Remote Work Travel Diaries: Canada

Alejandro Gómez
March 26, 2018 ·

For me, traveling to Canada was a lifelong goal.

At school, I remember attending a talk about studying abroad there. But I’d have to cover my flight, my school fees, food, and transportation—and my family didn’t have the money. We could barely afford my college studies in Mexico. So for a long time, the trip became a beautiful dream.

But as time passed, and my career developed, and I became more independent—Canada stayed on my mind.

I knew, if I went, I didn’t want to just visit for a few weeks, and come back home. I wanted to work there, take transit, walk the streets after work, meet friends for a beer. I wanted to live there.

I started working at Convert in 2015. Since then, the company has helped me to grow economically, professionally and personally. Here, we embrace a culture where we’re open about our personal goals, challenges, and plans. We all understand that our work is intimately connected to our personal lives and that we’re more than “human resources”—we’re people living in this world trying to be happy while we provide value to our customers.

While working at Convert, I’ve learned, that life goals can be achieved not only by working hard, but by working strategically. Organization and time management is the key to getting things done.

Work + Travel: Logistics

At Convert, we have monthly meetings called 1-1’s. They happen between a team member and a mentor.

It serves as a safe space to have conversations about personal and professional goals, challenges and frustrations. It’s purpose is to help the people to move forward, to recognize and address their problems, to work on their challenges, and, one of the things I love the most: to celebrate their achievements.

(At Convert we structure them similar to the smart people at Asana).

Having these 1-1’s helped me to organize the list of what I needed to do in order to make my dream come true. Not only did I talk about my work projects but I was encouraged to put my trip goals on the table. Understanding my trip goals allowed me to ask and find the answers to my questions. Here is an example:

  • What’s the best season to visit?
  • What are the cities that I can visit and continue working during the week?
  • What immigration papers do I need?
  • How much will it cost to live?
  • Do I need US Visa if I have a US stop-over flight?
  • How do I find good coworking spaces?
  • Do I need medical insurance?

These questions laid the foundation for my trip. My spreadsheet grew large but every step I took moved me closer to Canada.

Finally, after wrapping up my foundation questions: this is the itinerary that I created for my “Canada Experience”:

Cities to visit: 5

  • Vancouver: 1 week
  • Toronto: 2 weeks
  • Ottawa: 1 week
  • Montreal: 3 weeks
  • New York: 1 week

Travel within Canada: Train
Accommodation Type: AirBnB rooms
Travel Documents needed: US Visa for layover flight, and for visiting New York, eTA application for visiting Canada, Mexican Passport.
Health Insurance: Mexican private health insurance with international coverage for 2 months.
When to Travel: I wanted to travel in Spring of 2017, but due to the Visa application timeline, my trip was delayed to Summer 2017, Starting July 3rd.
Coworking Spaces: All these cities had plenty of Coworking spaces available in the center area, plus I knew I was able to work from any Starbucks (my weakness!) with a decent internet bandwidth.
Cost of travel: I calculated flights, train tickets, cheap AirBnB rentals, and set a daily budget of $100 CAD for food and travel. It was around $5K USD for the entire trip.

Week 1: Vancouver

During the process of planning this trip, I came across this train route called “The Canadian” which goes from Vancouver to Toronto crossing the western and central Canadian provinces in 4 days. I wanted to experience this, so I decided to include one week in Vancouver even though it wasn’t in the initial plan. So I arrived in Vancouver on July 3rd, 2017, finally realizing my dream.

Vancouver is very easy to fall in love with. The great pines all around the city, the majestic green parks, the Harbour and its Waterfront station, the Financial District, Chinatown, and Gastown. I was amazed with all the places this city has to offer. No surprise why this is one of the most desired cities to live in (and of course one of the most expensive).

I had to figure out 3 things: What bus to take to downtown, how to pay for it, and locate a Coworking space. The coworking space I chose was Creative Coworkers, located very close to Gastown and the Harbour, so I had delightful walks after lunch the week I was working there.

This first week was the most important week for me, since I was also breaking my cultural barriers and adapting to the rules in Canada and learning the differences from my hometown. So, after learning the Canadian “how-to’s” in Vancouver the subsequent cities were pretty easy to integrate with. Some of the most notable:

  • Tap water is potable and free to ask in every place you go. In México we have to buy bottled water.
  • Every city I visited has separated trash cans on the streets, where you have to mind whether your trash is plastic, paper, organic or landfill.
  • The pedestrian generally has the right of way when they cross a street.
  • A street must be crossed on the corner and following the pedestrian light.
  • You can get a fine for jaywalking. In México we only have lights for pedestrians in big cities, and within such cities, only available in the crowded areas!
  • In Canada, daylight duration lasts 15 hours during the summer, and 9 during the winter. This is, of course, because it’s a Northern city, while in Merida, Mexico, which is closer to the Equator, day and night lasts almost the same all year long.
  • When you enter to a Canadian house, is very likely that you will have to remove your shoes at the entrance, and wear slippers or walk barefoot. My friends told me this is because in the winter your shoes get wet and muddy.
  • Canada and US are credit card friendly. Everywhere you go you can ask for the payment terminal where you insert your card, and you process the payment. Your card will never leave your sight. In México people usually don’t trust this method because in order to pay, you have to give your card to the clerk and then sign a voucher. People are afraid that their credit card data will be stolen (and it commonly is).

