Lisbon in 5 Days: The Ultimate Guide to History, Fado & Hidden Gems

Fresh off your transatlantic flight, ditch your bags and hop on a tuk tuk tour recommended by your concierge! It's the perfect way to kickstart your Lisbon adventure and conquer Alfama's charming yet hilly streets. Alfama is Lisbon's oldest district, known for its narrow streets, historical charm and Fado houses. Start above the district at the Moorish castle (São Jorge Castle) offering stunning, panoramic views. Make sure you don’t miss the peacocks in the Castle. Next, explore Lisbon's oldest church, the Sé Cathedral, and the National Pantheon, final resting place for Portuguese heroes. Learn about Fado, the melancholic and soulful music genre originating in Lisbon, Portugal, in the early 1820s, at the Fado Museum. Soak up cityscapes from Alfama's miradouros (viewpoints), then get lost in the maze of streets, admiring street art and traditional houses. In the evenings, Alfama comes alive with Fado performances, a must see while you are there. Tasca do Chico is a great traditional bar with regular Fado singers. Take note of all the Calçada Portuguesa (Portuguese Pavement) mosaics around the city. Following the devastating 1755 earthquake that destroyed much of Lisbon, the city needed a practical and readily available solution for rebuilding its streets. Calçada Portuguesa emerged as a clever way to utilize the shattered remnants of limestone and basalt buildings. Workers meticulously arranged these fragments to create a sturdy and visually appealing pavement.

Explore Lisbon's maritime history with a morning visit to the UNESCO-listed Torre de Belém a magnificent watchtower offering stunning Tagus River views. Next door, explore the architectural wonder of the Mosteiro dos Jerónimos, another UNESCO gem known for its intricate Manueline style and tombs of Portuguese icons like Vasco da Gama. Refuel with a legendary Pastéis de Belém, a delicious custard tart, before a scenic afternoon stroll along the Tagus River. If time allows, visit the Padrão dos Descobrimentos monument, a tribute to Portugal's Age of Discovery or take a scenic boat ride.

Immerse yourself in the historic charm of Sintra on this whirlwind day trip! Ascend to the Pena National Palace, a kaleidoscope of colors boasting captivating towers and breathtaking panoramic views. Don't miss getting lost in the whimsical Pena Park gardens, where exotic flora and hidden grottos create a fairy tale atmosphere. Next, explore the mysteries of Quinta da Regaleira, the 19th-century estate located that is also a UNESCO World Heritage Site. Savor a delicious Portuguese lunch then journey west to Cabo da Roca, continental Europe's westernmost point. Cascais, your next stop, offers a delightful change of pace. Stroll along the harbor, a vibrant scene of bobbing boats and fresh seafood stalls. Relax on the beach, or delve into history at the imposing Cidadela de Cascais fortress, a reminder of Portugal's rich maritime past. Make sure to get a treat at one of the artisan gelato’s before heading back to Lisbon.

Lisbon's iconic Tram 28 whisks you through vibrant neighborhoods. Start chic in Chiado with elegant shops, Brasileira cafes and the São Carlos National Theatre. Dive into history and buzz at Baixa's Praça do Comércio, Time Out Market and the Santa Justa Lift. Ascend to Alfama for its soul - get lost in the street and soak in city views. Graça offers peace with panoramic views, the Igreja e Convento da Graça and Jardim da Graça. Finally, Estrela exudes elegance with the magnificent Basílica da Estrela, Jardim da Estrela park and the Estrela Cemetery. Tram 28 is your Lisbon on rails adventure - enjoy the ride and explore each neighborhood's unique charm! Note... Tram 28 can be quite crowded during peak seasons. Tram 12 also follows a similar route; this route can also be done by tuk tuk as well as a walking route (albeit challenging with the hills). End the day with a delicious dinner at one of the rooftop bars and restaurants. Seen Lisboa at Tivoli Avenida Liberdad is a great option.

Embark on a charming Lisbon stroll! Start grand at Praça do Comércio, marveling at the arch and soaking up the lively atmosphere. Wander down Rua Augusta, a pedestrian haven for shopping and people-watching. Next, Praça Figueira awaits with its flower stalls and vibrant energy - grab a drink and observe the city unfold. Ascend the Rua Augusta Arch for panoramic city views, then descend to Cais da Ribeira (literally meaning "Docks of the Riverside"), the historic waterfront. Finally, end your afternoon with a drink by the water, watching the sunset paint the sky as you sip a local vinho verde.