Lost in Lisbon: A 5-Day delightful Lisbon Itinerary to Experience the Soul of Portugal

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As I was getting ready for my trip to Lisbon, I was perusing a few videos online, and one video struck me when it said, Lisbon is ‘colourful organized chaos‘, and when we reached Lisbon, I realised it couldn’t be more apt.

5 Day Lisbon Itinerary Highlights

There is a lot of walking involved in Lisbon. Lisbon’s hilly landscape is one of its defining characteristics, giving the city its unique topography and stunning viewpoints (miradouras). There is a lot of walking involved, I usually used Bolt to get to the top of hills. It was cheaper than Uber. Navigating these hills is an essential part of exploring Lisbon, and it offers a chance to discover the city’s hidden corners, vibrant neighbourhoods and breathtaking panoramic views.

From the medieval alleys of Alfama to the artistic streets of Graca and the trendy vibes of Bairro Alto, each hill offers a unique experience that adds to the rich tapestry of Lisbon’s character. Whether you’re wandering through historic districts, enjoying a coffee at a local cafe, or marvelling at the city’s beauty from a miradouro (viewpoint), Lisbon’s hills offer a journey that are as rewarding as it is memorable.

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Lisbon is well-connected internationally, and the Lisbon Portela Airport (Aeroporto Humberto Delgado) is the main gateway. It’s located just a short distance from the city center, making transportation to your accommodation relatively easy. Public transportation options, such as taxis, metro and buses, are available from the airport to various parts of the city.

Side Note (Lost Baggage) – We were travelling from Barcelona to Lisbon with Vueling Airlines. Our luggage arrived in Lisbon after we already left the city, and it’s been over a year and declared officially lost. After almost 6 months of following up with the airlines and getting nowhere, we finally started a process claim with Reclamio. Will update once I get any notifications if our claim is successful.

We had lost our luggage but found out spirits the moment we got out of the airport. Moving to Lisbon’s historical district with some superb views along the way reminded me that sometimes bad things happen while travelling, we just have to make the most of it 🙂

Arrive in Lisbon and settle into your chosen accommodation, ideally located in the historic heart of the city, such as Alfama or Baixa districts.

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Start your journey with a leisurely exploration of the Alfama district. Meander through its maze-like streets, adorned with colorful tiles and hanging laundry. Immerse yourself in the local atmosphere as you discover cozy cafés, traditional Fado houses, and charming boutiques.

Enjoy breathtaking views of the Tagus River and Alfama’s rooftops at the Miradouro de São Pedro de Alcântara. It’s located near the Elevador da Glória funicular and the Baixa-Chiado metro station. As you step onto the miradouro, you’ll be greeted by a mesmerizing panorama that stretches from the Baixa district to the São Jorge Castle, with the Tagus River glistening in the distance. The view showcases Lisbon’s colorful rooftops, historic buildings, and the breathtaking São Vicente de Fora Church. At the center of the miradouro stands a statue of Saint Peter, the patron saint of fishermen. The statue pays homage to Lisbon’s maritime heritage.

For those into shopping, the Feira da Ladra flea market is a treasure trove of antiques, crafts, and unique finds. Haggle for vintage treasures and souvenirs. Arrive in the late afternoon at the Miradouro da Graca to catch a breathtaking view over the city. It’s a perfect spot for relaxation and reflection.

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As the afternoon sun casts a warm glow, make your way to Sao Jorge Castle. Climb the ancient walls for panoramic views of Lisbon’s rooftops and the glittering Tagus River. Perched majestically atop a hill overlooking the city of Lisbon, São Jorge Castle stands as a living testament to the rich history and cultural tapestry of Portugal.

This iconic fortress, with its medieval walls, archaeological sites, and commanding views, offers visitors a journey through time and a glimpse into the city’s past. The reconstructed Moorish quarter allows visitors to step back in time and experience the daily life of the castle’s former residents. Wander through narrow streets, courtyards, and houses.Consider using the castle’s audio guide, available in multiple languages, to enhance your understanding of its history and significance.

