Lisbon Highlights in 5 Days Itinerary

Begin your second day with a visit to the impressive Monastery of St. Jerome (Mosteiro dos Jeronimos). This UNESCO World Heritage site is an architectural masterpiece and provides insight into Portugal's rich history. After exploring the monastery, enjoy breakfast at Pasteis de Belem, where you can savor their famous custard tarts.

Next, make your way to the bustling Ribeira Market (Mercado da Ribeira). This market offers a wide variety of local produce, food stalls, and artisanal products. It's an excellent place to sample some traditional Portuguese dishes for lunch. Afterward, take some time to explore the nearby Lisbon Cathedral (Sé de Lisboa), one of the city's oldest buildings.

In the evening, enjoy a scenic view from Miradouro Sao Pedro de Alcantara, one of Lisbon's best viewpoints. As you watch the sunset over the city, consider having dinner at The Decadente, which offers contemporary Portuguese cuisine with an amazing view.

Begin your fourth day with a visit to the Belém Tower (Torre de Belém). This iconic fortress is a UNESCO World Heritage site and offers stunning views of the Tagus River. After exploring the tower, head to Café do Forte for breakfast, where you can enjoy delicious pastries and coffee with a view of the river.

In the afternoon, make your way to the National Museum of Ancient Art (NMAA). This museum houses an impressive collection of Portuguese art from the Middle Ages to the 19th century. For lunch, try A Cevicheria, known for its modern take on traditional Portuguese dishes. After lunch, take a leisurely stroll through the beautiful Águas Livres Aqueduct, an engineering marvel that once supplied water to Lisbon.

End your day with a visit to the vibrant Chiado district. This area is known for its lively atmosphere, trendy shops, and historic cafes. Enjoy dinner at Bairro do Avillez, which offers contemporary Portuguese cuisine in a stylish setting. After dinner, consider catching a live Fado performance at one of Chiado's famous Fado houses.

Miradouro da Senhora do Monte (Miradouro de Nossa Senhora do Monte) is one of Lisbon's highest viewpoints and offers panoramic views over the city. Start your day here to capture some breathtaking photos. For breakfast, head to Fabrica Coffee Roasters, known for its excellent coffee and pastries.

Castelo de Sao Jorge (St. George's Castle) is next on your list. This historic castle provides not only a deep dive into Lisbon's history but also some of the best views over Alfama and beyond. For lunch nearby, try Chapitô à Mesa, which offers delicious food with an incredible view over Lisbon.

Lisbon Booze Cruise with Live DJ and Open Bar is perfect for wrapping up your trip in style! Enjoy an evening cruise along the Tagus River with live music and drinks as you watch Lisbon light up at night from water level! Before boarding this fun cruise experience have dinner at Time Out Market Lisboa where you can choose from various food stalls offering diverse cuisines.

Start your third day with an exciting adventure: From Lisbon Sintra-Cascais Natural Park Rock Climbing Tour. This tour will take you through some of Portugal's most beautiful natural landscapes while offering an adrenaline-pumping rock climbing experience. Have breakfast before you leave at Nicolau Lisboa for some healthy options.

After your morning adventure, continue exploring Sintra by visiting the magnificent Pena Palace and Park. The colorful palace looks like something out of a fairy tale and provides breathtaking views over Sintra and beyond. For lunch in Sintra, try out Tulhas, known for its traditional Portuguese dishes.

Conclude your day trip by heading towards Cascais along the scenic coastal route Cabo da Roca – Europe’s westernmost point! Enjoy strolling around this charming seaside town before having dinner at Cascais' popular restaurant:  Mar do Inferno known for its fresh seafood delicacies.