14 Days in Portugal: Lisbon, the Algarve, the Douro & Porto

A 2 week Portugal itinerary is long enough to stop feeling like a visitor. Two weeks gives you the trams in Lisbon, the cliffs of the Algarve, the cork-oak plains of the Alentejo, the wine terraces of the Douro and the port lodges in Porto, with time to sit down for lunch in each. This 14 day Portugal itinerary runs in one direction: Lisbon (3 nights) → the Algarve (3 nights) → Évora (1 night) → Coimbra (1 night) → the Douro Valley (2 nights) → Porto (3 nights). You fly in to Lisbon and home from Porto, so you never cover the same road twice.

The longest single move is about 3 hours, and most days have one morning of sightseeing and one short transfer. The south gets three full days, enough for the coast and one empty afternoon. The Douro gets two nights, which is the difference between a tasting and a valley. For the full set of Portugal trips, see our Portugal page.

Times are approximate. Check train timetables and flights for your dates before you book.

Your driver meets you at Humberto Delgado Airport and brings you into the historic centre along the Tagus. Settle in, then walk down to the water. As the light softens, climb to a miradouro, one of the city's viewpoints, and watch the hills turn to terracotta and tile below you. A glass of vinho verde is the right drink here.

Day two is a walk through three layers of the city. Alfama is the oldest quarter, with lanes barely wider than a car. Chiado is the café and bookshop district, and Baixa is the grid of streets rebuilt after the 1755 earthquake. End at Commerce Square, where the river opens out in front of you. Save the afternoon for a pastel de nata and a slow walk back.

Day three is Sintra, about 40 minutes west. Pena Palace is the one from the photographs: a painted fantasy on a wooded ridge, with canary-yellow walls. Go early. On the way back, stop in Belém for the Jerónimos Monastery and the Tower of Belém, both tied to the age of exploration. For more on the city, see our Lisbon guide.

The first-class train south from Lisbon takes about 3 hours and crosses the Alentejo's cork-oak plains. Your driver meets you at the station and takes you to a coastal hotel on the central Algarve. Limestone cliffs the colour of burnt honey, water in shades of green and blue, and a seafood lunch on a terrace. The pace changes the moment you arrive.

Day five is the big coast day. Walk the old walled centre of Lagos, then go to Ponta da Piedade, where the cliffs break into arches and sea stacks. Go by kayak early in the morning if you can. Continue to Sagres, a fortress on a flat headland linked to Henry the Navigator, and finish at Cape St. Vincent, the south-westernmost point of mainland Europe. There is a lighthouse on a black cliff, and the Atlantic on three sides.

Day six is left empty on purpose. Take a boat into the Benagil sea cave, walk the lanes of the old Moorish town of Albufeira, or do nothing at all. If you want the first half of this trip in a single week, our South of Portugal tour covers Lisbon, Sintra and the Algarve.

The Alentejo is wide, dry and quiet, with cork oaks, olive groves and very little traffic. Évora is its main town, a UNESCO World Heritage city of old walls and narrow lanes. A Roman temple stands in the middle of town, next to the cathedral. Walk the streets after dinner, when the lanes are quiet and the cafés spill out onto the squares.

The Chapel of Bones is small and strange. Its walls are lined with the bones of thousands of people, and it takes about ten minutes. Before you leave in the morning, drive out to the Almendres Cromlech, a field of standing stones older than Stonehenge. For the shorter version of this loop, see our 10 day Portugal itinerary.

From Évora it is about 3 hours north to Coimbra. The city climbs a hill above the Mondego river, and Portugal's oldest university sits at the top. The university was founded in 1290 and settled in Coimbra for good in 1537, and it still sets the rhythm of the place.

The reason to stop is the Joanina Library. The library is spread over three floors, with the gilded baroque shelves on the top one, and a colony of bats is said to keep insects away from the books. Entry is by timed ticket, so book ahead. Then walk down through the old town to the river. Coimbra is liveliest in term time, from autumn to late spring, when students in black capes fill the streets.

The Douro is one of the oldest demarcated wine regions in the world, regulated since 1756, and its terraced vineyards are a UNESCO World Heritage Site. The road from Coimbra climbs through granite hills and pine forest, then drops toward the river near Pinhão. Stay on a quinta, a working wine estate, so you can walk the rows at the end of the day.

The second full day is slow on purpose. A family quinta, a tasting of port and the dry reds the valley now makes, a long vineyard lunch, and an hour on the river by boat. From mid-September to mid-October the harvest is on, and the estates are at their busiest. Our North of Portugal tour spends two nights at a wine estate in this same valley.

Porto is steeper, greyer and more lived-in than Lisbon, all granite and tiled facades. Arrive, check in near the historic centre, and walk down to the Ribeira while the light turns copper on the river. The Dom Luís I bridge crosses above you, with the metro running across its upper deck.

Give one morning to the classics: the tiled hall of São Bento station, the Lello Bookshop and the Clérigos Tower. Then cross to Vila Nova de Gaia, where the port lodges age their wine in cellars on the south bank. Save the last afternoon for Foz do Douro, where the river meets the Atlantic. If you want a shorter trip built around the same towns, Essence of Portugal covers Lisbon, Sintra, Porto and the Douro in a week, and Best of Portugal adds Coimbra. For more on the city, see our Porto guide.

Lisbon: Baixa, Chiado or Príncipe Real, on foot to most sights, with taxis for the hills. Algarve: a hotel on the central coast, close enough to Lagos and Sagres for day trips. Évora: inside the walls. Coimbra: on the river side of the old town, near the university but away from the steepest steps. Douro: a quinta near Pinhão, because the estate is the point. Porto: the Ribeira or the streets just above it, for river views and a short walk to São Bento.

April to June and September to October suit this route best. The days are long, the sea warms up from late spring, and the Douro harvest runs from mid-September to mid-October. July and August are hot inland, and Évora and the Douro can climb past 30°C. November to March is quieter and cheaper, with more rain in Porto and the north. For the bigger picture, read our Visit Portugal guide.

No time for the Algarve? Drop it and take the first-class train from Lisbon to Porto, about 3 hours, then spend the extra nights in the Douro. Short on time? Our 7 day Portugal itinerary keeps Lisbon, Sintra, Porto and the Douro and leaves out the south and Évora. Got three weeks? Add the Minho region north of Porto, or a second week on the Algarve coast. Want a beach and a wine valley with less driving? Stay four nights on the Algarve and skip Coimbra.

We are a small team, so we plan each two-week trip ourselves, with one planner who stays your contact from the first email to the flight home. We book the train seats, arrange private transfers between Lisbon, the Algarve, Évora, Coimbra and Porto, and match you with guides in each city who know their own neighbourhoods. Timed tickets for Sintra and the Joanina Library go in early. Tell us your dates and how you like to travel, and we will build the rest.