I spent all my working days of this week wandering around Gastown and the Financial District, and for the weekend I decided to take a tour to Victoria, the capital of British Columbia, which I absolutely fell in love with. I’d say 1 week wasn’t enough to discover all the places Vancouver has to offer. I have to go back!

Gastown, Vancouver B.C.
Gastown, Vancouver B.C.
The Financial District, Vancouver B.C.
The Financial District, Vancouver B.C.
The Ferry that crosses to Vancouver Island, where Victoria is located.
The Ferry that crosses to Vancouver Island, where Victoria is located.
The Butchart Gardens, a must visit when you go to Victoria!
The Butchart Gardens, a must visit when you go to Victoria!

Week 2: The Canadian Train

The Canadian is the name for the world famous train route that crosses Canada, connecting the cities of Vancouver and Toronto taking 4 days. It crosses five provinces and four different types of landscapes. You get a really broad picture of Canadian scenery by taking this train. It’s breathtaking! The travel experience starts with the huge coniferous forests of British Columbia, through the Rocky Mountains in Kamloops and Jasper, where if you take this train in Winter, the scene becomes snowy white. After leaving British Columbia, you enter the golden prairies of Alberta and Saskatchewan, and part of Manitoba, to finally enter Ontario where the vistas of lakes so huge they look like oceans continue for hours. Then you reach your final destination: Toronto.

Working on the train would be tricky. Unless you have a stellar wireless mobile plan, you won’t have continuous internet along the route. It only seems to exist in the main cities. But really, there is so much to see you don’t want to be working!

View of the train cars from the Skyline train.
View of the train cars from the Skyline train.
A lake view from my window, leaving the Rocky Mountains in B.C.
A lake view from my window, leaving the Rocky Mountains in B.C.
The lush prairies from the dining car.
The lush prairies from the dining car.
At Capreol Station near Sudbury Ontario, one of the many stops on the way to Toronto.
At Capreol Station near Sudbury Ontario, one of the many stops on the way to Toronto.
A 30 car long train, a maker of memories.
A 30 car long train, a maker of memories.

Week 3-4: Toronto

Living in Toronto was easy for two reasons. Firstly, I already was adapted to the general Canadian cultural differences, and secondly, Toronto has everything for the professional who lives and works in technology. There are an abundance of coworking spaces with excellent bandwidth, an outstanding transportation system, lots of AirBnB rooms, delicious international food (as well as almost everywhere in Canada), and tons of entertainment options.

I decided to work at the Workhaus, a set of coworking spaces located in the Financial District. They’re very close each other, so I was able to work in different places by paying only one membership. Since I stood in this place for two weeks, they gave me a special price for this period of time, $150 CAD (~$115 USD) for the whole period.

I also decided to stay in two different AirBnb places for the two weeks I was in there. The reason for this is that I wanted to experience living in different neighborhoods including the commute from each one!

I decided to buy the City Pass—and to get the most of it during the weekends. The CN Tower, the Casa Loma, the Royal Ontario Museum, the Ripley’s Aquarium of Canada, and the Toronto Zoo were the ones I visited.

If you’re going to work remotely, and explore Toronto, you’ll probably need more than two weeks. Plus, you shouldn’t miss not miss the Niagara Falls, which are at the border between Canada and the US.

A view of the Rogers Centre.
A view of the Rogers Centre.
A view of the City and Lake Ontario from the CN Tower lookout.
A view of the City and Lake Ontario from the CN Tower lookout.
A music festival at Yonge-Dundas Square.
A music festival at Yonge-Dundas Square.
The Casa Loma
The Casa Loma
How beautiful bedrooms used to be, this is a one inside the Casa Loma.
How beautiful bedrooms used to be, this is a one inside the Casa Loma.

Week 5: Ottawa

I left Toronto via train to Ottawa, taking a 4 hours trip—in business class, baby!

Pro Tip: If you buy your train tickets in advance online, you can get the Business class cheaper than the economy plus!

I arrived to Ottawa at 13:00 hours, took a taxi and went to my Airbnb, where I met Francois, my host for that week. The place was well located, just 10 blocks away from the very center, where the Parliament and other historic buildings are located.

