Searching for a Winter Home - Don & Marylou
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We didn’t want another vacation—we wanted to live somewhere and see what it felt like. From Chiang Mai to Cartagena, each place taught us something about what mattered—and what didn’t. Slowly, through trial and elimination, we found our way to a winter home we hadn’t expected.
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Trying the World Before Choosing a Home
In 2017, we made a decision.
We wanted to find a place to retire—but not by taking vacations.
We wanted to live somewhere for a month and see what it actually felt like.
So we began what we came to call our “international assignments.”
Our first stop was Thailand.
We started with a vacation, but when we got to Chiang Mai, something shifted. We loved it. So we did something that became a pattern—we started looking for a place to live.
Marylou found a rental. We called, and the owner said, “My wife will come pick you up.”
We went to see it and immediately thought, Wow.
He told us he had an opening in February. As we left, I said,
“Let’s go sit down and make a list of why we shouldn’t do this.”
It’s easy to get excited and list all the reasons to say yes.
It’s harder—and more useful—to look for reasons to say no.
We could only come up with one.
We already had plans to go to San Miguel de Allende.
That was it.
So we did it.
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We spent a month living in Chiang Mai—and we loved it.
The first morning, we went to play pickleball. We had found a group online, got lost trying to find it, but eventually showed up halfway through. The people were wonderful—Europeans, Americans, and Thai players. We ended up going to lunch with them that same day.
It was the perfect way to arrive somewhere new.
We lived in the Old City—surrounded by a thousand-year-old wall and a moat. I’ve always loved places like that, and Chiang Mai had a special charm.
We settled into a rhythm. I worked part-time on my website, just like I would at home. We went out to eat, explored, and lived—not as tourists, but as temporary residents.
But then we noticed something.
In March, the air started getting smoky. Locals told us it happens every year—farmers burn crops, and the air quality drops significantly. We also realized how hard the time difference was. Being 12–15 hours off from the U.S. made it difficult to stay connected.
So even though we loved Chiang Mai, we crossed it off our list.
Next came San Miguel de Allende.
Marylou knew it well. Her parents had owned a place there, and she had spent years managing it as a rental. I had been once before and loved it too.
It’s a beautiful colonial city, full of charm.
But there was one issue.
It sits at about 5,000 feet.
In the winter, it’s cool—cooler than we wanted. We were looking for warmth.
So we crossed that off too.
Then we tried Antigua, Guatemala.
It was a beautiful place—with a stunning house and a view of a volcano that changed every morning depending on the clouds. The people were kind, and the setting was dramatic.
But again—it was in the mountains.
Cool.
Not what we were looking for.
Then came Cartagena, Colombia.
We almost didn’t go. Colombia still carried a reputation tied to its past. But friends we met in Chiang Mai told us, “Cartagena is amazing—and very safe.”
They were right.
Cartagena was, for me, one of the most beautiful places we visited.
A walled city, full of history. Colorful buildings, flowers cascading down balconies, small plazas everywhere. It was incredibly clean—people were constantly sweeping the streets. One night, I noticed leaves on the ground and thought, That’s unusual. Within minutes, someone came by and cleaned them up.
The food was outstanding. High-end restaurants everywhere. It felt like an international destination.
We loved it.
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2019 became a year of travel.
We got married.
2019 became a year of travel.
We took multiple trips, including a wonderful time in Europe that ended in Venice.
But we still hadn’t found our place.
So we tried Mexico.
At the beginning of 2020, we went to Puerto Vallarta for a week—not as an assignment, just a visit.
We spent part of the time at a beach north of town that we didn’t like at all. But when we came back into Puerto Vallarta, something clicked.
We found a house we loved—but it was already rented for the season.
Then, on our way back through the San Francisco airport, we saw the first signs of what would become COVID.
Everything was about to change.
COVID Started
Later that year, before the pandemic fully took hold, we decided to try Puerto Vallarta again—this time for a full month.
We stayed at a small bed-and-breakfast run by Tom and Chuck, who would later become close friends.
Before arriving, I sent them a long list of all the safety precautions we were following. Tom told Chuck, “Don’t answer that.” Chuck—who thinks more like I do—answered every point.
We knew we would get along.
And then something familiar happened.
Marylou said, “Let’s look for a place.”
We started walking the neighborhoods—and we fell in love with one area: El Centro, especially a section known as Gringo Gulch.
We told our real estate agent,
“This is where we want to buy.”
She said,
“There’s nothing for sale here—and even if there were, you probably couldn’t afford it.”
Then she paused.
“Well… there is one building. Four units. I think one might still be available.”
That moment changed everything.
We bought the condo.
And Puerto Vallarta became our winter home.
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Test Life—Don’t Just Vacation It
Living somewhere for a month reveals what a short visit never will.
Look for Reasons Not to Do Something
Excitement comes easily—clarity comes from questioning it.
Lifestyle Matters More Than Beauty
A place can be amazing—but still not fit your daily life.
Small Frictions Become Big Over Time
Air quality, climate, and time zones may seem minor—but they shape the experience.
Let Each Experience Refine the Next
Every place we tried helped narrow in on what we truly wanted.
Discovery Is a Process, Not a Decision
We didn’t “choose” our place—we found it by exploring, eliminating, and learning.
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