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Experience wine tasting in a unique setting at The Old Pharmacy Wine Bar—an old pharmacy turned wine bar. Sip on Portuguese wines paired with tapas.

Indulge in an authentic Fado experience in the heart of Alfama. Choose a traditional Fado restaurant and let the haunting melodies and heartfelt lyrics transport you back in time. Savor a delicious Portuguese dinner as you’re serenaded by the soulful tunes. Maria Catita has some excellent food.

Catch an epic sunrise at the Miradouro das Portas do Sol, quite possibly the best viewpoint in all of Lisbon. Miradouro das Portas do Sol, which translates to “Viewpoint of the Sun Gates,” is appropriately named, as it basks in the warm embrace of Lisbon’s sunlight. This scenic spot is perched on a hilltop, offering an unobstructed view of the historic Alfama district—a neighborhood steeped in history, charm, and vibrant local culture.

The miradouro is not just about the view—it’s also about the atmosphere. As you stand there, you’ll feel the essence of Alfama all around you. The soft whispers of Fado music might reach your ears, and the scent of traditional Portuguese cuisine might tickle your senses.

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Just a short walk away is the Lisbon Cathedral, a historic landmark that holds centuries of stories within its walls. Also known as Se de Lisboa, it stands as a remarkable testament to the city’s rich history, architectural splendor, and spiritual significance. With its grand facade, awe-inspiring interiors, and centuries-old stories, the cathedral offers a captivating journey through time. As you step inside the cathedral, the hushed atmosphere and filtered light create a sense of serenity and reverence.

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From here, head to the Carmo convent and the Terracos do Carmo. Witness the intricate ironwork and elegant design of the Santa Justa Elevator, a neo-Gothic masterpiece that connects the lower and upper parts of the city.

Silently standing as a poignant testament to the passage of time, the Carmo Convent, or Convento do Carmo, embodies both the beauty of architectural heritage and the resilience of Lisbon’s spirit. This hauntingly beautiful ruin, situated in the heart of the city, holds within its walls a profound history that spans centuries. The main nave of the church, though open to the sky, retains the grandeur of its original design. The intricate stonework and towering arches create a sense of reverence and wonder. Scattered throughout the ruins are chapels and altars adorned with religious art and sculptures, providing insights into the spiritual life of the convent.

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As you step onto the Terraços do Carmo, you’ll be greeted by breathtaking panoramic views that encompass both historic and modern elements of Lisbon. This charming rooftop terrace, situated atop the Carmo Convent, allows visitors to unwind amidst lush greenery while marveling at the surrounding architectural beauty. Witness the intricate ironwork and elegant design of the Santa Justa Elevator, a neo-Gothic masterpiece that connects the lower and upper parts of the city.

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Lisbon Itinerary, Things to do in Lisbon, What to do in Lisbon, Lisbon Miradouros, Lisbon Viewpoints, Lisbon Day Trip, Lisbon Travel Itinerary, Lisbon Travel Plan, Lisbon Holiday, Lisbon Blog Post

As you take in the architecture, street performances, and bustling activity, you’re immersing yourself in a world where history meets modernity, creating moments that linger in your memory long after you’ve walked its vibrant path.

Next up, head to the Belem district, a treasure trove of historical landmarks. Visit the iconic Belem Tower (Torre de Belém), a sentinel at the river’s edge. As you stand beneath its elegant arches and ascend its walls, you’re retracing the steps of explorers who once embarked on epic journeys from Lisbon’s shores. Whether you’re soaking in the riverside views, exploring nearby cultural sites, or simply admiring the craftsmanship of the tower’s details, you’re engaging with a legacy that has shaped both Lisbon’s identity and the world’s history.

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Stroll along the promenade that offers breathtaking views of the Tagus River and the iconic 25 de Abril Bridge. Marvel at the intricate details of the Jeronimos Monastery. As you marvel at the ornate façade, meander through cloistered walkways, and gaze upon the final resting place of Vasco da Gama, you’re immersing yourself in a narrative that spans centuries. This monastery not only honors the legacy of Portugal’s past but also invites you to contemplate the boundless human quest for knowledge, discovery, and cultural enrichment.

