Portugal's compact geography makes a 10-day trip feel generous. Four nights in Lisbon cover the city and a Sintra day trip; three nights in Porto do the Ribeira and its port houses; three nights in a Douro Valley quinta finish with wine, the river, and the single prettiest train ride in Iberia. No hire car needed — Lisbon–Porto is 2h 40m by train, Porto–Pinhão is 2h 30m along the river.
Each day is written to balance structure with breathing room. Named hotels, named meals, named activities; logistics noted where they matter.
Land at LIS, 15-minute taxi to your hotel in Baixa or Alfama. Afternoon walk through Alfama's medieval lanes, sunset at the Miradouro da Senhora do Monte, and a first-night fado dinner at Clube de Fado or Tasca do Chico.
Morning tram 15 to Belém — Jerónimos Monastery, Pastéis de Belém for lunch (the original tart recipe, on-site since 1837), Belém Tower. Afternoon back in the centre: Praça do Comércio, the Santa Justa lift, Chiado shopping. Dinner at Taberna da Rua das Flores or Cervejaria Ramiro.
Train from Rossio to Sintra (40 min, €2.30). Morning at Pena Palace (queue early). Lunch at Piriquita (the local travesseiros pastry). Afternoon at Quinta da Regaleira's initiation well and gardens. Back to Lisbon by 18:00 for a Bairro Alto evening.
Morning at LX Factory — creative-industrial complex with bookshops (Ler Devagar), independent design stores, and cafés. Lunch at Time Out Market Lisboa. Afternoon at the Gulbenkian Museum (Calouste Gulbenkian's private collection, one of Europe's best). Last-night dinner at Taberna do Mercado or Belcanto (2-Michelin star).
Alfa Pendular train Lisbon Oriente to Porto Campanhã (2h 40m, €30). Check into your Porto hotel by lunch. Afternoon walking Porto's Ribeira (UNESCO waterfront), Livraria Lello (the inspiration for Harry Potter's Flourish & Blotts), São Bento station's azulejo panels.
Morning crossing the Dom Luís I bridge to Vila Nova de Gaia for port-house tours — Taylor's, Graham's, and Sandeman are the big names, Cálem is the easiest first-visit. Lunch at DOP or The Yeatman's restaurant. Afternoon at the Serralves Foundation (contemporary art + Art Deco villa).
The single most scenic train ride in Iberia: Porto São Bento to Pinhão, 2h 30m along the Douro River through terraced vineyards. Check into a valley quinta, wine tasting at the property, and dinner overlooking the river.
Full day in the Douro. Morning tour of a working quinta (Quinta do Noval, Quinta do Crasto, or Quinta Nova) with barrel tasting. Lunch at a vineyard-restaurant. Afternoon on the river — rabelo boat or kayak. Evening at Six Senses' tasting room or back at your property.
A quieter last valley day — drive (or cab) to Amarante (medieval Portuguese town with the Ponte de São Gonçalo bridge) or Lamego (12th-century fortress + vineyard hills). Back to your quinta for a final valley sunset.
Morning train back to Porto (2h 30m). Lunch in the Ribeira. Taxi to OPO airport. Most EU connections are direct from Porto; US connections usually via Lisbon or Madrid.
For Lisbon, Porto, and the Douro Valley, yes — it's the canonical 'Portugal highlights' trip. Adding the Alentejo (south, slower), the Algarve (coast), or the Azores needs another week each.
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