Arrive in Lisbon and settle into your accommodation in or near Baixa/Alfama; drop your bags, grab an espresso at a local pastelaria like Pastelaria Santo António, and take a slow stroll down Rua Augusta to orient yourself with the Praça do Comércio waterfront. From there, wander into the narrow lanes of Alfama, pop into the Sé de Lisboa (Lisbon Cathedral) for a quick look at its Romanesque nave, and pause at Miradouro de Santa Luzia for sweeping views of terracotta roofs and the Tagus River.
After lunch at a traditional tasca — try petiscos and a glass of vinho verde at Pois Café or Tasca do Jaime — continue exploring Alfama with a visit to the Museu do Fado to learn about Portugal’s soulful music. Walk up toward São Jorge Castle, enjoy the castle terraces and gardens, and linger at the castle walls as the light softens to get a preview of the city scenes you'll explore in more depth on later days.
As dusk falls, reserve a table at a nearby casa de fado such as Clube de Fado or A Baiuca for an intimate dinner accompanied by live Fado performances, or choose a rooftop bar like Park for cocktails with panoramic views if you prefer a modern vibe. Finish the night with a gentle riverside stroll along Cais do Sodré, soaking in the glow of Lisbon’s hills and preparing for a full day of Belém monuments tomorrow.
Take the tram or a short taxi ride to Belém and begin at the iconic Jerónimos Monastery — wander through its ornate Manueline cloisters and step inside the church where explorers are commemorated. From there, stroll along the riverside to the Torre de Belém and the Monument to the Discoveries, pausing for photos with the Tagus as your backdrop before indulging in a mid-morning treat at Pastéis de Belém, savoring the famous custard tarts still warm from the oven.
After lunch at the shaded terraces of À Margem or the nearby Confeitaria Nacional, visit the Museu Nacional de Arte Antiga or the MAAT for a contrast of old and contemporary Portuguese art and architecture; the MAAT’s rooftop offers striking river views. Continue your relaxed exploration with a walk through the Belém Cultural Center gardens and pop into the Berardo Collection if modern and contemporary works catch your eye, then rest with a coffee at the riverfront cafés while watching sailboats drift by.
Return toward central Lisbon as the sun lowers and stop for a sunset drink at the riverside Kiosk or Espelho d’Água at Praça do Império, taking in the golden light on the monastery façade. For dinner, choose a seafood-focused restaurant such as 43 and try grilled sardines or bacalhau, then consider a gentle evening tram ride back through the city’s lit hills to your Alfama or Baixa base, reflecting on a day that blends maritime history with Lisbon’s café culture.
Catch an early train from Rossio to Sintra and head straight to the Pena Palace to beat the crowds; wander through its fairytale terraces, brightly painted facades and the surrounding Pena Park’s winding trails for spectacular coastal and forest views. Pause for a mid-morning coffee and a travesseiro at Casa Piriquita in the town center before strolling up to the Moorish Castle ramparts to take in panoramic vistas over Sintra’s palaces and the Atlantic beyond.
After a leisurely lunch at Tascantiga or Cantinho Gourmet, descend into the mystical Quinta da Regaleira to explore its grottoes, Initiation Well and secret gardens — let the symbolic architecture and shaded paths unfold at your own pace. If time allows, stop by the elegant Monserrate Palace and gardens for a quieter, botanical contrast to the morning’s spectacle, enjoying the romantic landscaping and exotic plantings.
Return to Lisbon in the late afternoon and freshen up before dinner; choose a relaxed riverside spot in Cais do Sodré or Chiado to compare notes on the day’s sights over fresh seafood or petiscos. If you still have energy, climb to a nearby miradouro such as São Pedro de Alcântara for a night-time panorama of Lisbon’s twinkling hills, closing the day with a gentle reminder of how Sintra’s magic connects to the city you’re exploring.
Set out after breakfast for a scenic drive (or the 30-40 minute train ride from Cais do Sodré) along the Estoril coast to Cascais, pausing at the dramatic cliff-top viewpoint at Boca do Inferno for photos of the waves and sea spray. Once in Cascais, wander the charming old town streets, browse local shops near Largo de Camões, and enjoy a late-morning coffee and a pasteis de nata at Confeitaria Garrett while watching fishermen bring in their catch.
Stroll along the seaside promenade to Praia da Ribeira or Praia do Guincho for relaxed beach time — rent a chair, take a bracing walk on the sand, or if you’re feeling adventurous try kite- or windsurfing at Guincho with a local school. For lunch, choose a waterfront seafood meal at Mar do Inferno or Restaurante Furnas do Guincho, then visit the elegant Palácio dos Condes de Castro Guimarães and its museum and gardens for a peaceful cultural interlude.
As the light softens, enjoy an aperitivo on the Marina’s terraces or at the rooftop of The Albatroz Hotel overlooking the bay, then dine at a cozy tasca such as Casa da Isilda or Taberna Clandestina to sample fresh grilled fish and regional wines. Finish the day with a gentle stroll along the illuminated marina back toward the train station, savoring the coastal calm before returning to Lisbon or settling in Cascais for the night.
Start your final morning with a visit to the Mercado da Ribeira (Time Out Market) for a last taste of Lisbon — sample fresh pastries, local cheeses and a bica while browsing stalls for gourmet souvenirs. Then wander up through Chiado toward the Feira da Ladra in Alfama (if it’s a market day) or explore the antique and craft stalls around Igreja de São Vicente de Fora, picking up a few handcrafted tiles or a bottle of Portuguese olive oil as keepsakes.
After a leisurely lunch of petiscos in Bairro Alto or a riverside meal in Cais do Sodré, climb to Miradouro de São Pedro de Alcântara and then to Miradouro da Senhora do Monte for sweeping afternoon views that knit together the city, the Tagus and the palaces you visited in Sintra. Use this calm, panoramic hour to retrace highlights, take final photos, and return to your accommodation to collect luggage with time to spare for your onward journey.
If your departure allows a final Lisbon evening, enjoy an early dinner near Praça do Comércio with grilled fish or bacalhau and a glass of vinho verde, then take a gentle riverside stroll to the Cais to watch the lights shimmer on the water — a peaceful farewell to the city. If leaving tonight, head to the airport or train station relaxed and nourished by Lisbon’s flavors and views, carrying with you the memories of Alfama’s lanes, Belém’s monuments, Sintra’s palaces and Cascais’s coast.