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While in the Belem district, delight your taste buds with the famous Pastéis de Belém.

As the evening approaches, rush to the Miradouro de Santa Catarina at sunset, where the beauty of Lisbon’s skyline is illuminated by the warm hues of the setting sun. As the day draws to a close, this captivating viewpoint transforms into a canvas of colors, offering a mesmerizing spectacle that captures the essence of the city’s charm. Aim to arrive at the Miradouro de Santa Catarina about 30 to 45 minutes before sunset to secure a good spot.

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Lisbon Itinerary, Things to do in Lisbon, What to do in Lisbon, Lisbon Miradouros, Lisbon Viewpoints, Lisbon Day Trip, Lisbon Travel Itinerary, Lisbon Travel Plan, Lisbon Holiday, Lisbon Blog Post

Consider dressing slightly more formal to match the atmospheric setting and show respect for the performers. Fado is an emotional journey, a bridge between the past and the present, and a testament to the power of music in conveying profound human emotions. As you sit in the cozy venue, surrounded by the haunting melodies and heartrending vocals, you’re invited to step into the stories and sentiments of Portugal’s soul. Fado captures the essence of what it means to be human, to experience love, loss, joy, and longing, and it does so in a way that transcends language and culture.

By experiencing Fado, you’re not just attending a performance; you’re immersing yourself in a cultural tradition that has touched hearts for generations, making it an unforgettable part of your journey through Lisbon.

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Head directly to the Commerce Square (Praça do Comercio), Lisbon’s Grand Maritime Gateway, early morning. Even though it is nearer to the Rua Augusta, I found it best enjoyed in the soft light of the morning sun and relatively quieter atmosphere before the crowds arrive.

This expansive square is flanked by majestic buildings, offers stunning waterfront views, and exudes an air of significance that is palpable as you explore its rich heritage. Admire the equestrian statue of King Jose I, a symbol of Lisbon’s maritime history and the prosperity of the Age of Exploration. Marvel at the impressive yellow buildings that line the square, characterized by their grand arcades and intricate designs.

Often unnoticed tip – Observe the mosaic pattern on the ground of Commerce Square, designed to mimic the patterns of waves as a tribute to Portugal’s maritime history.

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Head to the Lisbon Story Center and immerse yourself in engaging audiovisual presentations that trace the city’s evolution from its earliest days to the present. Learn about the foundation of Lisbon and its evolution from a bustling harbor to a cultural hub. Gain insights into the devastating 1755 earthquake and the subsequent reconstruction of the city. From here, head to (you guessed it, another Miradouro) Miradouro da Senhora do Monte, a breathtaking viewpoint.

It’s finally time to hop onto the beloved Tram 28 for a nostalgic voyage through the historic heart of Lisbon. This iconic tram route, beloved by locals and tourists alike, takes you on a winding journey through narrow streets, picturesque neighborhoods, and past some of the city’s most famous landmarks. Hop on and let’s explore the enchanting sights and stories that Tram 28 has to offer.

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Purchase your tram ticket in advance or consider using the Viva Viagem card, which offers convenience for multiple forms of public transportation.

Start at Martim Moniz Tram Stop and try to secure a seat by the window for the best views. Pass through Graça, a charming residential area with panoramic viewpoints and a serene ambiance. Wind through the labyrinthine streets of Alfama. Get off the tram at Miradouro da Senhora do Monte to enjoy panoramic vistas of Lisbon’s rooftops and the river.

Enjoy a leisurely evening stroll through Barrio Alto, one of Lisbon’s most iconic neighborhoods that pulsates with bohemian energy, artistic flair, and vibrant nightlife. This historic district is a melting pot of cultures, creativity, and community, offering a captivating blend of daytime exploration and nighttime revelry. Stroll along Bairro Alto’s narrow streets lined with colorful buildings adorned with intricate tiles. Discover boutique stores, vintage shops, and quirky art galleries that showcase the neighborhood’s artistic spirit.

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Bairro Alto truly comes alive in the evening, so plan to spend your night exploring its lively streets and social scenes. Experience the soulful notes of Fado music at one of Bairro Alto’s intimate Fado houses. Dive into Bairro Alto’s legendary nightlife by hopping between its countless bars and pubs.

