I finally made it to Lisbon Portugal and discovered more flavor, feeling, and fascinating history than I ever expected. This isn’t your average travel guide. Here’s what it’s really like to explore Lisboa Lisbon for the first time, with day trips to Sintra and Cascais along the way.
Day 1: Diving into Lisbon’s Heart
After landing just before 3 p.m., we jumped into an Uber and within 15 minutes were in the heart of the city. Jet-lagged but excited, we kicked off our Lisbon adventure with a local food tour.
Lisbon’s central districts are a fascinating blend of old and new. As one of Europe’s oldest capitals, Lisbon predates Rome by centuries, with evidence of settlements dating back to 1200 BCE. The city survived one of history’s most devastating earthquakes in 1755, which almost completely destroyed the medieval city and led to the distinctive grid-pattern reconstruction of the Baixa district.
Pro Tip: Book a food tour for your first day. It’s the perfect introduction to the city’s culture, cuisine, and layout.
Our first taste of Lisbon was literal – Super Bock beer paired with bifana, a delicious pork sandwich marinated in wine and garlic. Our guide Cate showed us popular sights and local food spots throughout central Lisbon.
Portuguese cuisine reflects the country’s seafaring history, with influences from former colonies in Africa, Asia, and South America. Dishes like bacalhau (salt cod) appear in hundreds of variations and tell the story of Portugal’s maritime empire and Catholic traditions.
Tour Recommendation: Undiscovered Lisbon Food Tour with Eating Europe – Our guide Cate was fantastic, offering insider knowledge and taking us to authentic spots most tourists never find.
We sampled Ginjinha (cherry liqueur) and discovered one unavoidable truth about Lisbon: the streets are beautiful but steep. The cobblestone paths and stairs will give you the best leg workout of your life! Worth every step though for the stunning architecture and views.
As evening fell, we experienced our first fado Lisbon performance. The soulful Portuguese music filled the small venue as we enjoyed bacalhau à Brás (a traditional cod dish) and ended with warm, freshly baked pastries.
Fado (meaning “fate” in Portuguese) emerged in the early 19th century in working-class neighborhoods like Alfama and Mouraria. This UNESCO-recognized musical tradition expresses “saudade” – a uniquely Portuguese concept of longing and melancholy. The haunting vocals accompanied by Portuguese guitars tell stories of the sea, lost love, and hardship, embodying the Portuguese soul.
Day 2: Exploring Lisbon’s Hills and History
Morning: Electric Bike Tour
Lisbon what to do when faced with the famous seven hills? Take an electric bike tour! Our guide Antonio led us through courtyards, steep alleyways, and hidden viewpoints most tourists never see.
Lisbon earned its nickname “City of Seven Hills” from the ancient seven hills of Rome. These hills have shaped the city’s development, resulting in its unique urban landscape of winding streets, steep staircases, and elevators connecting different levels. The hills also create the city’s famous miradouros (viewpoints) offering breathtaking panoramas.
We covered impressive ground without breaking a sweat:
- Ancient Roman aqueducts
- Beautiful green parks and bridges
- Baixa Lisbon (downtown district)
- Avenida da Liberdade (luxury shopping street)
- Commerce Square
The Águas Livres Aqueduct, completed in 1748, is an engineering marvel that once supplied Lisbon with fresh water. Baixa, with its elegant grid pattern, was completely rebuilt after the 1755 earthquake using innovative anti-seismic architecture. Commerce Square (Praça do Comércio) was once the royal palace site and later became the commercial gateway to the city, symbolizing Portugal’s maritime power.
Three hours on bikes showed us more of Lisbon than we could have seen in a full day on foot.
Tour Recommendation: Lisbon Go 7 Hills Electric Bike Tour – Antonio was an incredible guide who knew all the shortcuts and viewpoints. The electric bikes made Lisbon’s infamous hills a breeze!
Afternoon: Slave Trade Walking Tour
One of the best ways to understand a city is through its history. We joined a powerful three-hour walking tour focused on Lisbon’s role in the transatlantic slave trade, led by Rui from Mozambique.
The tour took us through key neighborhoods including Alfama Lisbon, one of the city’s oldest districts. We traced routes through historic areas, learned how wealth from enslaved Africans shaped Lisbon’s architecture, and saw how art and monuments reflected both pride and pain.
