As I sit at a cafe here in Anjos in mid-June, looking back on our second extended stay in Lisbon, I can't help but smile at how much has changed since our first visit. What started as tourist curiosity has blossomed into something deeper—a genuine connection to this remarkable city and its people.
Mendo Cafe
Finding My Portuguese Voice
The transformation from tourist to local doesn't happen overnight, but I'm finally feeling it. This time around, I found myself confidently navigating street markets and grocery stores, my broken Portuguese flowing more freely than before. There's something magical about that moment when you stop translating in your head and just... speak. The vendors smile differently when they realize you're trying, really trying, to be part of their world rather than just passing through it.
A vendor at a street market in Graca, (Tuesdays and Saturdays)
My language lessons are paying off, and with our banking and utilities sorted, we're building the infrastructure of a real life here. It's the small victories—successfully ordering at a local restaurant where no one speaks English, or negotiating for fish at the market—that make you realize you're becoming something more than a visitor.
Beyond the Tourist Map
This stay, I made it my mission to explore beyond the well-trodden tourist paths, and what I discovered was extraordinary. Just two metro stops from our home, I found a gym in Anjos and stumbled upon two neighborhoods that have completely captured my heart: Anjos and Arroios.
These areas are Lisbon's best-kept secrets—local markets, unique cafes, thrift stores, and art galleries create a vibrant tapestry of authentic Portuguese life. It's a melting pot where locals from all walks of life intersect, and tourists are refreshingly few. Here, you'll find everything you need and encounter the real heartbeat of the city.
The public transportation system, once intimidating, has become our lifeline. Clean, affordable, and rarely crowded (except for the infamous Tram 28), it's opened up the entire city to us. We've mastered the metro, and with it, unlocked a Lisbon that most visitors never see.
But perhaps my favorite "transportation" discovery has been Joao, our local cab driver who lives right in our alley. At 55, I've learned there's something profoundly different between hailing an Uber and building a relationship with someone who's called this neighborhood home for 40 years. Every ride becomes a Portuguese lesson and a history class rolled into one. Joao doesn't just drive us places—he shares stories of how our street looked decades ago, teaches us phrases that no app can provide, and connects us to the living memory of this ancient city.
A Culinary Adventure
Food has become our gateway to Portuguese culture. We've ventured into local restaurants where Portuguese is the only language spoken, and the warmth of the welcome has been overwhelming. For just 13 euros, you can feast on the national favorites: caldo verde soup (2 euros) and perfectly grilled fish with delicious potatoes (11 euros). These aren't tourist prices—this is how locals eat.
One of my proudest moments came at a local market, where our American friend Mel, a long-time Lisbon resident, introduced us to Portuguese vendors. Armed with broken Portuguese and Google Translate, I successfully bought my first dorado—six large pieces that I later cooked at home. The fish was delicious, but the experience of connecting with the vendors was even better.
The Economics of Expat Life
Living like a local has opened our eyes to the economic reality of Lisbon life. A typical grocery run at Pingo Doce costs us about 60 euros for a week's worth of food and wine. When I fed our receipt to an AI and compared prices to equivalent items in the US, the same groceries would have cost around 120 euros back home. The abundance of fresh fruit at every corner market and the accessibility of quality ingredients makes eating well both affordable and enjoyable.
Festival Season: When Lisbon Comes Alive
June in Lisbon is pure magic. It's festival season, and the city transforms into something extraordinary. The St. Anthony festival and sardines festival bring out the true spirit of Portuguese culture. Twenty-seven neighborhoods (bairros) participate in a month-long celebration of dance, music, and community that culminates in a spectacular parade.
We're fortunate to live at the intersection of three historic neighborhoods: Graça, Castelo, and Alfama. This puts us at the epicenter of the festivities, and while it can sometimes feel over-the-top, it's impossible not to get swept up in the energy.
