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Ultimate 5-Day Lisbon, Sintra, and Cascais Adventure

Ultimate 5-Day Lisbon, Sintra, and Cascais Adventure Itinerary

Last updated: 2024 Jun 14

Historic Lisbon and Local Delights

Morning
Start your Lisbon adventure with a guided Lisbon City Walking Tour with Food Tasting and Drinks. Explore the historic Alfama district, visit the Lisbon Cathedral (Sé de Lisboa) , and enjoy traditional Portuguese pastries and coffee at a local cafe.
Afternoon
After the tour, take a short walk to the iconic Commerce Square (Praça do Comércio) and have a delightful lunch at Time Out Market Lisboa, where you can sample a variety of local dishes.
Evening
Experience the vibrant nightlife of Lisbon with an intimate live Fado music show and Port wine at Lisbon Evening Intimate Live Fado Music Show with Port wine. For dinner, indulge in the innovative cuisine of Mini Bar Teatro, known for its creative tapas-style dishes.
Bedtime
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Visit Lisbon City Walking Tour with Food Tastings and Drinks in Lisbon
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Lisbon City Walking Tour with Food Tasting and Drinks

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Visit Commerce Square (Praça do Comércio) in Lisbon
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Commerce Square (Praça do Comércio)

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Lisbon's Landmarks and Breathtaking Views

Morning
Begin your day with a visit to the historic Belém Tower (Torre de Belém) and enjoy the stunning riverside location. For breakfast, savor the famous pastries at Pasteis de Belem.
Afternoon
Explore the grandeur of the Monastery of St. Jerome (Mosteiro dos Jeronimos) and then take a short drive to the 25th of April Bridge (Ponte 25 de Abril) for panoramic views of the city. Have lunch at Cervejaria Ramiro, a renowned seafood restaurant.
Evening
As the sun sets, embark on a Lisbon Sunset Cruise and enjoy the city's landmarks from the water. Conclude the evening with a sophisticated dining experience at Eleven Restaurant, offering a blend of Portuguese and international flavors.
Bedtime
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Belém Tower (Torre de Belém)

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Visit Monastery of St. Jerome (Mosteiro dos Jeronimos) in Lisbon
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Monastery of St. Jerome (Mosteiro dos Jeronimos)

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Majestic Palaces and Enchanting Gardens

Morning
Take a day trip to Sintra and visit the fairytale-like Pena National Palace (Palacio Nacional da Pena). Enjoy the morning exploring the colorful palace and its surrounding park. Have breakfast at the palace's cafe.
Afternoon
After Pena Palace, continue to the mystical Castle of the Moors (Castelo dos Mouros) and immerse yourself in history and breathtaking views. For lunch, dine at Tavares Rico, a Michelin-starred restaurant in the heart of Sintra.
Evening
Conclude your Sintra visit with a serene walk through the gardens of the Quinta da Regaleira E-Ticket & Optional Audio Guide. Return to Lisbon and enjoy a relaxed dinner at Taberna da Rua das Flores, known for its traditional Portuguese cuisine.
Bedtime
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Visit Pena National Palace (Palacio Nacional da Pena) in Sintra, Portugal
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Pena National Palace (Palacio Nacional da Pena)

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Visit Castle of the Moors (Castelo dos Mouros) in Sintra, Portugal
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Castle of the Moors (Castelo dos Mouros)

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Coastal Charms and Scenic Drives

Morning
Start your day with a visit to the westernmost point of continental Europe, Cabo da Roca. Take in the dramatic cliffs and the vast Atlantic Ocean. Have breakfast at a local cafe in the area.
Afternoon
Drive along the stunning coast to Cascais and explore the charming town. Visit the Cascais Marina (Marina de Cascais) and enjoy a leisurely lunch at A Cevicheria, known for its fresh and innovative seafood dishes.
Evening
Relax with a Lisbon Daytime/Sunset/Night City Sailboat Tour with Drinks and witness the beauty of the Lisbon coast from the water. For dinner, head back to Lisbon and dine at 100 Maneiras, a restaurant that offers a unique culinary experience.
Bedtime
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Visit Cabo da Roca in Cascais, Portugal
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Cabo da Roca

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Cascais Marina (Marina de Cascais)

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Culinary Delights and Cultural Gems

Morning
Participate in a Lisbon Gourmet Food and Wine Walking Tour to discover the city's culinary scene. Visit local markets, taste a variety of Portuguese dishes, and learn about the history of Lisbon's gastronomy.
Afternoon
After the tour, take an electric bike ride through the city's hills with the Lisbon 2.5-Hour Hills Tour by Electric Bike. Enjoy the panoramic views and stop for a light lunch at a hidden gem recommended by your guide.
Evening
Conclude your trip with a memorable Lisbon Sunset Boat Party Cruise with DJ and Open Bar. Dance the night away and enjoy the open bar as you take in the stunning views of the Lisbon skyline. For a late-night snack, head to Bairro do Avillez, a lively spot with a variety of dining options.
Bedtime
Find amazing hotels in Lisbon.
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Lisbon Gourmet Food and Wine Walking Tour

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Lisbon 2.5-Hour Hills Tour by Electric Bike

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