoveries. For someone dreaming of tropical beaches, that may not sound very appealing, but for us, immersion in a city life brimming with different culture, language and people turned out to be half the fun.

Even routine errands, such as shopping, are pregnant with discoveries. This Guadalajara supermarket had 5 kinds of nachos to try, and packaged maize kernels for the pozole soup (which in pre-Hispanic times was served with human flesh)
Dinner in La Chata, a popular local eatery in Guadalajara. Ayan quickly grew to love tostadas
Weekend-traveling in Tequila, the birthplace of the national Mexican drink

A New Home Each Month

A month and a half in Guadalajara turned into half a year in Mexico. Merida, San Miguell de Allende, Guanajuato, Mexico City. Spending about a month in each city, we traveled the country from the agave fields of Jalisco to the tropical jungles of Yucatan.

We soon discovered that a month is good default when planning how much time to stay in one place. It gives you enough time to explore the region on the weekends while maintaining a sane family routine. There is also a pragmatic consideration to staying at least a month in the same apartment: landlords on AirBnb give their maximum discounts on monthly rentals.

In every city we would find an English-speaking nanny, either in a Facebook group of local expats or through a landlord (which almost always has a cousin or a niece looking for a short-term job). We would use Uber for short commutes in the city, inter-city buses for weekend traveling and planes to move from one region to another.

Ayan with Laura, our Italian nanny in Merida

Since the cost of living in Mexico and most of Latin America is significantly lower than in North America, you don’t spend more than you used to, despite the frequent travel expenses. A furnished two-bedroom apartment in a good neighborhood usually doesn’t cost more than $1000 USD. We often rented good-enough apartments for $750 a month.

You have to be somewhat flexible and unfussy, because rental apartments will always lack something you need. That one doesn’t have a microwave, in another the kitchenware has no deep bowls for soup, in third one they forgot to put a door in the bathroom (that last one really happened). The point is, you have to learn to accept that some things will make you uncomfortable. But I can save you at least one small trouble right now: always bring a vegetable peeler with you. You always need it, and it’s never there.

Our AirBnb apartment in Merida used to be a lawyer’s office. When we arrived, the place didn’t have beds – the owners assumed we will be OK sleeping in hammocks. But the floor tiles in that place were gorgeous.

The upside is, the discomfort won’t last long, and will hardly matter. Thirty-forty days will pass, and you’ll be looking out through the window of your speeding taxi at the now-familiar streets gliding by, feeling bittersweet. Grateful for the people you met and the stories you heard. Sad that in all probability you’ll never return here. And strangely relieved to once more leave everything behind, and start from a blank page in a new place.

A weekend trip to Chichen Itza. Ayan was inspired to try and build his own pyramid.
A weekend-trip to Izamal, the yellow city of Yucatan
The last day in Merida, which for a month and half was our base in Yucatan

1 Month => 20 Months

Half a year passed, and we had to make a decision. Do we come back to Vancouver, do we stay in Mexico, or do we go on? Vancouver, with its high daycare costs wasn’t an attractive option. We fell in love with Mexico, so staying longer was definitely an idea we entertained. But we also wanted to discover other places, other countries. And so we decided to go on. Without planning far ahead, thinking just about the next month or two, we got a ticket to Nicaragua.

Ayan with his nannies in Lima, Valparaiso, Medellin, Merida, Santiago, Quito, Cusco and Arequipa

And so we went on. Exploring Central America, we spent a month in Nicaragua and another in Costa-Rica. Then we stayed almost 5 months in Colombia. We’ve become tired and wanted to stay in one place for a while, and so Medellin has become our refuge.

Around that time, a year into our trip, we realized it’s time to expose Ayan to Spanish. I was concerned he would forget English which he picked up in Vancouver (we speak Russian at home), without really learning Spanish. But turns out, I underestimated child’s brain’s ability to learn languages. Sarah, our beloved half-British, half-Spanish nanny from Nicaragua came to Medellin at the time, and has become Ayan’s first Spanish teacher. After her, we no longer searched for English-speaking nannies. A few months later, he was forming complete sentences and conjugating verbs.

