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Crafted atop seven hills over centuries, Lisbon is home to cobbled lanes, castles in the clouds and maritime monuments that pay lasting tribute to Portuguese explorers like Vasco da Gama who changed the world. You'll have a choice of excursions today.
1) City sightseeing in Lisbon; discover landmark places steeped in history, including Eduardo VII Park, Trade Square, the Monument to the Discoveries, and Jeronimos Monastery where Vasco da Gama and Portugal's kings are buried.
2) A robust Lisbon walking tour of the city's terraces for those seeking a more active walk.
3) Visit the town of Sintra for a visit to Sintra National Palace, the best preserved medieval residence in Portugal and a UNESCO World Heritage Site. Enjoy some free time in Sintra before driving to the seaside town of Cascais for a guided walk in the town's center and lunch before returning to Lisbon.
48 Tips I Wish I Knew Before Visiting Lisbon
Lisbon is a city of light, legends, and layers—where ancient ruins, pastel-colored buildings, and the scent of grilled sardines mingle on breezy hilltops. As one of Europe’s oldest capitals, Lisbon’s story stretches from Phoenician traders to Roman settlers, Moorish rulers, and the Age of Discoveries, when Portuguese explorers set sail to map the world.
🏛 A City Shaped by Time
Lisbon was nearly destroyed by the 1755 earthquake, followed by a tsunami and fires. The city’s rebirth gave rise to the elegant Baixa Pombalina district, with its grid layout and neoclassical architecture. Today, Lisbon is a vibrant blend of old-world charm and modern energy.
📍 Must-Visit Attractions in Lisbon
Jerónimos Monastery: A Manueline masterpiece and resting place of Vasco da Gama.
Belém Tower: A riverside fortress that once guarded the gateway to the Atlantic.
St. George’s Castle (Castelo de São Jorge): Offering panoramic views and Moorish history.
Alfama District: The oldest neighborhood, with winding alleys, fado music, and hidden courtyards.
Rua Augusta Arch: A triumphal arch celebrating Lisbon’s post-earthquake rebirth.
Carmo Convent: A hauntingly beautiful roofless church left as a reminder of the 1755 quake.
MAAT & Calouste Gulbenkian Museum: For lovers of modern art and world-class collections.
Tram 28: A vintage yellow tram that winds through the city’s most iconic neighborhoods.
🌊 Beyond the City
Sintra: A fairytale town of palaces and misty forests, just a short train ride away.
Cascais & Estoril: Coastal escapes with beaches, seafood, and charm.
Lisbon is a city that invites you to wander—up steep hills, through tiled passageways, and into cafés where time slows down. If you’d like, I can help you build a custom itinerary based on your interests.
Sintra is Portugal’s fairytale escape—where misty forests, whimsical palaces, and centuries of history collide in a dreamlike setting. Just 40 minutes from Lisbon, this UNESCO World Heritage town has enchanted poets, royals, and romantics for generations.
🏰 A Storybook Past
Sintra’s roots stretch back to prehistoric times, but it flourished under Moorish rule, who built the Castelo dos Mouros (Moorish Castle) in the 8th century. After the Christian reconquest, Sintra became a royal retreat, especially during the 18th and 19th centuries when Romanticism swept through Europe. Artists and aristocrats transformed the town into a canvas of exotic architecture and lush gardens.
📍 Must-See Attractions
Palácio da Pena: A riot of colors and styles perched atop a mountain. This Romantic palace looks like it leapt from a fantasy novel.
Quinta da Regaleira: A mystical estate with secret tunnels, spiral wells, and symbolism tied to alchemy and the Knights Templar.
Castelo dos Mouros: Crumbling stone walls with panoramic views, echoing the days of Moorish rule.
Palácio Nacional de Sintra: Known for its twin conical chimneys and lavish interiors, this was a favorite of Portuguese royalty.
Palácio de Monserrate: A blend of Gothic, Moorish, and Indian influences, surrounded by exotic gardens.
Convento dos Capuchos: A humble 16th-century monastery carved into the rock, offering a stark contrast to Sintra’s opulence.
Cabo da Roca: The westernmost point of mainland Europe, with dramatic cliffs and ocean views.
🌿 Beyond the Palaces
Sintra’s magic isn’t just in its monuments. Wander the Parque da Liberdade, hike the Caminho de Santa Maria, or sample queijadas (sweet cheese tarts) from a local bakery. Even the Sintra Tram, a vintage ride to the coast, feels like a step back in time.
Cascais is Portugal’s coastal jewel—once a sleepy fishing village, now a stylish seaside retreat that still holds onto its charm. In the late 19th century, it became the summer playground of Portuguese royalty, and that aristocratic elegance still lingers in its mansions, gardens, and promenades.
🌊 A Glimpse into Cascais’ Story
Cascais gained prominence when King Luís I chose it as his summer residence in the 1870s. The nobility followed, transforming the town with lavish villas and cultural institutions. During World War II, it became a haven for exiled royals and spies, adding a layer of intrigue to its sun-soaked streets.
📍 Top Places to Visit in Cascais
Museu Condes de Castro Guimarães: A whimsical palace-turned-museum filled with art, Indo-Portuguese furniture, and a 25,000-volume library.
Praia da Rainha: Once Queen Amélia’s private beach, now a picturesque cove perfect for sunbathing and Instagram shots.
Praia do Guincho: A wild, windswept beach ideal for surfing and featured in a James Bond film.
Old Town Cascais: Wander cobbled streets lined with boutiques, cafés, and calçada portuguesa mosaics.
Parque Marechal Carmona: A peaceful park with peacocks, ponds, and picnic spots.
Casa das Histórias Paula Rego: A striking museum dedicated to one of Portugal’s most acclaimed contemporary artists.
Boca do Inferno: A dramatic seaside cliff formation where waves crash into a chasm—especially thrilling during storms.
Cascais is also a gateway to the Sintra-Cascais Natural Park, offering hiking, cycling, and breathtaking coastal views. Whether you're sipping wine by the marina or catching Atlantic breezes on a cliffside trail, Cascais is where elegance meets adventure.