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If you are into parties, Lisbon has an active nightlife. Even though Barrio alto shuts down around 1 am, there are lots of parties happening till early morning. I had heard a lot about Pink Street but it was extremely disappointing. You won’t miss much if you give it a miss unless you want to wander there on. anevening and have some beers.

Day 4 of your Lisbon itinerary begins at LX Factory, an industrial-chic district that brims with creativity. Once an industrial complex, LX Factory has been transformed into a dynamic space where art, design, gastronomy, and innovation flourish. Explore art galleries, designer shops, and enjoy a leisurely coffee at one of the trendy cafes.

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Admire the vibrant street art and murals that adorn the walls, adding an artistic touch to the surroundings. Explore eclectic bookstores, galleries, and studios that showcase the work of local artists and designers. Indulge in delectable cheesecakes at LXeese Cake Factory.

Dive into Lisbon’s contemporary art scene at the Berardo Museum, showcasing an impressive collection of modern and contemporary art.

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Venture through an empty Pink Street and head for lunch at the Time Out Market promises a culinary voyage through Portugal’s flavors. Nestled in the vibrant Cais do Sodre district, this market offers a delightful blend of flavors, aromas, and experiences that showcase the city’s rich gastronomic landscape. Explore the various food stalls to choose from an array of Portuguese and international dishes.

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Time Out Market Lisbon isn’t just a place to dine—it’s a culinary adventure that takes you on a tour of Lisbon’s diverse flavors and tastes. Every stall represents a unique chapter of Lisbon’s culinary story. As you immerse yourself in the bustling ambiance, savor the aromas, and share conversations over delicious meals, you’re not just experiencing a meal—you’re becoming a part of the vibrant culinary tapestry that defines Lisbon’s gastronomic identity. Time Out Market is a celebration of food, community, and culture, where every bite is a journey and every meal is a memory to cherish.

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Afterward, embark on a relaxing Tagus River cruise. Admire the city’s skyline from a new perspective as you glide along the water, taking in landmarks like the Monument to the Discoveries and the 25 de Abril Bridge.

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Unwind in the evening with a delightful Portuguese wine tasting experience. Visit a local wine bar or attend a guided tasting session, allowing your taste buds to savor the unique notes and aromas of Portugal’s finest wines.

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Embark on a day trip to Sintra, a place straight out of a fairy tale. Begin your journey by visiting the Palácio Nacional de Sintra, an architectural marvel with whimsical conical chimneys and a rich history dating back to Moorish times. Explore the stunning Pena Palace, a riot of color perched atop a hill, and uncover the mystical pathways of Quinta da Regaleira.

Choose from the local restaurants in Sintra to indulge in Portuguese cuisine. Don’t miss the opportunity to try the iconic pastéis de Sintra. Stroll through the cobbled streets of Sintra’s town center, where you can explore local shops, cafes, and absorb the town’s relaxed atmosphere.

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From Sintra, venture to the charming coastal town of Cascais. If you’re driving, head south from Sintra towards Cascais via the N9-1 or A5 highway. The scenic drive takes approximately 30-40 minutes. Another option is to take the scenic train ride from Sintra to Cascais, passing through lush landscapes and offering glimpses of the Atlantic Ocean. The train journey takes around 40-50 minutes.

Stroll along the promenade, feel the sand between your toes on the beaches, and explore the quaint streets dotted with boutiques and seafood restaurants. Stop at the Boca do Inferno, a dramatic cliff formation that offers breathtaking views of the Atlantic Ocean. Choose from the array of seaside restaurants in Cascais to enjoy fresh seafood and coastal views. Wind down your day by relaxing on Cascais Beach and watching the sunset.

Head back to Lisbon.

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Lisbon is a paradise for food lovers, offering a wide array of dishes that reflect the city’s rich culinary heritage. From traditional Portuguese delicacies to contemporary fusion creations, there’s something for every palate. Here are some of the best foods to eat in Lisbon to truly savor the essence of this vibrant city:

Pasteis de Nata – Indulge in the iconic Portuguese custard tart, the Pastel de Nata. These flaky pastries with a creamy custard filling are a must-try treat that captures the essence of Portuguese baking.