My words do no justice to Ottawa’s beauty.

It is worth to mention that you won’t get bored in Ottawa. You can enjoy walking around the Parliament buildings, admire the Ottawa River scene, walk all along Wellington St, visit the War memorial, the Rideau Canal, going to the National Gallery of Canada, the History Museum of Canada, located in Gatineau, shopping at the Rideau Centre. There are so many interesting places in a 5km radius.

It’s also a very easy place to work. Only 10 blocks from my AirBnb, I had 2 Coworking spaces, 5 Starbucks, 10 Tim hortons, plus many interesting restaurants to eat in. Every day I had the right balance of delicious food and good exercise. I got the luxury of eat everything and burn it right away by walking a lot exploring the city.

The two places I chose to work at, were, the Biz Lounge, in Connor St, and the Impact Hub, in Slater St. both places very close to the Parliament and the city center.

Week 6-8: Montreal

Montreal was the city I stayed the longest in.

Everyone told me “You’re gonna love Montreal”—even the people that I met during my trip, told me that I was going to love Montreal. They were not lying. Plus, my friend Morgan, from Convert, lives there, how is it possible to not visit this city?

While Vancouver, Toronto, and Ottawa are cities with British heritage, Montreal represents the French side of Canada. Once that you enter to Quebec, you feel you’re in a different place, different culture.

One thing you notice by just walking in the urbanized part of Montreal, is that Quebecois know how to decorate. Every restaurant, every museum, bookstore, office building, is more than just a building. Even the Metro stations are beautiful. They’re more than just buildings with squared angles.

Another thing about Montreal that will prevent your walks to be boring, is that you will find murals everywhere. People like to decorate buildings walls in there. The city is a painting museum.
And the churches, there are churches everywhere. Really.

Here in Montreal I decided to stay in two different places as well as in Toronto. My first Neighbourhood was Saint Henri, a former worker class neighbourhood that has been gentrified recently. This used to be one of the most dangerous Neighbourhoods in Canada, but thanks to this new fresh wave coming, it has become one of the most attractive to live in. I had many restaurants, coffee shops, one nice coworking place (Le Tableau Blanc), laundry, and a convenience store in a radio of 20 blocks.

The last two weeks, I moved to Cote-des-Neiges, some Metro stations away from Saint-Henri. This neighbourhood is more recent than Saint-Henri in a way that you’ll find 4-6 stories building instead of Fancy Duplex apartments, this neighbourhood is populated mostly by immigrants,

which means there’s more chance to find people from around the world here, and therefore, restaurants from around the world. I tried Vietnamese, Lebanese, Chinese, British, even Mexican food in here.

So, besides the Le Tableau Blanc coworking space I rented in Saint-Henri, I liked another beautiful Coworking in Old Montreal: Crew Collective, a historical building that used to be a 1920s bank, and now welcomes digital nomads, travelers, creative people. You must visit this place!

Apart of this, there is the place you cannot miss when you’re visiting this city: The Mont Royal. This place is a symbol of the city, is a hill or small mountain in the heart of the city, with a beautiful Chalet at the top of it, where you can take beautiful pictures of the city from the lookout. In this place you can go to have a picnic with friends, go hiking, running, ciclying, enjoy music festival during the year. This is nature inside the city.

Week 9: New York

For my last five days of the trip, I chose New York, the famous capital of the world.

I won’t describe New York, I just cannot. It has so many things that you’ll need thousands of words for it. Here’s what I liked about it.

So, you walk from your airbnb to the next Train Station, go downstairs, pass your card, enter to the halls. There is a high chance you’ll find a band playing jazz, funk, fusion. Then you get into the train. There’s a high chance you’ll find a band or any artistic spectacle in the car. You arrive your destination, get out of the train, go upstairs, walk among hundreds of people in the sidewalk, alongside lots of yellow cars in the streets, huge buildings rising to the sky. The vibe is dynamic, no one is quiet, the noise is enchanting—horns, voices, music, light reflecting on the crystal windows, and scaffolds that you must walk through. A bag of trash, another one, plenty of that here, you walk more blocks, everything is clean, there’s a park ahead of you. The sun is setting, the lights are taking over. You’re heading to Times Square to meet a friend. Suddenly you’re surrounded by lot of people and a festival of lights. The big screens are always changing, everyone is taking selfies, Mickey Mouse is playing with Spiderman and the next Flash Mob is about to happen.

The next day you have breakfast in the Upper West Side, just few blocks from Central Park, then you go to spend the rest of the day in the park, you get lost, you find a lake, another lake, this one has ducks, you take pictures of them, you start chatting with a lady that goes there to enjoy the view and paint a picture of the lake. You wonder how come you can breath fresh air and find peace in a lake within a park within a concrete noisy jungle, in an Island. You look at people, some are laying on the grass, some are walking, running, cycling, playing with their kids.

