This as-told-to essay is based on a conversation with Bakari Akil, 37, a private equity investor from New York. Akil grew up with no international travel experience and, three years ago, set out to visit 30 different countries each month. He finished his list, but is still traveling around the world. The following has been edited for length and clarity.
People I knew were traveling around and out of the country, and doing all this really cool stuff, and I was just like, "How are people pulling this off?" I just couldn't figure out how people were living these cool lives.
While I was at the Equinox on 67th Street in New York City, one of my gym friends had just come back from a trip internationally.
I said, "Yo, how do you travel like that?" He said, "I've been doing this since I was a kid." I didn't have any international traveling under my belt at all.
He told me to look into this program called Remote Year. I looked it up. The program takes other digital nomads, people who don't have to be locked into whatever location, on month-long trips.
Remote Year would find your housing, they'd find stuff for you to do inside the country, and they'd introduce you to people who were there. They even covered the flights between the countries as you were going to the next country. The only thing they didn't cover was food.
It was all-inclusive in a monthly $2,000 fee. I was paying about $3,000 a month to live in New York City just for rent — not including the gym and all that other stuff.
They're saying I can go live in a different country every month for 60% of what I'm paying for rent? What am I doing, of course I should do this.
I learned about it in March 2023, and I was on the trip with them by July.
I had a strict list of 30 countries I wanted to visit
I got on a plane, and I flew to Cape Town, South Africa. I traveled with Remote Year for four months. We went to South Africa, Greece, Spain, and Turkey together.
Then in Turkey, I left them. Since then, I have basically lived in a different country every month.
I went to India, then Thailand, then Vietnam, all throughout Southeast Asia. Then I went to East Asia: China, Japan, and Korea. I went to Jamaica, and then I flew to Ghana, Nigeria, Kenya, Ethiopia, and Egypt.
Then I spent a month in Israel and Palestine, going back and forth between Tel Aviv and Ramallah.
I did a European tour last summer. I was in Berlin, and then I spent a month in London, Paris, and Rome.
After Rome, I went to South America for the first time. I went to Peru. And then I went up to Mexico. I spent a little bit of time in the Caribbean in Cuba, the Dominican Republic, and Puerto Rico. Then from Puerto Rico, I flew to Colombia, Brazil, and Argentina in March of this year — that's when I officially wrapped up my specific tour of 30 countries I'd wanted to go to.
A lot of people got a chance to study abroad — I didn't get a chance to do that. So this was me catching up.
I tried to keep my expenses consistent across countries
My travel expenses between the nations were a couple of hundred dollars. If I'm flying from America to Thailand, it's going to cost me maybe $1,000. But if I'm flying from Cambodia to Thailand, it might cost me $100.
The idea was: while I'm right next to places, go visit them and make it easier.
In Asia, Africa, South America, and parts of the Caribbean, it would be very difficult or very unlikely for me to spend more than $2,000 a month on housing. The platforms I would use primarily were Airbnb and Booking.com.
Airbnb has always been the best for me because I want to cook, and it's not impossible, but it's harder to find hotels outside Asia that will provide you with a room that also has a kitchen.
In each place, I'm staying for a month, and I'm spending about $2,000 to live, and not in a faraway area — in the same kind of building that I was aspiring to live in when I was living in New York.
When I was in South Africa, I was living in the Victoria and Alfred area, which is the most expensive area in all of Cape Town, and I paid less than $2,000 for the month.
But the cool thing is that, unlike rent, when I'm in London for a month, and I know I'm going to be spending 12 months abroad, one month might be $2,800, and the next might be $1,400. It ends up balancing itself out.
Right before I left on my trip in 2023, I also applied for dual citizenship (I'm Jamaican by lineage). I got my Jamaican and American passports, which made it easy for me to navigate throughout Africa because there are certain nations where, if you bring your Jamaican passport, you don't have to pay a visa fee, or you can pay a lower visa fee.
So with a Jamaican passport, Ghana is visa-free, and Nigeria is cheaper than a United States visa.
I wanted to travel the US, too, but it's so expensive
After I finished my initial trip in March, I came back to the US for a month. I spent a month in Washington, DC, and was excited to come back to the US.
In fact, I was thinking I was going to do the same thing I had done internationally. I'll spend a month in Washington, then a month in Boston, then Chicago, and New York, and get a good sense of my home country. I'd been international, and I hadn't done the same thing at home.
The first time I went grocery shopping in Washington, DC, I was like, "What is going on? Why is it so expensive?"
In the rest of the world, you go inside a grocery store, you spend $50, and you have a very well-stocked fridge.
I'm coming from Argentina. I go back to the capital of my country, and it's just like, wow. It's unaffordable — and I'm not poor. It felt like the quality of life outside the United States was better than inside the United States.
I'm looking for somewhere to stay longer
After coming back home, I feel like I'm an international guy now.
I'm in Bangkok now. But now I am thinking, "Where are those places I can stay permanently?" Mexico City's one of those, Bangkok is one of them, Nairobi, Cape Town, and a few others.
I am a very big proponent of ownership, but I've always felt like the idea of owning your own home for the purpose of owning a home felt like a vanity thing — not necessarily a great financial situation. People end up spending way more than what they intended to spend when they buy their homes.
And the flexibility to wake up and say, "All right, Bangkok was nice. Now let's go to X, Y, Z," is impossible if I own a home.
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Jordan reports on moving trends — from remote work to house hacking. He also writes about movers struggling with issues around relocating like buyer's remorse and the many intricacies of moving to an unfamiliar state. He also has stories focusing on property technology and in 2022, moderated a panel on fractional investing at real estate technology conference Blueprint. Before Insider, he covered luxury real estate in South Florida for The Real Deal. He holds a Master's degree in Magazine Writing from New York University and a Bachelor's degree in English from Florida State University.













