When Travel Leads to a Forever Home

Image: View of Portland, Oregon overlooking the Willamette River during fall. (photo via jose1983/iStock/Getty Images Plus)
Image: View of Portland, Oregon overlooking the Willamette River during fall. (photo via jose1983/iStock/Getty Images Plus)

Have you ever had the experience of never wanting to leave a travel destination? Are you drawn back time after time to the same vacation getaway? Perhaps it's time to consider making a permanent move to your happy place. 

It happened to us, and it took a leap of terror to achieve our dream. Many might think we were too old to take on such an adventure, but it’s never too late to stop sitting around thinking “what if” and just do it. Obstacles may seem overwhelming, but if you map it all out, make list after list and check off all your boxes, you might just find yourself living your dream.

Our story started with a trip to Portland, Oregon, several years back to visit an old friend. Traveling cross country, on the diagonal from Florida, we were heading to a wedding in Big Sur and decided to check out the northwest, taking our friend up on his invite. We were immediately smitten with the natural beauty of the Rose City, and the temperate summer weather was a relief from the heat of the southeast.

A year later, when our son expressed an interest in moving to Portland, we were all for it. With suggestions for lodging and places to visit during his exploratory weekend, he set out to, ultimately, find his new home. He felt the same easy, friendly vibe we had experienced during our first visit. As soon as he returned, he put his house on the market and never looked back.

Over the next five years, we made many visits to our son's new home state and explored more of the city and its surroundings. The cool, crisp air and frequent sightings of Mount Hood and St. Helens never get old. The mass transit system is phenomenal, with many options available on whichever side of the Willamette River you land.

If I sound like a fan, you are most definitely correct. Each time we visited, we didn’t want to leave; we felt this place was where we belonged. Back home, we had family and friends, including seven grandchildren. We knew we would miss them terribly, but Portland kept calling us back. The thought of selling everything we owned and heading to a new state with only a few boxes and suitcases was daunting. 

We left what often felt like the tourist capital of the world, Orlando, Florida. Having lived there since childhood, before Disney, the theme park sector of the city had lost its sparkle and turned into an area that many locals avoid. Some may want to separate their vacation favorites from their permanent residence for this very reason. That old saying, "be careful what you wish for," might apply to some destinations more than others.

We visited Portland during each season, including the occasional snow event, as well as the anomaly of 100-degree summer days. We stayed in basement studios as well as upscale downtown hotels. We walked the city and the surrounding neighborhoods, searched for waterfalls and drove to Timberline Lodge atop Mount Hood. 

An aerial view of Mount Hood with Timblerline Lodge at the bottom

An aerial view of Mount Hood with Timblerline Lodge at the bottom. (Photo Credit: Jesse Cobb Photography / iStock / Getty Images Plus)

Our curiosity has not wavered, and we expect to be exploring for years to come. Having previously lived in a flat, sunny state, the daily walks in the northwest are full of surprises, and we sometimes feel like we’re on a different planet. But we never feel like aliens in this new region, as we’ve been warmly welcomed at every turn. The final test will be getting through a dismal, rainy winter. However, we feel it will be worth the chilly temperatures when spring arrives and explodes in the Rose City’s namesake flower display.

If we need an escape from the cold, we have the Mexican Riviera to the south and Hawaii to the west, providing many options and new destinations to explore.

So, if you are toying with the idea of becoming a resident, rather than a tourist, in your favorite part of the world, do your homework, try to remain realistic about the outcome and go for it. Life is short; just do it.


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CEO of Zenbiz Travel, LLC

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Helping leisure selling travel agents successfully manage their at-home business.

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Laurence Pinckney

CEO of Zenbiz Travel, LLC

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