Lisbon looks compact on a map and is not, because the map is flat and the city is not. Seven hills, marble pavements polished slick by two centuries of feet, and staircases where you expected a street. This is the first thing I explain to clients, and it changes which hotel I recommend.
Chiado and Baixa
The heart of the city, and the easiest base for a first visit. Theatres, bookshops, the best concentration of restaurants, and mostly level walking through Baixa before the hills begin. If you want to step out of your hotel and be somewhere immediately, stay here.
Príncipe Real
My favorite for a longer stay. Leafy, residential, full of design shops, small wine bars and a Saturday market, ten minutes downhill into Chiado and a determined ten minutes back up. Quieter nights than Chiado without feeling far from anything.
Alfama
The oldest quarter: tiled facades, washing lines, fado drifting out of doorways, and the steepest lanes in the city. Extraordinary to walk through and demanding to live in — taxis often cannot reach the door and you will finish each day with a climb. Wonderful for travelers who like an atmospheric maze, hard for anyone with mobility concerns.
Avenida da Liberdade and Lapa
The grand hotels, the flagship shops, wide boulevards and calm evenings. Lapa is residential, elegant and very quiet, with river views and a hill between you and dinner. Both suit travelers who would rather take a taxi than a staircase.
Belém
Beautiful for a half day — the monastery, the tower, the original pastéis de nata still warm — and too far out to sleep if you have three days.
What to see first
Start high and walk down. A viewpoint in the morning, Alfama and the cathedral before the tour groups, lunch at the Time Out market or a neighborhood tasca, Belém in the afternoon, and fado in a small room in the evening — booked, because the good places seat thirty people. Save one morning for the tram 28 route early, when it is transport rather than a queue.
Sintra, and the mistake everyone makes
Sintra is worth a full day, not a rushed morning, and it should be arranged with a driver or with the earliest possible train. The palaces sell timed tickets, the town's roads gridlock by mid-morning, and the difference between a Sintra day that feels magical and one that feels like a car park is entirely about the hour you arrive. Cascais and the coast make a lovely afternoon on the way back.
How many days do you need?
Three full days in the city, plus one for Sintra. Add two more and Portugal opens up: Porto and the Douro Valley by fast train, the walled towns of the Alentejo by car, the Algarve coast in the south. Portugal is the country where clients most often tell me afterwards that they wish they had stayed a week longer.
When to go
March to June and September to October are perfect. July and August are hot and busy, though Lisbon handles summer better than inland Spain or Italy. Winter is mild, grey in spells, inexpensive, and the food is just as good.
My longer guide to planning a trip to Lisbon — arrival from the airport, neighborhoods, what to book ahead and local dining hours — is linked below.