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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 hearty breakfast at Time Out Market Lisboa, where you can sample a variety of local delicacies. After breakfast, take a stroll to the iconic Belém Tower (Torre de Belém), a symbol of the Age of Discovery. Continue to the grand Monastery of St. Jerome (Mosteiro dos Jeronimos), a UNESCO World Heritage site, to admire its stunning architecture.
Afternoon
For lunch, indulge in the famous custard tarts at Pasteis de Belem. Post lunch, visit the historic Commerce Square (Praça do Comércio), the largest square in Lisbon, and then explore the ancient Lisbon Cathedral (Sé de Lisboa).
Evening
As the sun sets, enjoy a sophisticated dinner at Feitoria Restaurant & Wine Bar. Conclude your evening with a live Fado in Chiado show, immersing yourself in the soulful sounds of traditional Portuguese music.
Bedtime
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Enchanting Palaces and Scenic Views

Morning
Fuel up for the day with breakfast at Tavares Rico before embarking on your journey. Visit the colorful and whimsical Pena National Palace (Palacio Nacional da Pena), a true fairy-tale castle. Explore the lush gardens and enjoy panoramic views of the surrounding area.
Afternoon
For lunch, take a break at Taberna da Rua das Flores, a charming eatery offering traditional Portuguese dishes. Post lunch, visit the mystical Monserrate Palace, known for its exotic gardens and architectural beauty.
Evening
Return to Lisbon and dine at Mini Bar Teatro, a place that combines creativity and gastronomy. Cap off the evening with a leisurely walk through the historic neighborhood of Alfama, known for its narrow streets and traditional Fado houses.
Bedtime
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Cultural Immersion and Modern Wonders

Morning
Start with a guided Lisbon History and Culture Private or Shared Walking Tour to gain insights into the city's rich heritage. For a quick bite, visit Cervejaria Ramiro for some of the best seafood in town.
Afternoon
Post-tour, visit the contemporary Oceanarium Of Lisbon, one of the largest indoor aquariums in Europe. Later, take a ride on the iconic 25th of April Bridge (Ponte 25 de Abril) for stunning views of the city.
Evening
Enjoy a delightful dinner at Bairro do Avillez, a vibrant spot offering a range of culinary experiences. Conclude your day with a visit to the picturesque Miradouro da Senhora do Monte (Miradouro de Nossa Senhora do Monte) for panoramic views of Lisbon by night.
Bedtime
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Coastal Charms and Historical Marvels

Morning
Begin with breakfast at Solar dos Presuntos, a classic choice for a traditional Portuguese morning meal. Afterward, take a leisurely walk along the Cascais promenade, enjoying the fresh sea breeze and the views of the Atlantic.
Afternoon
For lunch, head to 100 Maneiras and savor their innovative dishes in a stylish setting. Post lunch, visit the Castle of the Moors (Castelo dos Mouros) in Sintra, an impressive hilltop fortress with panoramic views of the region.
Evening
Return to Lisbon and experience the vibrant nightlife on a Lisbon Day, Afternoon, or Sunset Boat Cruise with Wine. Enjoy the open bar and the DJ's tunes as you cruise along the Tagus River, taking in the city's illuminated skyline.
Bedtime
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Final Day of Exploration and Celebration

Morning
Conclude your trip with a visit to the historic Castelo de Sao Jorge (St. George's Castle), where you can enjoy the morning breeze and panoramic views of the city. For breakfast, try the innovative offerings at Eleven Restaurant.
Afternoon
After soaking in the history, take a guided Lisbon Guided Tuk-Tuk Tour with Hotel Pickup to explore the city's hidden gems and vibrant neighborhoods. For a quick bite, stop by Cantinho do Avillez for some contemporary Portuguese cuisine.
Evening
As the sun sets on your trip, enjoy a memorable farewell dinner at Largo do Paço - Casa da Calçada Relais & Châteaux. Reflect on your Lisbon adventure over fine dining and perhaps a glass of local wine. Later, you can choose to relax or continue the celebration with a visit to a recommended bar or lounge for drinks and live music.
Bedtime
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