Two Weeks in Portugal: The Ultimate 14-Day Itinerary

Two weeks in Portugal is close to perfect. You get the cities, the coast, the wine country, the medieval interior, and enough time to sit in a café and simply absorb the light. This itinerary runs south to north, ending in Porto — a great finishing point if you’re flying out from there.

Days 1–3 – Lisbon

Three days in Lisbon covers everything properly. Day one: Alfama, Castelo de São Jorge, Tram 28, and an evening of fado. Day two: Jerónimos Monastery and Belém Tower, then downtown Baixa/Chiado and the Santa Justa Lift. Day three: rooftop bars (the Bairro Alto and LX Factory market on Sundays), the National Tile Museum (Museu do Azulejo), and evening in Mouraria — the old Moorish quarter with excellent cheap tascas (traditional restaurants).

Day 4 – Sintra

Day trip by train from Rossio Station. Pena Palace (book online, arrive early), Quinta da Regaleira (the gothic gardens and initiation wells are extraordinary), and the Moorish Castle. Return via Cascais for a seafood dinner by the harbour.

Days 5–6 – Alentejo

Hire a car and drive east to Évora — a UNESCO World Heritage medieval city with a Roman temple, gothic cathedral, and the remarkable Chapel of Bones. Spend the first night here.

Day six, drive north through the Alentejo plains to Monsaraz — a tiny hilltop village with white walls and battlements overlooking the Alqueva reservoir. Continue to Marvão, arguably Portugal’s most dramatic hilltop fortified village, perched on a rocky promontory at 862m with views into Spain.

Day 7 – Algarve

Drive south to the Algarve coast. The west (around Sagres and Lagos) is wilder, more rugged, and windswept — sea-carved cliffs, hidden coves, and powerful Atlantic surf. The east (Tavira, Faro) is calmer, with long sandy beaches and a more relaxed atmosphere.

Sagres is worth the drive for the moody feel of standing at Europe’s southwest corner. The Ponta de Sagres fortress sits on a flat promontory above sheer cliffs where the Atlantic meets history.

Days 8–9 – Algarve Coast

Explore the west Algarve at your own pace. Lagos has the best combination of beaches, sea caves, and old-town nightlife. Rent a kayak to reach the sea caves at Ponta da Piedade — golden limestone arches and turquoise water that looks nothing like northern Europe.

Day nine, drive east along the coast. Carvoeiro and Benagil are famous for the Benagil Cave (book a boat tour in advance). Silves has a superbly preserved Moorish castle. Tavira is the most elegant Algarve town — Roman bridge, castle, and genuinely good seafood.

Day 10 – Drive North via Alentejo Coast

Drive north along the Alentejo Coast — this stretch of coastline between the Algarve and Lisbon is almost unknown to foreign tourists. Wild beaches, dunes, and fishing villages. Comporta is achingly stylish. Melides is what Comporta used to be before the celebrities arrived.

Days 11–12 – Porto

Take the Alfa Pendular train from Lisbon to Porto (3 hours) or drive via the Douro coast road. Porto gets better the longer you spend there. Day 11: Ribeira waterfront, Livraria Lello, Clérigos Tower, and port wine tasting in Vila Nova de Gaia. Day 12: São Bento train station (for the tiles), Mercado do Bolhão, the Foz do Douro neighbourhood where the river meets the sea, and dinner at one of Porto’s excellent restaurants.

Days 13–14 – Douro Valley

Drive east along the river into the Douro Valley — the world’s oldest demarcated wine region (since 1756). The road hugs the north bank of the Douro; terraced vineyards rise on every hillside, planted with over 250 grape varieties.

Stop at Pinhão — a small town with a beautiful azulejo-tiled railway station — and take a river cruise to see the valley from the water. Most quintas (wine estates) offer tastings; Quinta do Crasto, Ramos Pinto, and Quinta Nova are particularly visitor-friendly.

Spend a night at a quinta with valley views — one of Portugal’s most memorable accommodation experiences. Return to Porto for departure.

Practical Notes

Transport: Lisbon and Porto are excellent by public transport. Sintra, Alentejo, and Algarve require a rental car. Consider hiring one from Day 4 and dropping it back before taking the train to Porto.

Budget: Two weeks costs roughly €1,500–2,500 per person mid-range, including flights.

Don’t skip: The Museu do Azulejo in Lisbon (the entire history of Portuguese tile art in a stunning convent), the Douro Valley at golden hour, and at least one full afternoon in a pastelaria eating pastéis de nata.