Alfama survived the 1755 earthquake that devastated most of Lisbon, preserving its Moorish influence with narrow, maze-like streets designed to create natural air conditioning and confuse invaders. Once a poor fishermen’s quarter, it’s now known for authentic fado venues and traditional Portuguese life. The neighborhood’s name comes from the Arabic “Al-hamma,” meaning “hot springs” or “baths,” reflecting its Moorish past.
Portugal was the first European country to engage in the transatlantic slave trade in the 15th century and the last to abolish slavery in its colonies in 1869. This dark chapter fundamentally shaped Lisbon’s wealth, architecture, and cultural identity – aspects often overlooked in traditional tourism.
This sobering experience provided great insight into the origins and impact of the slave trade that enhanced our understanding of Lisbon’s past.
Tour Recommendation: Half Day Historical Walking Tour about the Slave Trade in Lisbon – Our guide Rui is a true academic who brings depth and nuance to this often overlooked aspect of Lisbon’s history.
Evening: Candlelit Fado Dinner
For dinner, we immersed ourselves deeper in fado Lisbon culture with a candlelit performance. Between each course, fado singers filled the room with raw emotion, backed by masterful guitarists. It felt like a conversation with Lisbon’s soul – the perfect way to end our second day.
Traditional fado houses (casas de fado) like this one are essential cultural institutions where Portugal’s musical heritage is preserved and passed down. In these intimate venues, you’ll often find multi-generational performers, with younger artists learning from veterans in an unbroken chain dating back to the early 19th century.
Day 3: Day Trip to Sintra and Cascais
Our day started bright and early for one of the most anticipated adventures – a day trip from Lisbon to Sintra and Cascais, the Portuguese Riviera.
Tour Recommendation: Sintra & Cascais Small Group Day Trip from Lisbon – Our guide Paolo was knowledgeable and personable, making this comfortable small-group tour one of the highlights of our trip.
Sintra Palace
Pro Tip: Get to Sintra early! When we arrived, a line was already forming 30 minutes before opening.
Sintra is magical – nestled in the mountains, five degrees cooler than Lisbon, and full of romantic architecture and misty, eucalyptus-scented air. The palace, once the summer home of Portuguese royalty, features incredible details from tiled walls to sprawling gardens.
Sintra has been a royal sanctuary since the Middle Ages due to its cooler microclimate and lush landscape. The town became a center for Romantic architecture in the 19th century when Ferdinand II transformed a ruined monastery into the whimsical Pena Palace. Lord Byron called Sintra “glorious Eden,” inspiring generations of poets and artists. In 1995, UNESCO recognized the entire cultural landscape as a World Heritage site – the first in Europe to receive this designation for the harmonious relationship between natural and built environments.
After exploring the palace, we wandered through the charming town of Sintra itself, with its narrow streets and famous pastries.
Cabo da Roca
Next stop: the westernmost point of continental Europe. The dramatic coastal views here are absolutely stunning – rocky cliffs dropping into the Atlantic Ocean. Just be prepared for the swarms of gnats if you visit!
Cabo da Roca sits 140 meters above the Atlantic at the westernmost edge of mainland Europe – a place the Romans called “where the land ends and the sea begins.” This windswept promontory was once considered the edge of the known world. A stone monument marks this geographic significance with an inscription from Portuguese poet Luís de Camões. Before GPS navigation, this dramatic lighthouse-topped cape was vital for sailors determining their position along Portugal’s treacherous coast.
Cascais
From Lisbon to Cascais is only about 30-40 minutes, but it feels like entering another world. Often called the Portuguese Riviera, Cascais features white buildings, tropical vibes, and beautiful beaches.
Cascais transformed from a sleepy fishing village to an aristocratic playground when the Portuguese royal family began summering here in the late 19th century. European nobility and elites followed, building elegant villas and establishing it as the Portuguese Riviera. During World War II, Cascais became a glamorous haven for exiled European royalty and wealthy refugees, including the King of Italy and various aristocrats escaping the conflict. The town’s neutral status during the war helped preserve its architecture and affluent character. Today, its combination of historic charm, golden beaches, and upscale marina attracts visitors seeking a refined coastal experience.