After traveling in Colombia and staying put in Medellin, we crossed the equator (for the first time in our lives) and spent time exploring Galapagos islands and Ecuador. Then 3 months in magnificent Peru. The Southern Cone followed with Chile and Argentina. And finally, when we thought we saw it all, Brazil showered us with a whole new palette of colors and sounds.

What started as a one month stay in Guadalajara has become a 2-year journey in 9 countries. Dozens of cities, hundreds of plazas, churches, museums, pyramids, national parks. And most importantly – friendships, people, their stories and songs. An unplanned, almost accidental trip has turned into the biggest adventure of our lives.


Those first few weeks in Guadalajara were exciting. New sights, new smells, making the first connections with locals. Surrounded by friendly and courteous people everywhere, the fear has soon waned and turned into a sensible precaution. Everything was great, or so I thought. And then came the crisis.

“Let’s go back, I’ve had enough of this life”, Oxanna told me one day after about a month in Guadalajara. “We don’t know anyone here, we have no friends. Ayan is throwing tantrums every day, our poor nanny doesn’t know how to handle this, and I don’t blame her”.

While my daily life had a schedule and structure, and was partially isolated from the whims of a moody toddler, Oxanna’s was exposed to it. А life on the move comes with obvious perks, but it also has its share of hurdles. Without the usual support networks you had back home, the increased demands of childcare taxes your emotional resources and tests the resilience of your relationship.

Constant changes and adjustments are part of the deal. The toddler is bored home? So how about sending him with the nanny to the park or the museum? (Do we trust her enough for that?) Maybe we need more toys? Maybe I could (should) spend more time with him then I do? Maybe he is old enough for a gentle kindergarten? We would return to this conversation time and again during our travels. There are no magic solutions. Each child requires a different approach. And each family has to find its own balance.

“Spiral Garden”, a free-spirit daycare run by an American family in Colon, Costa-Rica. During our month in Costa Rica, Ayan spent the mornings here.
Saints and virgins keep children a company in this kindergarten in Medellin. Despite staff’s efforts to accommodate us, after a trial week we took Ayan out. It had too much discipline, and too little free play.

We also realized we have to meet people. Loneliness isn’t a problem when you travel as a family, but isolation is. To feel more connected to the places and people around us, we would make an effort to meet locals as well as expats in every city we stayed.

Two good platforms to meet people when traveling are Couchsurfing and Conversation Exchange. Couchsurfing used to be our favorite – after all, me and Oxanna met in a Couchsurfing party, years ago. We still love it, but you’ll mostly meet younger people through CS. Conversation Exchange on the other hand allows you to meet locals that would like to learn English, and in turn are willing to help you out with Spanish. Those often turn out to be people in their 30’s and 40’s that are studying English either for job or immigration purposes.

Celebrating my birthday with Couchsurfing friends in Guadalajara
Traveling in Izamal with our new yucateco friends

Working on the Move

People ask me sometimes, “but how did you manage to work, while constantly moving?” The truth is, working was the easy part, it’s the traveling part, that was exhausting. Often times, after another intense weekend of sightseeing, I would open my laptop on Monday morning and feel happy that I can just dive into familiar work, and let my mind and body rest from that incessant stream of experiences.

Working in Miraflores, Lima, with a view on the Pacific ocean
A view from the 9th floor of our apartment in Santiago
In a restaurant in Rio de Janeiro, trying to work during a Brazilian team’s game in World Cup 2018

If all you need to do your job is an Internet access, electrical outlet and headphones, than it’s not that hard to make yourself comfortable in whatever place you find yourself. But although WiFi is available everywhere, its level of reliability varies widely. Probably the worst place in terms of reliable Internet connection I’ve yet encountered is Galapagos islands. In Puerto Ayora, the main town on Santa Cruz island where we stayed a few days after completing our cruise, waiting for a flight back to the mainland, the connection was dismal. Wandering from one cafe to the next, I was searching for a signal, like a shipwrecked sailor gazing at the sea, hoping to sea a sail on the horizon.

Galapagos islands are not to be missed. Just don’t bring any work here.