New York is Beautiful.

The last day, I took a taxi and headed to the JFK Airport, checked in for my flight, arrived to Mexico City, then took another flight to Merida; arrived at the late night after spending all day traveling, and gave a big hug to my mom and my sister which went to the airport to welcome me.

I was nostalgically happy. My two months adventure had ended.

So, how was this possible?

This is what I think was the things that helped me to make this happen:

  • The first thing that allowed me to travel two months without being rich, is remote working. Having the freedom to work from anywhere as long as I have a laptop connected to internet was decisive to do this.
  • The second one, is having a job that allows me not only to earn good money, but pushes me to be a better person, to grow personally, to pursuit and achieve life goals.
  • Saving. I had to be frugal for about 6 months in order to save money for flight and train tickets, AirBnB reservations, food, and leisure expenses. Don’t forget that 1 Canadian dollar was equal to 15 Mexican Pesos in 2017. A meal in Canada was twice the price than in Mexico.
  • Convert covered most of my Coworking spaces outside. We have a decent budget that can afford an average coworking monthly membership in a developed-world city. I mean, our budget is really good.
  • The places I visited had great internet coverage, as well as good bandwidth for the average place: over 20mbps.
  • Planning: My 1:1 meetings helped me a lot to organize my schedules, the cities I wanted to visit. I received a lot of guidance from the Convert HR Champion, Morgan.
  • Internet. For every doubt you have in these days, Google is your friend, really, you don’t know what to pack for 2 months? How to pack them? Google it. You don’t know whether you need a visa to enter a country? Google it!.
  • Be fluent in English: My native language is Spanish, and because of my career, English is my second language. I wasn’t able to speak it fluently until I entered into a company with an international team, where you’re forced to understand and speak English to communicate each other. Speaking English really makes a difference when you travel around the world.

What I’ve learned

Despite I enjoyed this travel so much, there are some things that I discovered on the road, and I’ll do differently on my next adventure:

  • Stay more than 2 weeks in a city. It is important to notice that staying less than 2 weeks will affect your productivity. This is why:
    • Your first 2 days are your more important days, you have to move to your new home, then you have to know how to move, buy a transport card, get to know the bus/train routes. If you have to walk through the streets, or underground malls, like me in Toronto, you might get lost. I actually missed a meeting because of this, I got lost in Toronto underground halls. So it’s something to have in mind if you’re working and traveling.
    • 1 weekend is not enough to discover a medium or big city. If you’re traveling and working like me, you’ll wish to have at least 2 weekends (4 days) to explore the center, the outer sides, the attractions. I did this because my money only allowed me to be in Canada 2 months and I wanted to know as much as I could.
    • After 3 weeks, you’re a local. Your brain already knows where’s the laundry, what station to get on and what to get off from the subway. By that time you’d already meet some people at coworking, and there’s a chance they’ve invited you to attend a social event, maximizing your chances to know more people. Because this is what it’s about for some people: to have friends around the world, right?
  • Value the cities where you have friends. It is true that being alone in a new city is exciting. Everything is new, and you’re on your own. But having a friend in a new city is golden. They know what places to visit, they know what places to avoid, they know what events and festivals are happening during your stay, and most importantly: they are your friends, they are joining you on your experience, shaping beautiful memories for the future. Value that!
  • Learn in advance about the transportation and the coworking spots before you get to the place. You can use Google to search for coworking places in your new city. I use to find the best place that will be closest to my AirBnB room. Use Google maps to find routes if there is any in the city. Google maps has updated info in the world main cities. Check if there’s Uber in the city, or a similar app. It’s safer and cheaper than the average Taxi.
  • Bring a camera with you. A video camera, a DSLR, any is valid. Bring a power bank for your mobile and for your camera. I bought a GoPro session to record my adventures. I also bought an external Hard Drive because I took tons of pics and videos. These will be your memories in the future.
  • Buy a nice backpack. Invest in. for safety, for the sake of your back. It will be your valuables holder. It’s worth the price.
  • Try to travel light in your backpack. Your back will say thanks. Especially when you’re waiting in the airport, or when you’re walking to the Coworking.
  • Keep your passport close at hand and in a safe place.
  • Bring an extra Credit Card if you can. Put it in a different place than your wallet.
  • In Canada and the US, try to pay with Credit Card. Most of the stores and businesses places are CC friendly, plus it is better to check your numbers from your bank balance sheet. Still carry some cash for unexpected events.
  • Save your Google codes, in case you lose your cell phone.
Originally published March 26, 2018 - Updated December 15, 2021
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Alejandro Gómez
Alejandro Gómez I help to build and maintain the web application at My aim is to deliver a good user experience in collaboration with our great UX Design team.

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