We enjoyed fresh seafood at Sr. Manuel – sautéed prawns with chili sauce, fresh vegetables, and refreshing lemonade – while taking in the coastal atmosphere.
Last Hours in Lisbon
For our final moments in Lisbon, we took the famous yellow tram up the hill for one last breathtaking view before ending with dinner at Oficina do Duque in Bairro Alto Lisbon, a vibrant neighborhood known for its nightlife.
Lisbon’s iconic yellow trams (particularly the historic Tram 28) began operating in 1873 and continue to serve as practical transportation while offering visitors a quintessential Lisbon experience. These vintage Remodelado trams, with their wooden interiors and brass fixtures, navigate streets too narrow and hills too steep for modern vehicles.
Bairro Alto (Upper District) dates back to the 16th century and sits atop one of Lisbon’s seven hills. By day, it’s a quiet residential neighborhood with traditional shops and cafés. As night falls, it transforms into Lisbon’s most energetic nightlife district, with dozens of bars, fado houses, and restaurants spilling onto the narrow streets. During the Age of Discovery, it was home to writers and artists; today, it maintains its bohemian character while balancing tradition with trendy establishments.
Where to Stay: Hotels in Lisbon
We stayed at the Intercontinental Lisbon, a sophisticated hotel offering stunning views of the city and Eduardo VII Park. Its central location made it easy to explore while providing a luxurious retreat after our days of sightseeing.
Other excellent hotels in Lisbon to consider:
- Baixa Lisbon area: Perfect for first-time visitors, centrally located near major attractions. This downtown district was completely rebuilt in a grid pattern after the 1755 earthquake, featuring elegant 18th-century buildings, grand plazas, and pedestrian shopping streets.
- Alfama Lisbon: Stay in converted historic buildings for authentic charm. The oldest neighborhood in Lisbon predates the Moorish occupation and survived the 1755 earthquake, preserving its medieval layout of narrow winding streets and small squares.
- Bairro Alto Lisbon: Ideal for those who want nightlife at their doorstep. This 16th-century district transforms from a quiet daytime neighborhood into Lisbon’s most vibrant nightlife area after dark.
- Chiado: Upscale shopping and dining with elegant hotel options. This sophisticated cultural district was the intellectual center of Lisbon in the 19th century, home to famous literary cafés and theaters frequented by Portuguese writers and artists.
Lisbon Places to Visit That We Missed
Three days wasn’t enough to see everything this remarkable city offers. On my next trip, I’ll make sure to visit:
- Belem Tower Lisbon – The iconic 16th-century fortification built during the Age of Discovery that served as both a defensive structure and ceremonial gateway for explorers departing on voyages. This UNESCO World Heritage site represents Manueline architecture at its finest, with maritime motifs and historical significance as a symbol of Portugal’s naval power.
- Jerónimos Monastery – A masterpiece of Manueline architecture and UNESCO World Heritage site built to commemorate Vasco da Gama’s successful voyage to India. The monastery’s ornate cloisters and maritime-themed decorations celebrate Portugal’s Age of Discovery wealth and power.
- LX Factory – A 19th-century industrial complex transformed into Lisbon’s creative hub with shops, restaurants, and street art. This revitalized factory district represents Lisbon’s contemporary renaissance, blending historical industrial architecture with modern creativity.
- Time Out Market – Food hall featuring the city’s best chefs housed in the historic Mercado da Ribeira. This culinary destination showcases Portugal’s gastronomic revival, bringing together traditional recipes and innovative cooking in a communal dining experience.
Final Thoughts on Lisbon Travel
Lisbon was everything I didn’t expect and so much more. From the hills to the soulful fado music and delicious pastries, it surprised me at every turn. Whether you’re a history buff, a foodie, or someone looking for a laid-back vibe, Lisbon’s charm is undeniable.
Three days in Lisboa Lisbon gave us a taste, but I’m already planning my return to this captivating city. If you’re considering travel to Lisbon Portugal, don’t hesitate – just pack comfortable shoes!
Have you visited Lisbon? What were your favorite spots? Share in the comments below!
Enjoy!
Antoinette | Frolic & Courage
