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What it’s like to move to Mexico, Greece and Costa Rica


For many, 2020 will be remembered as a year they spent at home.

Some chose a completely different route. Others chose a different path. They moved to exotic places many people only dream about.

In their own words, here’s what they think about the decision after a year.

From Boston to Napa Valley, California

Name: Ian O’Reilly
Occupation: Sommelier

Before the pandemic, I was employed as a beverage manager in Boston. In March 2020, the restaurant I used to work closed and I was laid off. When I looked back at my life, it became clear that I didn’t want to be a restaurant manager. It was exhausting and stressful. In order to get involved in agriculture, I explored the idea of moving to Napa Valley (California) to try my hand at the wine industry.

My girlfriend —  who is also an advanced sommelier —  and I moved to the town of Napa in September of 2020 with our two dogs. I didn’t have a job and realized quickly that there was a very small job market due to the pandemic.

Ian O’Reilly came to Napa Valley in search of work. He now holds two positions within the wine business.

Courtesy of Ian O’Reilly

At that point, I was hired to host online wine tastings at Virtual With Us. This was the first time I had ever worked from home. I met several other sommeliers across the country, many of whom had just lost their job in restaurants. The team was high-quality and I was delighted to be part of it.

In April of last year, I was hired as the logistics manager for a wine startup in Sonoma. However, I continued hosting online events. My wine knowledge was reshaped when I merged the two. My inventory now includes rare and fine wines. I also have the opportunity to discuss them online as a virtual wine sommelier.

It’s less work and I have more fun. Napa has a half-the cost of Boston.

I don’t plan on leaving at the moment. My permanent residence is in vacationland.

From New York City to Greece

Name: Peter Despotopoulos         
Occupation: Marketing director

In New York, I was the vice president and managing partner of a custom millwork shop. Because I felt truly unhappy at the place I worked, I made the decision to leave. I felt exhausted and drained all my life. My job was not what I wanted.

Even worse, the price of living was not a reflection of the quality of my life. I was drowning in debt because everything I enjoyed doing was expensive —  Knicks games, fine dining, concerts. New York City became a very expensive and densely populated city, with few options for basic pleasures.

Living in Greece costs less than New York.

Peter Despotopoulos   

Marketing director, Moro

In New York, I rented a one-bedroom apartment on the top floor of a new luxury 60-unit building in the Long Island City/Astoria area. I now rent a two-bedroom apartment in a six-unit modern building in an affluent part of Athens called Voula — an area known as the “Athens Riviera.” My apartment has a swimming pool and is just a few minutes walk from the beach.

Living in Greece costs less than New York. My monthly fixed expenses were $4,500, which included $2,500 rent and $680 car leasing. My company did not pay my cell phone bill or health insurance. My Athens apartment is 1,300 Euros per month (£1,520). Fixed expenses has been cut by half. The worst part about Greece is the price of gas — it’s about double that of New York.

Peter Despotopoulos, sixth from the right in back said that he walks to the beach each morning before starting work in the afternoon.

Courtesy of Peter Despotopoulos

Work is less stressful than before. I work remotely as the marketing director for a U.S. home furnishings website called Moro. Due to the seven-hour time difference, my workday starts at 3 p.m. and usually ends around 10 p.m. Greece is a late culture — everyone eats and goes out late — so I don’t mind the hours. Athens’ fantastic dining and nightlife are what I love before and after work.

While I enjoy dining at nice restaurants, I now prefer to go to the stadium on weekends to see Panathinaikos soccer. Beautiful Mediterranean islands are within a short flight distance or by ferry.

Peter Despotopoulos claimed that he swapped New York Knicks’ game for Athens Apostolos Nikolis Stadium soccer matches.

Courtesy of Peter Despotopoulos

Almost a year later, I think I’ve made a good decision. This is the place to be if you want to make a lot of money in Greece. Due to my Greek heritage, I knew what to expect and was able speak the language.

