Lisbon and Madeira in 8 Days: A Day-by-Day Itinerary

Portugal · 8 days

Four days on seven hills: trams, tiled walls, the monastery at Belem, and evenings in Alfama with fado.

Day by day

Day 1 · 6 placesLanding and a first evening in Alfama

airport → center on the red metro line, 20 minutes

Alfama
The one neighborhood that survived the 1755 earthquake: stairs, laundry overhead, and fado coming out of open doors after nine.
Aeroporto Humberto Delgado (LIS)
Where you land. The red metro line starts right at the terminal and takes twenty minutes to downtown.
Sé de Lisboa
The cathedral from 1147, built like a fortress right after the city was taken back from the Moors. Tram 28 grinds uphill past its door.
Miradouro de Santa Luzia
A terrace with an iron trellis and bougainvillea above the red roofs of Alfama. The tile panel on the wall shows Lisbon before the earthquake.
Clube de Fado
Fado is a concert, not dinner music: the lights go down, the room goes quiet, two guitars. Book a table; the singing starts around 9:30.
Miradouro da Senhora do Monte
The highest viewpoint in the city and almost no crowd: all of Lisbon, the castle off to one side, and the bridge at sunset.

Day 2 · 5 placesBelem: the monastery, the tower, the custard tarts

tram 15 from downtown, 25 minutes

Mosteiro dos Jerónimos
A monastery paid for with a tax on pepper: stone lace in the Manueline style, and Vasco da Gama buried inside. The cloister is the best part.
Torre de Belém
A 1519 watchtower standing in the water, where ships left for India. Inside it is cramped and crowded — it looks better from outside.
Padrão dos Descobrimentos
A stone ship’s prow with a line of explorers on it, 170 feet tall. An elevator goes up; from the top you see the marble world map laid into the square.
Museu Nacional dos Coches
The best collection of royal carriages anywhere: gilded 17th-century coaches the size of a room. Kids stare, and so do adults.
MAAT
A white tiled wave on the riverbank — people walk over the roof, and there is contemporary art inside. Even skipping the art, the walk back along the river is worth it.

Day 3 · 4 placesSintra: palaces in the fog

train from Rossio station, 40 minutes, then bus 434

Palácio da Pena
A yellow-and-red palace on a summit that looks made up: Moorish domes, Gothic towers, and fog that rolls in by lunchtime.
Cabo da Roca
The westernmost point in Europe: a 500-foot drop and open ocean all the way to America. The wind will take your hat.
Quinta da Regaleira
A Freemason’s estate with a puzzle for a garden: an initiation well spirals 90 feet down, with tunnels leading off to grottoes.
Castelo dos Mouros
A 9th-century Moorish wall running along the ridge. From it you see Pena Palace across the valley and the ocean beyond. Steep climb, a quarter of the crowd.

Day 4 · 7 placesLisbon itself: hills, market, LX Factory

all day on foot and on tram 28

Castelo de São Jorge
A Moorish fort on the top hill: walls you can walk, peacocks in the yard, and the whole city from the river to the bridge.
Praça do Comércio
A square that opens straight onto the river — the king’s ships docked here. All of pedestrian Baixa starts at this arch.
Time Out Market
The old Ribeira market handed to the city’s best cooks: thirty kitchens under one roof and shared tables. Expensive by local standards and worth it.
LX Factory
A 19th-century weaving mill under the bridge, now a block of workshops and bars. The Ler Devagar bookstore, with a printing press up to the ceiling, is reason enough.
Igreja de São Roque
A gray box from the street; inside, the most expensive chapel of its day — built in Rome, blessed by the Pope, taken apart and shipped here. Free to enter.
Miradouro de São Pedro de Alcântara
A two-level terrace facing the castle. The yellow Gloria funicular climbs to it, and the evening in Bairro Alto starts here.

Day 5 · 4 placesFlight to Madeira and a first evening in Funchal

Lisbon → Funchal, 1 h 45 in the air · pick up the car at the airport

Aeroporto da Madeira (FNC)
An airport on concrete stilts over the ocean — the landing itself is a sight. Rental cars are in the terminal, and Funchal is twenty minutes away.
Zona Velha do Funchal
The old town, where every door is painted by an artist. People eat here in the evening, and the cable car starts at the end of the street.
Sé do Funchal
A cathedral from the late 1400s, as old as the settlement itself. The ceiling is Madeiran cedar — a tree the island no longer has, and a ceiling you will not see anywhere else.
Praia Formosa
The city beach of black pebbles, ten minutes west: clear water, a rocky entry. A first swim in the Atlantic right off the plane.

Day 6 · 3 placesThe mountains: Arieiro and a levada walk

~40 miles of switchbacks, above the clouds

Pico do Arieiro
The island’s third-highest peak, 5,965 feet, and the road goes all the way up. At sunrise the clouds lie below you with only the other peaks sticking out.
Levada do Caldeirão Verde
A trail along a 16th-century irrigation channel: four miles through laurel forest, four tunnels, a waterfall at the end. Bring a flashlight.
Teleférico do Funchal
A cable car from the waterfront up to Monte: fifteen minutes over rooftops and gardens. A second cable car brings you down to the botanical garden.

Day 7 · 5 placesThe north and the west coast

~75 miles around the island through Porto Moniz

Cabo Girão
The highest sea cliff in Europe — 1,900 feet — with a glass-floored platform hanging over it. Tiny terraced gardens sit at the bottom by the water.
Praia do Seixal
Black volcanic sand under a green wall with waterfalls coming down it. You can swim when the ocean is calm, and photograph it any day.
Fanal
A plateau of thousand-year-old laurels with trunks twisted by the wind. When the fog comes in the forest looks like a stage set — that is what people come for.
Porto Moniz
Natural pools in hardened lava at the northwest corner of the island: the ocean pours over the rim, and the swimming inside is calm.
Câmara de Lobos
The fishing town Churchill painted: colored boats in the bay and bars serving poncha, the local drink of honey, lemon and sugarcane rum.

Day 8 · 3 placesOne last morning, then home

Funchal → airport, 20 minutes · drop the car

Mercado dos Lavradores
A market from 1940: ten kinds of passion fruit, scabbardfish with monster teeth, and vendors in embroidered aprons. Fruit tastings are not free — ask the price first.
Monte Palace
A tropical garden on the slope: Japanese ponds with koi, 500-year-old tile panels, and a mineral collection. Walk back down through the paths.
Blandy's Wine Lodge
A Madeira wine lodge in a former monastery: barrels sit under the roof warming in the sun for twenty years — that is how the wine is made. The tour with tasting takes an hour.