Olá Portugal: Why I Moved to the Land of Sunshine and Sardines (and how you can too)
By Dennis Bailey
An old friend was teasing me recently about my lack of travel experience. I have never left North America, and as an adult, haven’t ventured past New England, the Canadian Maritimes, and Quebec very often.
I’m OK with that, because I think the region has enough beautiful, and culturally rich corners to keep me busy for the rest of my life.
But my wife hopes, in retirement, to visit Italy for its culinary delights. I’m more partial to Ireland. But now, after reading Dennis Bailey’s interesting little book, Olá Portugal: Why I Moved to the Land of Sunshine and Sardines (and how you can too), I think I may have a compromise.
Bailey is an interesting character. He grew up in Livermore Falls, a paper mill town, and ended up in journalism, including a stint at the Lewiston Sun-Journal, and then landed a gig as Gov. Angus King’s communications director.
Bailey dives into the details on everything, from how to order a cup of coffee to banking…
Later, he formed a PR firm, Savvy, Inc., working for political candidates and businesses.
About eight years ago, he faced a fundamental question:
“One morning, around 2016, I woke up in bed and thought, ‘Why do I live here?’ I had recently been divorced (for the second time), both my parents had passed … my daughter was living far across the country in San Francisco, and my two brothers were in different states…”
And yes, for the liberal-leaning Bailey, the political climate was a factor:
“The intense polarization, the politicization of everything, was tearing the country apart, wearing me down. I kept hearing Rufus Wainwright’s song ‘Going to a Town,’ in which he sings, ‘I’m so tired of America.’ After working for years in Washington D.C. politics, and decades before that in Maine, yes, I was tired of America — exhausted.”
When the book was written in late 2024, more than 14,000 Americans had landed in Portugal, a 44% increase from two years earlier, he writes.
For Bailey, COVID was a factor, as the early wave put him in the hospital for an extended stay.
“Ever since I got out of the hospital, I had this sense that I was just treading water, not fully living the time I had left,” writes. “And it dawned on me that I was already working remotely. My PR clients were all over the world; the best (and best paying) was in Western Africa. What did they care where I lived?”
Bailey takes pains to note that the book is not a travel guide. OK, and I’m not moving to Portugal, but it just rose to the top of the list of European countries I’d like to visit, thanks to the vivid, practical, and realistic depiction of the country he provides.
After a visit to scope out where he might live—on the coast, of course, but somewhere between urban and rural—he engages a guide to help him find a place to rent, and it turns out she is an attractive woman, and the two grow close. His friends warn him he is being “catfished,” but they meet on a subsequent visit, and are now a couple.
Rent is a lot cheaper than Portland, and even cheaper than Rockland. Public transportation can eliminate the need for a car. Crime and drug abuse are low. Most everyone speaks English well.
Bailey dives into the details on everything, from how to order a cup of coffee to banking, from how to buy food at a street market to why the roofs are all red.
There’s no sugar coating, though. He notes that cigarette smoking is prevalent, and people in restaurants treat their phones like walkie-talkies, holding them so patrons can hear both sides of conversation.
The history and culture run deep. Lisbon predates the establishment of Rome by 400 years. Coastal fortifications date to Columbus’ era.
My wife is a foodie, and I lean more toward pub fare, but even I was salivating at what can be enjoyed at a restaurant. And maybe the best part—the bill for fine dining is easily a third cheaper than a dinner in Portland.
As I said, Bailey is an interesting character, and his guide to the land of sunshine and sardines is fully entertaining and enticing. Even to a timid traveler like me.
The book can be purchased here.
Tom Groening is editor of The Working Waterfront.