It can be difficult to spend time away from family and friends on some days, but I don’t deny that it is hard. Changes such as these require patience and patience in order to be successful.

From south England to Costa Rica and Mexico

Name: Alister Gray
Occupation: Executive coach and founder of
Mindful Talent

In October 2020, my wife and I made a quick decision to leave the U.K. with our 5-year-old daughter Rumi and travel whilst the craziness of the world sorted itself out. We were in Twyford, a tiny town. We could easily commute to London from there, and it was convenient for our small business.

Alister Gray was able to start his executive coaching firm from Costa Rica, Mexico after a stint in Bali.

Courtesy of Alister Gray

I’d trialed running executive coaching sessions and workshops from Bali, Indonesia, for nine months in 2018, when our daughter was 18 months old. It gave us the confidence to be able work remotely from any location in the world as long as we had access to Wi-Fi.

The pandemic struck as we were preparing to apply for U.S. visas. We decided we wouldn’t let it stop our ambitions to leave the U.K. and instead viewed it as the perfect opportunity to travel to a country we had long admired — Costa Rica.

Our January flight from London to Costa Rica was a success. Nosara, a beautiful home with a view of the Pacific Ocean was our dream house. Every morning, we were greeted by a family howler monkeys at our doorstep.

It was a wonderful six-month experience in Costa Rica. However, it wasn’t the right school for our daughter. We moved to Quintana Roo in Mexico to a small place called Puerto Aventuras. We met our dear friends while we were visiting them in April. It was a beautiful way to live. We were welcomed by a beautiful community of friends — a mix of Mexicans, Argentinians, Dominicans, Americans and Canadians.

Costa Rica was relatively expensive. Since then, the cost of living has dropped around 40-50%. Our expenses in Mexico are similar to the U.K. For example, our three-bedroom 1,200-square-foot condo costs around the same as our two-bed semi-detached home in the U.K.

After leaving Costa Rica (here), Alister Gray said his family lives a more active lifestyle in Mexico, where they plan to stay because they “love it so much.”

Courtesy of Alister Gray

Our quality of life increased with weekly help from maids, cooks and nannies. The beach is just a few minutes away, as well as tennis courts and runs and biking tracks. There’s also a nearby golf course.

We have made the most important decision of our lives. We’ve given our daughter, and ourselves, a freedom that we would not have experienced if we’d remained in the U.K.

From Las Vegas to a nomadic lifestyle

Name: Bryan Conzone
Occupation: Owner of data analytics and marketing company

We were living in Las Vegas when the pandemic started. Although I worked remotely over the years, my wife Jenn was an RN. She was made to leave because the schools closed and no care was available for our five-year old son and daughter (then five months).

We had been considering moving to Texas for many years after our lease expired in June. The plan was to spend a month in Austin and Dallas. Landing lets furnished apartments be rented for up to 30 days. This is how we discovered Landing.

The concept we liked so much that it became an ongoing conversation about why Texas is the best place to visit. It’s a good idea to take the opportunity and explore all of America.

Bryan Conzone stated that the rent prices for his apartments range from $1,800 to $3,600 per month. This is higher than his Las Vegas townhouse, but lower than his Orange Country rent, California rent, where he had lived for eight years before moving to Vegas.

Courtesy of Bryan Conzone

After Dallas and Austin, we stayed in Las Vegas; Seattle; Salt Lake City; San Francisco; Orange County, California; Portland, Oregon; and Scottsdale, Arizona.

When we left Vegas, we put our stuff in storage. Our only necessities have been clothes, books, and educational material. Amazingly, we’ve not missed 95% of our stuff in over a year.

The next step is to visit Boston, New York City (New York), Boston, and Denver. We then plan to make our way to the East Coast, starting in Orlando.

One year ago I wouldn’t have believed we would be able to explore the United States so easily. This trip has truly changed our lives and shaped how we live for the future.

 Note from the Editor: These responses have been edited to be more concise and clear.