Adventurous 5-Day Trip to Lisbon and Surroundings Itinerary

Begin your day with a visit to the imposing St. George's Castle (Castelo de São Jorge), where you can explore the ancient fortifications and enjoy stunning views of the city. For breakfast, grab a coffee and a treat at Time Out Market Lisboa, a foodie paradise.

After the castle, take a trip to the charming district of Alfama, known for its narrow streets and traditional Fado music. Have a traditional Portuguese lunch at Taberna da Rua das Flores and then relax at the serene Miradouro da Senhora do Monte (Miradouro de Nossa Senhora do Monte), one of the city's best viewpoints.

Dine at Belcanto, a two-Michelin-star restaurant offering a sophisticated take on Portuguese cuisine. Afterward, take a leisurely stroll through the beautifully lit streets of Alfama.

Enjoy a scenic drive to the coastal town of Cascais. Start your day with a delicious breakfast at Landeau Chocolate, known for its exquisite chocolate creations. Afterward, take a leisurely walk along the Cascais Marina (Marina de Cascais) and explore the charming streets of the town.

Have a delightful seafood lunch at Solar dos Presuntos, a restaurant with a long-standing reputation for quality cuisine. Post-lunch, visit the fascinating Casa das Histórias Paula Rego, a museum dedicated to the works of the renowned Portuguese artist.

As the sun sets, relax at Guincho Beach (Praia do Guincho), known for its windswept beauty. Enjoy a dinner with a view at Fortaleza do Guincho, a Michelin-starred restaurant located in a historic fortress.

Embark on a day trip to Sintra, where you'll be greeted by the fairytale architecture of the Pena National Palace (Palácio Nacional da Pena). Start your day with a hearty breakfast at A Cevicheria, known for its creative dishes and vibrant atmosphere.

Explore the mystical Monserrate Palace (Palácio de Monserrate) and its lush gardens. For lunch, enjoy the gastronomic offerings at 5 Oceanos, a restaurant that specializes in fresh seafood. Afterward, take a moment to appreciate the westernmost point of continental Europe at Cabo da Roca.

Return to Lisbon and cap off your day with a visit to the elegant Parque das Nações (Nations Park), where you can enjoy a leisurely evening stroll. Dine at Sea Me - Peixaria Moderna, a top spot for seafood lovers, and reflect on the day's adventures.

Discover the lesser-known side of Lisbon with a visit to the quirky LX Factory, a hub of creativity and innovation. Enjoy a casual breakfast at The Decadente Restaurante & Bar, located in the bohemian Bairro Alto district.

After exploring LX Factory, take a short drive to the picturesque town of Óbidos, known for its well-preserved medieval architecture. Enjoy a traditional Portuguese lunch at Petiscaria Ideal, and take some time to walk the charming cobblestone streets.

Return to Lisbon and spend your final evening at Park Bar, a rooftop bar with panoramic views of the city. Toast to your adventurous trip with a drink as you reminisce about the highlights. For dinner, indulge in the flavors of 100 Maneiras Bistro (Bistro 100 Maneiras), a restaurant known for its bold and creative dishes.