Scouting Portugal Is Like Dating in Your 20s
Exciting, a little chaotic, and you’re constantly weighing red flags against charm. Finding your perfect home base in Portugal is a lot like finding “the one” back in the day. You want chemistry, sure, but you also want stability, shared values—and ideally, a nearby grocery store that sells decent wine.
Portugal is a dream for American expat couples. The lifestyle is slower, the weather is kinder, and the food? Let’s just say you’ll stop missing Costco rotisserie chicken real fast. And when you compare the cost of living in Portugal vs USA, well… let’s just say your dollar stretches like yoga pants on a lazy Sunday. Add in world-class healthcare, easy European travel, and a generally welcoming vibe, and it’s no wonder why expats love Portugal so much. For retirees, the benefits of retiring in Portugal include affordable living, excellent healthcare, and a pace that invites you to linger over lunch.
This guide isn’t ranked—every couple’s match is different. Instead, we’re offering you twelve cities we’ve explored, lived in, or seriously considered. One may just be your perfect fit.
City-by-City Breakdown
Lisbon
Urban, historic, and bursting with life, Lisbon is Portugal’s capital and a magnet for expats seeking big-city buzz with old-world charm. You’ll find excellent public transport, more English speakers than almost anywhere else in the country, and a café scene that could give Paris a run for its pastries. Rob loves walking the Avenida da Liberdade, while Susan’s favorites include the Tile Museum, the miradouro de São Pedro de Alcântara, and grabbing bifanas and ginja shots near Carmo. But with charm comes crowds, and summer tourists can make it feel like you’re living in a pop-up museum. The cost of living is on the high side for Portugal, but still a bargain compared to most U.S. cities.Cascais
Susan’s favorite, and it’s easy to see why. Cascais is the kind of place that looks like a screensaver: ocean views, pastel houses, and palm trees swaying next to seafood restaurants. She loves wandering the old back streets with a gelato from Porto di Mare in hand. Rob’s fond of the harbor—and the Irish Pub with a “husband daycare.” It’s a perfect blend of beach-town serenity and cosmopolitan comfort, with quick train access to Lisbon. The cost of living is higher than Portugal’s average, but the calm, clean streets and walkability make up for it.Porto
Artsy, cozy, and easier on the wallet than Lisbon, Porto draws couples looking for creative vibes and a slower pace. The food scene is top-notch—fresh fish, francesinha sandwiches (a Susan favorite), and port wine tastings with a view of the Ribeira that’ll take your breath away. Rob’s charmed by the (possibly mythical) Harry Potter inspiration scattered through the city. It’s walkable, affordable, and misty in winter—but we’re into that whole moody-river aesthetic. We once found a rental above a bakery with a balcony overlooking the Douro—and briefly questioned whether we were in a Netflix special.Tavira
If you want to retire in Portugal without the beach-party vibe, Tavira is your town. Located in the eastern Algarve, it’s quiet, charming, and known for its preserved architecture and gentle pace. Rob can’t get enough of the waterway and the not-really-Roman bridge. Susan’s a fan of walking through the old town and visiting Castelo de Tavira. The cost of living is refreshingly low, especially if you’ve just unloaded a mortgage back in the States. You might need a car to fully enjoy the area, but the payoff is a slower, sunnier life where your biggest decision is red or white with lunch.Faro
Often overlooked for flashier Algarve towns, Faro is both accessible and authentic. With an international airport right in town, you can hop to other European cities while living minutes from a marina-side café. Rob enjoys the waterfront and wandering the old walled city, while Susan loves entering old town through the main gate and sipping drinks at Restaurante O Castelo. Great seafood, friendly prices, and a small but growing expat scene make this one a stealth favorite.Olhão
Rob’s favorite for a reason. Olhão is a gritty, artsy fishing town with a strong pulse—and he loves every bit of it, even the smelly, dilapidated stuff. Susan adores the maze of cobblestone streets lined with trailing flowers, and taking the water taxi to Ilha da Armona for a relaxing beach walk. It’s affordable, unpretentious, and full of life. Every new Portuguese town we visit feels like opening a vintage record store—surprising, full of character, and sometimes, oddly familiar.Coimbra
Portugal’s university city has more to offer than just academic cred. It’s green, culturally rich, and one of the best places to stretch a dollar—er, euro. Healthcare is top-notch, and housing costs are among the lowest on this list. Rob loves diving into the city’s deep history, while Susan was stunned by the Biblioteca Joanina—it’s Hogwarts-level magical. English is less common here, but that also means a more immersive experience.Évora
Dreamy, sun-drenched, and surrounded by vineyards, Évora feels like a postcard. It’s ideal for couples who want a cultural reset in wine country without the tourist crush. The architecture is stunning, the pace is relaxed, and the summers are hot—like, really hot. Rob’s all about the food and wine here, while Susan was mesmerized by the bone chapel—haunting, but beautiful. If Rome and a sleepy village had a baby, it would be Évora.Braga
Braga flies under the radar, but it shouldn’t. With a mix of history and innovation, it offers a balanced lifestyle at a cost well below Lisbon. Rob appreciates the lack of hills—his knees thank him daily. Susan loved climbing the famous Via Sacra staircase (Rob suffered it). It rains more here, but the community vibe makes up for it. Braga is the introvert’s Lisbon.Lagos
Part beach town, part party town, Lagos manages to keep its authenticity even with the influx of summer tourists. Susan loves the rocky beaches and coastal cliff walks, and Rob’s all in on the ocean-facing views. The food scene is broad and fun—from pub grub to polished plates. In July, it can feel like spring break for grownups, but by fall, the crowds thin and the magic returns.Setúbal
Want Lisbon access without Lisbon prices? Setúbal offers authentic Portuguese life, amazing seafood, and even a dolphin-watching scene. Rob swears by the choco frito (fried cuttlefish), while Susan loves both the food and the bustling Mercado do Livramento. Some parts feel a bit worn, but that’s also part of the appeal. Setúbal is the surf-and-turf of Portugal—raw, beautiful, and surprisingly flavorful.Algés / Cruz Quebrada
Our home base, and a hidden gem. Tucked just west of Lisbon, this riverside neighborhood has a cozy, lived-in feel. There’s a small-town rhythm, neighborhood cafés, and a train that gets you downtown in minutes. Susan loves strolling the Passeio Marítimo and hanging at the Mercado de Algés, while Rob’s fond of the hip local barber shop and the fact that tourists haven’t caught on yet. Living here feels like you’ve discovered the quiet back entrance to Lisbon—a little train, a local café, and a view of the river that beats a screensaver any day.
Need help narrowing the list?
Best for Retiring: Tavira, Évora, Coimbra
Best Base for Exploring Europe: Lisbon, Porto, Faro
Mild Weather Seekers: Cascais, Setúbal, Algés
Tip: The best time to visit Portugal for mild weather is spring and early fall—plenty of sun without the scorch.
Your Perfect City Is Waiting—Pack Curiosity, Not Just Clothes
There’s no one-size-fits-all city, and that’s the beauty of Portugal. We recommend renting before committing, sampling different cities, and yes—eating as many pastéis de nata as your heart desires.
We chose Algés/Cruz Quebrada because it felt like us: calm, close, and just quirky enough. If you’re itching to explore beyond Portugal, the best months to visit Europe from Portugal are April to June and September to October—when flights are affordable and crowds are thinner. Your perfect match might be different.
Exploring Europe from Portugal is like binge watching VH1 in the ‘90s—endless variety, and you’re hooked despite yourself.
