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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 Landmarks and Culinary Delights

Morning
Begin your Lisbon adventure with a traditional Portuguese breakfast at Pasteis de Belem, famous for its custard tarts. Afterward, take a stroll through the historic Belém District (Ajuda, Belém, Restelo, Belem), visiting iconic sites such as the Belém Tower (Torre de Belém) and the grand Monastery of St. Jerome (Mosteiro dos Jeronimos).
Afternoon
For lunch, savor contemporary Portuguese cuisine at 100 Maneiras. Post lunch, explore the vibrant Commerce Square (Praça do Comércio), and then take a ride on the iconic 25th of April Bridge (Ponte 25 de Abril) for stunning views of the city.
Evening
As the sun sets, enjoy a sophisticated dining experience at Eleven Restaurant, offering panoramic views of the city. End your evening with a leisurely walk through the historic neighborhood of Alfama, known for its Fado music and winding streets.
Bedtime
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Avenida da Liberdade

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Monastery of St. Jerome (Mosteiro dos Jeronimos)

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Commerce Square (Praça do Comércio)

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25th of April Bridge (Ponte 25 de Abril)

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Alfama

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City Exploration and Fado Serenade

Morning
Kick off the day with a guided Lisbon City Walking Tour with Food Tasting and Drinks. Sample local delicacies and learn about the city's history. The tour should take you through the heart of the city, including the vibrant neighborhoods of Bairro Alto and Chiado.
Afternoon
For lunch, head to Taberna da Rua das Flores for a taste of authentic Portuguese cuisine. Post lunch, visit the National Pantheon of Santa Engracia (Panteao Nacional) and enjoy the panoramic views from the top.
Evening
Experience the soul-stirring sounds of Fado at an intimate live music show at Lisbon Evening Intimate Live Fado Music Show with Port wine. Pair the music with a glass of Port wine for a truly memorable evening.
Bedtime
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Lisbon City Walking Tour with Food Tastings and Drinks

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National Pantheon of Santa Engracia (Santa Egracia Panteao Nacional Lisbon)

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Lisbon Evening Intimate Live Fado Music Show with Port wine

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Enchanting Palaces and Scenic Views

Morning
Take a day trip to the magical town of Sintra. Explore the colorful Pena National Palace (Palacio Nacional da Pena) and the mystical Castle of the Moors (Castelo dos Mouros). Enjoy a delightful breakfast at Mini Bar Teatro before embarking on your palace adventure.
Afternoon
Have a leisurely lunch at Tavares Rico, one of Sintra's hidden gems. After lunch, visit the serene Regaleira and the opulent Sintra National Palace (Palácio Nacional de Sintra).
Evening
Conclude your Sintra journey with a visit to the westernmost point of Europe, Cabo da Roca, and witness a breathtaking sunset over the Atlantic Ocean. Enjoy a sumptuous dinner at Feitoria Restaurant & Wine Bar in Cascais, reflecting on the day's magical experiences.
Bedtime
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Pena National Palace (Palacio Nacional da Pena)

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Castle of the Moors (Castelo dos Mouros)

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Sintra

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Sintra National Palace (Palácio Nacional de Sintra)

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Cabo da Roca

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Coastal Wonders and Sunset Soiree

Morning
Start your day with a hearty breakfast at Solar dos Presuntos, then explore the charming seaside town of Cascais. Visit the Cascais Marina (Marina de Cascais) and the Cascais Beach (Praia de Cascais) for a relaxing morning by the sea.
Afternoon
Enjoy a delightful lunch at Bairro do Avillez, followed by a visit to the intriguing Lighthouse Museum (Museu de Santa Marta). Take a leisurely walk along the Cascais Promenade (Paredao de Cascais) and soak in the coastal views.
Evening
Embark on a Lisbon Sunset Boat Party Cruise with DJ and Open Bar for a lively and memorable evening. Dance to the music, enjoy the open bar, and witness the stunning sunset over the waters. Return to Lisbon for a late dinner at Time Out Market Lisboa, where you can indulge in a variety of culinary delights.
Bedtime
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São Vicente de Fora Monastery

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Ajuda National Palace (Palacio Nacional Ajuda)

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Bloukrans Bridge

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Cultural Heritage and Modern Marvels

Morning
Begin with a visit to the historic Lisbon Cathedral (Sé de Lisboa), then explore the ancient Castelo de Sao Jorge (St. George's Castle) for panoramic views of the city. Enjoy a traditional Portuguese breakfast at Pasteis de Belem before you head out.
Afternoon
For lunch, try the innovative dishes at Mini Bar Teatro, and then visit the futuristic Oceanarium Of Lisbon (Oceanário de Lisboa) in the Parque das Nações area. Take a relaxed stroll around the area and admire the modern architecture.
Evening
Conclude your Lisbon journey with a gastronomic experience at Belcanto, one of the city's finest restaurants. After dinner, take a Daytime/Sunset/Night City Sailboat Tour with Drinks to see the city from a different perspective, with the lights of the city reflecting on the gentle waters.
Bedtime
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Lisbon Cathedral (Sé de Lisboa)

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Castelo de Sao Jorge (St. George's Castle)

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Adjacent Cities

SintraCascaisÉvoraCoimbraGuimarãesBragaPorto

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