Two Weeks In Portugal: A Journey Through Its Iconic Cities

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Contributor Ali Webb crafts a memorable two-week itinerary in Portugal that offers a mix of culture, history, and culinary delights. 

Portugal, a country no larger than the state of Indiana, had been on our travel bucket list for years. Its mix of vibrant cities, picturesque coastlines, and celebrated wine regions promises a diverse and exciting trip.

From Lisbon’s city streets to the Douro Valley’s lush vineyards and Madeira’s tropical charm, our two-week journey in Portugal took us on a memorable adventure to several destinations filled with wine, delicious local flavors, friendly people, outstanding scenery, and historical sights.

Lisbon: The Heart of Portugal

We started and ended our trip in Portugal’s capital, Lisbon, with its winding cobblestone streets, colorful facades, and sweeping river views. Getting there was easy. TAP Air Portugal offers amazing airfare deals and a nice ride. 

Where We Stayed

We stayed at AlmaLusa Baixa/Chiado, a boutique hotel with stylish, modern decor housed in an 18th-century building. Its prime location on Praça do Município, one of the most emblematic squares of Lisbon, makes it easy to explore the city’s highlights both by foot and with the local rideshare service, Bolt. 

What We Saw

But be prepared to walk many hills. Let me repeat: many hills. We took a walking tour of Lisbon’s historic neighborhoods, such as Alfama, Mouraria, and Baixa.  A friend turned us on to the We Hate Tourism tour group, which promises a small group, off-the-beaten-path experience.

They pointed out all of the landmarks, such as the São Jorge Castle (a national monument and museum), Lisbon Cathedral, and the iconic Praça do Comércio (one of Lisbon’s iconic squares). The tour filled us in on the country’s history, warts and all. We liked their approach so much that we also signed up for their Sinta and Porto tours.

Where We Dined

For lunch, we indulged in the rustic charm of Taberna Sal Grosso, a hidden gem that offers a modern twist on authentic Portuguese recipes. Try the octopus or their slow-cooked pork, accompanied by an excellent selection of Portuguese wines. We sat at the group table and met some interesting fellow adventurers.  

Flor da Laranja is an unmissable dinner spot specializing in Moroccan-inspired dishes and known for its warm ambiance and bold flavors. The redoubtable Rabea, who cooks, serves, cleans, and takes reservations, owns and operates this restaurant. Take her advice and sit back for a wonderful experience.

A Fairytale Escape to Sintra

Sintra, an enchanting escape filled with palaces, lush gardens, and misty forests, is easily accessible by a short train or bus ride from Lisbon. 

Guided by the We Hate Tours guide, we skipped the typical tourist spots and visited the less-crowded Biester Palace, a neo-Gothic marvel surrounded by serene parkland.  You must stop at Casa Piriquita for a traditional travesseiro, Sintra’s puff pastries that are a perfect mid-morning treat.

On our way to the beach, we grabbed a chorizo-stuffed sandwich from Pão Saloio and headed to Guincho Beach, where we enjoyed our lunch while soaking in the Atlantic coastline’s rugged beauty. 

A Week in Madiera: An Island of Natural Wonders and Flavors

During our trip to Portugal, we managed to fit in a week on the island of Madeira, a paradise for food lovers and adventurers alike. We stayed in a rental villa near Funchal, the island’s capital. 

Where We Dined

With foodies in our group, we headed to the Mercado dos Lavradores, the city farmers’ market but weren’t overly impressed. We did love visiting Portugal Farm Experiences, which provides farm-to-table cooking classes. Our charming host, Valter, took us on a tour of his small organic farm, where we picked a few yummy items from the garden and then enjoyed a lovely lunch that he prepared—traditional Portuguese roasted beef on a skewer. Definitely worth a visit…and beware of the potent poncho punch to start!

For another memorable dining experience, we stopped at Vila do Peixe in Câmara de Lobos, a restaurant famous for its fresh, grilled seafood. Another must-visit spot is Laranjinha, where you can indulge in local dishes while enjoying views of the surrounding hills and coast.

Where We Sipped

Wine enthusiasts shouldn’t miss the chance to sample Madeira wine, a fortified wine with a rich history dating back to the Age of Exploration. We did a wine tasting and tour to learn about the unique production process that gives Madeira wine its distinctive flavor profile. 

A pro tip is that it does taste better as it ages. A favorite of America’s Founding Fathers, Madeira wine maintains its drinkability even after the bottle is opened.

Where We Went

While in Madeira, we enjoyed a leisurely walking tour of Funchal. We began in the historic old town with its cobblestone streets, then took a stroll along the waterfront, where you’ll find the marina and plenty of cafes perfect for a final glass of wine before your journey ends. 

For a final cultural experience, visit the Monte Palace Tropical Garden, where nature and art meet in a stunning hillside setting. Don’t miss the funicular down to the beach.

We did try the Hop On/Hop Off Bus in Maderia to get an overview of the island. Maybe it was us, but I don’t recommend it as a way to see the island. The route (and ride) was too frenetic to be enjoyable.

Visiting Porto: The Capital of Port Wine

From Madiera, we flew north to Porto, a city known for its riverfront charm and world-class port wine. We wandered through the UNESCO-listed Ribeira district, filled with narrow streets, colorful houses, and riverside cafes.

Don’t miss the chance to visit the famous port wine cellars in Vila Nova de Gaia, where you can tour the storied wineries and sample a variety of aged port, another fortified wine from the region. 

We loved the vast market, Mercado do Bolhão. What a great stop for souvenirs and lunch! We also discovered a restaurant gem, Societa46, which served, among other treats, colorfully sauced ravioli.

Porto is a lovely city that feels much more manageable than Lisbon regarding crowds and congestion.

Exploring the Douro Valley: Portugal’s Wine Country

Our final Portuguese adventure was to venture from Porto into the Douro Valley, a scenic region defined by terraced vineyards and bisected by the Douro River. This area is the heart of Portugal’s wine production, producing exceptional still wines. 

Our private guided tour with Joao and his company, Operto and Douro Moments, took us to some of the area’s best wineries. The company is an 11-year-old family-run business with great connections in the valley.  

At our first stop, Quinto do Cume, we were invited to help stomp grapes with our bare feet. We also visited Quinto de Tourais, a multiple-generation winery where we tasted the really good stuff, a 30-year-old port.

A Farewell Toast to Portugal

We took a train back to Lisbon and reminisced about all our experiences.  From Lisbon’s lively food scene to the vineyards of the Douro Valley and the island charm of Madeira, Portugal offers an unforgettable mix of culture, history, and flavors. 

Whether sipping port in Porto, tasting Madeira wine on a tropical island or sampling regional and local specialties, your journey will be filled with delicious discoveries and lasting memories.

*Contributor Ali Webb, PhD is adjunct faculty at the University of Michigan and Columbia University. Her long career in strategic communications has offered her many opportunities for domestic and foreign travel. She wrote a bi-monthly Sunday travel column, The Indulgent Traveler, for a Gannett daily in Michigan and now contributes to other travel websites. 

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