Day 1: Lisbon Arrival & Alfama Wandering

Arrive in Lisbon, check into your Alfama accommodation. Walk to the Miradouro de Santa Luzia for your first view over the Tagus. Explore Alfama’s alleys — no map, just wander. Visit the castle hill (Castelo de São Jorge, €15 or just walk the free perimeter).

Take Tram 28 through Graça and Baixa. Explore Chiado and the elegant streets around it. For your first evening, book a fado dinner at a small tasca in Alfama — Tasca do Chico (no cover) for an authentic, unpolished experience.

Accommodation: Lisbon Alfama (€35-80/night).

Day 2: Belém & Lisbon’s Monumental Side

Drive or Tram 15 to Belém. Visit the Jerónimos Monastery (€10) and the Torre de Belém. Eat warm pastéis de nata at Pastéis de Belém. Walk along the riverfront to the Padrão dos Descobrimentos.

Explore the Baixa district — Rossio Square, Rua Augusta Arch, and the Elevador de Santa Justa. Visit the Mercado da Ribeira for a final Lisbon feast. Start packing — tomorrow you head into the interior.

Entry: Jerónimos Monastery (€10), Torre de Belém (€8).

Day 3: Évora — Roman Temple, Bones & Alentejo Wine

Drive east from Lisbon to Évora (1.5 hours). Stop at the Baixa da Banheira viewpoint over the cork oak plains — the Montado landscape is Portugal’s most iconic rural scene. Arrive in Évora, a UNESCO World Heritage city, and check into a guesthouse inside the medieval walls.

Visit the Templo de Évora (Roman Temple) — the best-preserved Roman monument in Portugal. Walk through the whitewashed streets to the Capela dos Ossos (Chapel of Bones, €5) in the Church of São Francisco, where the walls are lined with the bones of 5,000 monks. Visit the Évora Cathedral for rooftop views. For dinner, taste Alentejo wine at a local adega and order the region’s signature bread-and-coriander soup (açorda) or black pork (porco preto).

Transport: Car rental (€25-40/day).

Accommodation: Évora city centre (€40-80/night).

Day 4: Alentejo Wine & the Cork Oak Plains

Drive 30 minutes west of Évora to Herdade do Esporão, one of Portugal’s most beautiful wine estates. Take the tour (€15-25) through the vineyards, olive groves, and 14th-century tower. The tasting features their famous Alentejo reds — the Reserva and Monte Velho are exceptional value.

Continue to Monsaraz (45 min east), a hilltop medieval village where the whitewashed houses and castle walls overlook the Alqueva Dam. Walk the castle ramparts, visit a cork workshop (the region produces 50% of the world’s cork), and watch the sunset over the largest artificial lake in Europe. The Alqueva Dark Sky Reserve offers incredible stargazing.

Accommodation: Monsaraz guesthouse or quinta stay (€45-90/night).

Day 5: White Villages — Marvão, Castelo de Vide & the Alentejo Interior

Drive north from Monsaraz to Castelo de Vide (1.5 hours). This hilltop town is famous for its whitewashed streets, a medieval castle, and the Fonte da Vila — a stunning 16th-century fountain where spring water flows freely. Walk the Judiaria (Jewish quarter) with its distinctive dark slate houses.

Continue 15 minutes to Marvão, arguably Portugal’s most beautiful hilltop village. Perched on a sheer granite ridge at 860 metres, it offers views across the Alentejo plains all the way to Spain. Walk the castle walls, have coffee on the main square, and just soak in the silence. The drive between these two villages along the N359 is stunning. Overnight in Marvão.

Transport: Car rental.

Accommodation: Marvão pousada or guesthouse (€50-100/night).

Day 6: Coimbra — Portugal’s Student Heart

Drive north from Marvão to Coimbra (2.5 hours). Park outside the old town and walk up through the narrow medieval streets to the University of Coimbra, one of the oldest in Europe (founded 1290). Visit the Joanine Library (Biblioteca Joanina, €12) — a breathtaking baroque library with carved gilded wood, exotic woods, and a resident bat colony that eats book-damaging insects.

Visit the Cathedral of Coimbra (Sé Velha) — the Romanesque old cathedral. Explore the narrow alleys of the Alta district and the riverside Baixa. Coimbra has its own style of fado (Coimbra fado), traditionally sung by male university students. For dinner, eat at a riverside restaurant watching the Mondego River flow under the Santa Clara Bridge.

Transport: Car rental.

Accommodation: Coimbra city centre (€35-70/night).

Day 7: Cruise to Porto — Train Through the Douro Valley

Drop your rental car in Coimbra and catch the train to Porto (1.5 hours, €15-25). Check into your Porto accommodation in the Ribeira or near Aliados. Spend the afternoon crossing the Dom Luís I Bridge to Vila Nova de Gaia for Port wine tastings at Taylor’s or Graham’s (€15-25). Walk the Gaia riverfront at sunset.

Dinner in the Ribeira district — order a Francesinha at a local tasca or grilled fish at a riverside restaurant. Watch the lights come on across the Douro from a pavement cafe in Cais da Ribeira.

Transport: Train Coimbra-Porto (€15-25). Car drop-off in Porto.

Accommodation: Porto Ribeira (€40-90/night).

Day 8: Porto’s Treasures

Pre-book Livraria Lello (€8, 9 AM entry) for the magnificent staircase. Climb the Clérigos Tower (€8) for the best views over the city. Admire the azulejos at São Bento station.

Visit the Serralves Museum (€12-20) or simply wander through the Mercado do Bolhão for last souvenirs. Head up to Jardins do Palácio de Cristal for peacocks and stunning river views. For your last night in Porto, book a table at a traditional porto restaurant and order a bottle of Douro DOC wine.

Entry: Livraria Lello (€8), Clérigos Tower (€8), Serralves (€12-20).

Day 9: Douro Valley Day Trip — Pinhão & the Vineyards

Take the early train (8:30 AM) from São Bento to Pinhão (2 hours, sit right side). Visit the azulejo-covered Pinhão station, then walk to Quinta do Crasto or take a taxi from Pinhão for a tour and tasting (€15). The terrace at Crasto with its famous infinity-pool view is the quintessential Douro photo.

Take a sunset rabelo boat trip from Pinhão (1 hour, €15) or walk through the riverside vineyards back to town. Catch the 5 PM train back to Porto (arriving 7 PM). For your final dinner, book a tasting menu at DOP or Antiqvvm for a memorable farewell.

Transport: Train Porto-Pinhão (€10 each way).

Day 10: Porto Final Morning & Departure

One last morning in Porto. Walk the Ribeira one final time, buy Port wine at the Mercado do Bolhão for gifts, and grab a pastel de nata from Manteigaria Porto. If your flight isn’t until the evening, cross to Gaia and visit one more Port wine lodge you missed — Sandeman or Taylor’s cellars are worth it.

The Porto metro from Trindade station reaches the airport in 35 minutes (€2.50). The Porto airport (OPO) is efficient — arrive 1.5-2 hours before for European flights, 2.5 hours for international departures.