You would have thought the universal adapters have by now solved the issue of outlet differences between countries. And yet, there are always surprises. I spent the morning hours of my first work day in Buenos Aires hunting for an adapter. The sad face of Argentinian plugs was just too much to handle for my universal adapter.

Buenos Aires, the capital of the saddest power plugs on the continent

Despite what some people on Instagram may let you believe, digital nomads don’t pass all of their work days on tropical beaches or exotic locations. At least most of my work time has passed in regular cafes or in our apartment, if it had the luxury of a separate room with a desktop. When the WiFi in our Medellin apartment died one day, the closest hotspot turned out to be in a small cafe, inside a jumbo supermarket.

Forget beaches – for a truly unforgettable experience, pass a day working next to endless shelves of wash detergents

Can Anyone Do This?

If you’ve read this far, you might be attracted by the idea of taking your own family on a long-term trip, all the while maintaining employment. And you might be asking yourself if it’s doable. The answer of course depends on your specific situation. But I would argue, it’s easier than it might appear.

Tijuca forest, right in the middle of Rio de Janerio. The last large city on our route, Rio turned out to be one of our favorite places on the continent

I’m lucky – I can do my work online. But until fairly recently, I didn’t realize I had this option. I never worked remotely until I decided to try to find a remote job. Could it be that there are hidden opportunities in your own life?

Another thing to consider is how mobile is your family. There is a huge difference between moving around with one preschooler or with 3 toddlers.

But if your skills can be potentially applied online to keep an income coming, and your family is fairly mobile, than the answer is yes. All the other concerns you might have – regarding safety, health insurance and such, are either things that are settled through online research, or FEAR. Fear is normal. I would lie if I told you I haven’t felt fear that first night in Guadalajara.

Baby steps. How do you begin a two-year trip around the continent? By telling yourself you are just going for a month.

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10 Replies

  • Mike, Thank You for the articles. I always enjoy reading them. I am fortunate enough to be retired and living in San Juan del Sur, Nicaragua. Keep it up please!

  • I loved this article too…as I told you before, you are a good writer! I love your trio’s spirit, and think you could not have done better for your son (as well as yourselves!) I grew up in a family where my father was in the diplomatic corps, and I would not change that exposure to the world as a youngster for anything!

    We have based ourselves in Quito, but we travel around the world about 5-6 months a year. Like you, we like to stay in Airbnb’s, at least a month in each location. I too bring my vegetable peeler and a chef’s knife to make life in the kitchen good 🙂 Next week we are heading to Antarctica for two weeks (on a ship…) Keeps us young, lol!

    Keep going! You, Oxanna and Ayan are an inspiration!

    • Thank you Dafna for your kind words!
      What countries have you visited as a child? How long was each mission? Was it easy for you to move from place to place? You didn’t you feel “out of place”, torn from friends? Would love to hear more details about your childhood experience, since these questions occupy us a lot, as we think about Ayan’s childhood and our own plans for the future.

      Enjoy Antarctica, would love to see the photos you bring back!

  • Thanks for the follow up to your posts which I enjoy immensely. You will never regret this sojourn and neither will your wife & small son.

    • Thank you Curtis! Experiences such as this definitely stay much longer in our memories than any positive emotions that come from buying stuff.

  • My dear Mike,
    Your description was genial…I loved your text and i wanna share with you, Oxanna and Ayam that, in two or three months, i’ll start my “big travel around the world”!!!But, i”ll follow your advice: “baby steps; i’m just going for a month”…Hope find all of you again, soon, in Canadá, Russia or Israel! Love from Brazil

    • Iabi, thank you my dear!
      I’m so happy to hear you are about to begin your adventure! All you need is to know your first destination, and from there, let the path unfold before you.

      Looking forward to reading and seeing photos from the road, and of course, seeing you!

  • Great post, Mike.

    I can’t wait to hear your story about the cat.

    Guadalajara is a good place. At least was for my two days there first time last Nov.

    Your travels with family are very inspiring!

    I signed up withe the conversations site you mentioned.

    • Thank you Dan, glad you enjoyed the post.
      Yeah, the story about the cat is pretty funny, have to write it down.

      Enjoy ConversationExchange – we met there some of our best friends during our travels.

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