Bacalhau à Brás – Savor the traditional Bacalhau à Brás, a dish made with salted codfish, scrambled eggs, and crispy matchstick fries, all seasoned to perfection with parsley and black olives.

Amêijoas à Bulhão Pato – Enjoy a plate of Amêijoas à Bulhão Pato, a flavorful dish of clams sautéed with garlic, olive oil, and fresh coriander. It’s a perfect representation of the sea’s bounty in Portuguese cuisine.

Bifana – Sink your teeth into a Bifana, a delicious sandwich featuring seasoned pork loin marinated in a spicy sauce and served in a crusty roll.

Caldo Verde – Warm up with Caldo Verde, a comforting traditional soup made with kale, potatoes, onions, and Portuguese chouriço sausage.

Grilled Sardines (Sardinhas Assadas) – Visit during the summer months and relish in the taste of Grilled Sardines, a seasonal delicacy that’s typically enjoyed during Lisbon’s festive Santo António celebrations.

Cozido à Portuguesa – For a hearty meal, try Cozido à Portuguesa, a stew featuring an assortment of meats, sausages, and vegetables, all simmered together to create a flavorful and hearty dish.

Açorda de Marisco – Indulge in Açorda de Marisco, a seafood bread stew made with crusty bread, fresh seafood, herbs, and poached eggs, creating a unique blend of textures and flavors.

Chouriço Assado – Experience Chouriço Assado, a type of smoked sausage that’s often grilled and served as a simple yet delicious snack.

Arroz de Pato – Delight in Arroz de Pato, a rich and hearty dish made with duck and rice, cooked together to create a flavorful and satisfying meal.

Francesinha – While not originally from Lisbon (it’s a specialty from Porto), Francesinha is a beloved sandwich made with layers of cured meats, steak, and cheese, topped with a spicy tomato sauce and served with fries.

Petiscos – Embrace the Portuguese tapas-style dining with Petiscos, a variety of small dishes that can include cheeses, cured meats, olives, and other delights.

Chouriço a Bombeiro – Experience the fiery flavors of Chouriço a Bombeiro, where Portuguese sausage is flambéed in aguardente (a type of brandy) for a truly memorable taste.

Queijadas de Sintra – While not technically in Lisbon, these Sintra pastries are a must-try. Queijadas de Sintra are small, sweet cheese tarts that are a delightful treat.

Ginja Liqueur – End your meal with Ginja, a Portuguese cherry liqueur often served in chocolate cups. It’s a sweet and slightly tart digestif that’s popular among locals and visitors alike.

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  • Lisbon Pass: Consider purchasing the Lisboa Card, which provides unlimited access to public transportation, museums, and discounts at various attractions.
  • When to Visit Lisbon: Spring (March to May) and Fall (September to October) offer pleasant weather and fewer crowds. Summers can be hot and crowded, while winters are mild but rainy.
  • Where to Stay in Lisbon: Opt for accommodations in the Baixa, Chiado, or Alfama districts for easy access to major attractions.
  • Budget Eateries: Look out for “Tascas” – local Portuguese eateries offering affordable and authentic dishes.
  • Language: While many locals speak English, learning a few basic Portuguese phrases can enhance your experience

Before bidding Lisbon farewell, take some time to collect last-minute souvenirs and gifts. Wander through local markets, shops, and boutiques, ensuring you bring a piece of Lisbon’s magic back home with you. I got this really cute Lisbon Tram souvenir and it always reminds me of the wonderful few days I was lucky enough to spend here.

Lisbon’s charm lies in its ability to effortlessly blend tradition and modernity, inviting travelers to discover its hidden corners and vibrant soul. As your 5 day Lisbon itinerary comes to a close, pack your bags with cherished memories and the echoes of Fado melodies. Depart from your accommodation, knowing that the heartwarming spirit of Lisbon will forever remain a part of your wanderlust-filled soul.

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