These neighborhoods carry centuries of history in their cobblestones. Alfama, the oldest district in Lisbon, survived the devastating 1755 earthquake that leveled much of the city. Its maze of narrow streets and fado houses still echo with the soulful music that emerged from these very alleys. Castelo, crowned by the medieval São Jorge Castle, offers panoramic views that have watched over the Tagus River since the 11th century. Graça, perched on one of Lisbon's seven hills, has been home to churches and convents since the 13th century, creating a spiritual anchor for the community that endures today.
Alfama's traditional approach to the festival particularly captured my heart. Neighbors transform narrow cobblestone alleys into makeshift wooden patios, decorated with traditional colors and ornaments. They set up grills for fish and meat, Superbock beer flows freely, and everyone—young and old—comes together to dance to live music. As the night progresses, the energy shifts to DJ sets, and the young crowd keeps the party going until dawn.
The celebration peaks on June 12th with the grand parade downtown, where neighborhoods compete with elaborate costumes and choreographed dances. The following day brings the solemn St. Anthony procession, a spiritual journey from church to church that adds depth and meaning to the festivities.
More Than Just a Change of Address: A Midlife Renaissance
Living in Lisbon has fundamentally changed my relationship with daily life. At 55, after decades in corporate America, I'm discovering something I'd forgotten existed: the simple joy of being present. In Chicago, I often battled boredom, anxiety, and the crushing depression of long winters. The corporate grind had worn grooves in my soul that I didn't even realize were there until I stepped away from them.
Here, I can't remember a single day in the past two months when I felt that familiar weight. Sometimes, all it takes is opening the curtains and looking outside—the energy of the street, the mix of tourists from around the world, the constant hum of activity—it all feeds my soul in ways that conference calls and quarterly reports never could.
This realization has been both liberating and sobering. How many years did I spend believing that stress was just the price of success? How many moments of genuine happiness did I miss while chasing the next promotion, the next deal, the next milestone that was supposed to make everything worthwhile?
Travel, I've learned, isn't just about seeing new places—it's about seeing yourself in new contexts. For the first time in years, I feel optimistic about what comes next. Not because I have all the answers, but because I've remembered that life is supposed to be lived, not just endured.
This was our first Lisbon summer, and the locals definitely know how to celebrate it properly. We've experienced the city in August through December, which was wonderful, but June's traditional festivals took everything to another level.
The Human Tapestry
Any honest conversation about Lisbon must acknowledge its complex social fabric. This is a city of layers: locals who feel displaced by rapid touristification, immigrants from South Asia and Brazil working in the shadows while hoping for their piece of the European dream, tourists from every corner of the globe, and new expats from wealthier countries like us.
It's a renaissance city in the truest sense—things are happening here, constantly. There's a cultural richness and contentment that permeates daily life. The Portuguese have mastered something many of us are still learning: how to prioritize family and joy over money and accumulation.
Finding the Real Lisbon
The secret to falling in love with Lisbon is simple: step outside the tourist map. Just a few blocks away from the crowds, you'll discover the real city—one where neighbors know each other, where traditions run deep, and where life unfolds at a more human pace.
This cultured society has taught me about contentment in ways I never expected. There's wisdom in their approach to life, an understanding that happiness doesn't come from having more, but from appreciating what surrounds you every day. Manuel, our cab driver, embodies this philosophy perfectly. He's not building a transportation empire or optimizing for maximum efficiency—he's building relationships, one conversation at a time.
The Portuguese concept of "saudade"—that bittersweet longing for something that might never return—suddenly makes sense when you're 55 and looking back at decades of chasing things that ultimately didn't matter. But here's the beautiful irony: in a city steeped in saudade, I've found not longing, but presence. Not what was or might be, but what is.
When the tired tourists return to their Airbnbs in the evening, we step out for our walks. The ambiance feels timeless, as if we've slipped into another era entirely. In these moments, walking through neighborhoods where life happens authentically, I understand why we keep coming back.
Lisbon isn't just a place we visit anymore—it's becoming home. And perhaps more importantly, it's teaching me how to be home within myself again.
What started as expat adventures has evolved into something deeper: a love affair with a city that rewards those willing to look beyond its beautiful surface to discover the vibrant community beneath.