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Ultimate 5-Day Lisbon Adventure with Sintra and Cascais

Ultimate 5-Day Lisbon Adventure with Sintra and Cascais Itinerary

Last updated: 2024 Jun 14

Historic Lisbon and Alfama Exploration

Morning
Begin your Lisbon adventure with a traditional Portuguese breakfast at Pasteis de Belem, known for its iconic custard tarts. Afterward, take a Lisbon History, Stories and Lifestyle Walking Tour to immerse yourself in the city's vibrant history and culture. Visit landmarks such as the Commerce Square (Praça do Comércio) and the Lisbon Cathedral (Sé de Lisboa).
Afternoon
For lunch, savor contemporary Portuguese cuisine at 100 Maneiras. Spend your afternoon exploring the ancient Alfama district, wandering through its narrow streets and alleys. Visit the Castelo de Sao Jorge (St. George's Castle) for panoramic views of the city and the Tagus River.
Evening
As the sun sets, enjoy a memorable dining experience at Eleven Restaurant, offering innovative dishes in an elegant setting. Conclude your evening with the Lisbon 3-Hour Sightseeing Tour by Tuk Tuk, allowing you to discover the city's hidden gems and stunning viewpoints.
Bedtime
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Lisbon History, Stories and Lifestyle Walking Tour

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Commerce Square (Praça do Comércio)

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Monuments and Modernity

Morning
Start with a visit to the iconic Belém Tower (Torre de Belém), a symbol of the Age of Discovery. Enjoy a light breakfast at the nearby Time Out Market Lisboa, offering a variety of culinary delights. Continue to the Monument to the Discoveries (Padrão dos Descobrimentos) and the Monastery of St. Jerome (Mosteiro dos Jeronimos).
Afternoon
Have lunch at Cervejaria Ramiro, a renowned seafood restaurant. Afterward, take a leisurely stroll along the waterfront and visit the 25th of April Bridge (Ponte 25 de Abril), often compared to the Golden Gate Bridge. Explore the contemporary architecture of the National Sanctuary of Christ the King (Cristo Rei).
Evening
Dine at A Cevicheria, known for its creative ceviche dishes and vibrant atmosphere. Cap off the evening with a visit to the Miradouro da Senhora do Monte (Miradouro de Nossa Senhora do Monte), one of Lisbon's most stunning viewpoints, offering panoramic views of the city.
Bedtime
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Belém Tower (Torre de Belém)

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Monument to the Discoveries (Padrão dos Descobrimentos)

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Enchanting Sintra and Pena Palace

Morning
Embark on a magical journey with the Lisbon Guided Day Tour of Sintra, Pena, Regaleira & Cascais. Explore the mystical Regaleira and the colorful Pena National Palace (Palacio Nacional da Pena). Take in the breathtaking views of the surrounding landscape.
Afternoon
Enjoy a delightful lunch at Taberna da Rua das Flores, a charming eatery serving traditional Portuguese dishes. Afterward, take a leisurely walk through the Sintra town, visiting the quaint shops and cafes.
Evening
Return to Lisbon and indulge in a sumptuous dinner at Mini Bar Teatro, known for its theatrical presentation of dishes. For a relaxing end to the day, enjoy the Lisbon Oceanarium Of Lisbon Entrance Ticket, one of the largest aquariums in the world, housing a diverse range of marine life.
Bedtime
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Regaleira

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Charming Cascais and Sunset Cruise

Morning
Begin your day with a visit to the Estoril, known for its beautiful beaches and the famous Estoril Casino. Enjoy a delightful breakfast at a local cafe. Explore the town before heading to Cabo da Roca, the westernmost point of continental Europe.
Afternoon
Have lunch at Tavares Rico, one of the oldest and most prestigious restaurants in Portugal. Spend your afternoon leisurely in Cascais, visiting the Castle of the Moors (Castelo dos Mouros) and the Sintra National Palace (Palácio Nacional de Sintra) if you missed them on the Sintra tour.
Evening
Conclude your day with the highlight, the Lisbon Sunset Boat Party Cruise with DJ and Open Bar. Dance to the music, enjoy the open bar, and witness a breathtaking sunset over the waters, creating memories that will last a lifetime.
Bedtime
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Estoril

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Cabo da Roca

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Cultural Delights and Fado Finale

Morning
Start with a visit to the National Pantheon of Santa Engracia (Santa Egracia Panteao Nacional Lisbon), a stunning example of baroque architecture. Enjoy a traditional Portuguese breakfast at Cantinho do Avillez, known for its cozy ambiance and delectable pastries.
Afternoon
For lunch, head to Belcanto, a two-Michelin-star restaurant offering a sophisticated take on Portuguese cuisine. Spend your afternoon exploring the vibrant neighborhood of Bairro do Avillez, visiting its shops and galleries.
Evening
Conclude your Lisbon journey with the soul-stirring Lisbon Evening Intimate Live Fado Music Show with Port wine. Experience the heartfelt melodies of Fado, Portugal's traditional music, while enjoying a glass of Port wine, a perfect end to a memorable trip.
Bedtime
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