Since you’re starting from Brussels, keep the day simple and leave after 6:00 PM if you can — you’re looking at roughly 3.5–4.5 hours door-to-door once you factor in the airport transfer, security, the flight itself, baggage claim, and the ride into town. From the Brussels side, plan on a straightforward airport departure; from Lisbon’s Humberto Delgado Airport, the easiest arrival into the center is usually a quick metro ride on the Red Line or a taxi/Uber into Baixa if you’ve got luggage and want to save energy. Once you’re checked in, head straight to Praça do Comércio for that first Lisbon moment: wide-open river views, the yellow arcades, and the kind of evening light that makes the whole square feel unreal. It’s the perfect low-effort first stop after travel, and about 45 minutes is enough to get your bearings without rushing.
From Praça do Comércio, walk up toward Rua Augusta Arch — it’s an easy, classic introduction to downtown Lisbon, and worth the small detour even if you don’t go all the way to the top. The arch area is busiest earlier in the evening, but by this time it’s usually lively rather than chaotic, and the surrounding pedestrian streets are great for a slow wander. Continue into Chiado and sit down at Café A Brasileira for coffee or a light dessert; it’s one of those old Lisbon institutions that still feels worth the stop, especially if you want a first taste of the city’s café culture. Expect around €8–15 per person depending on whether you just do espresso and pastry or add something sweeter. If there’s a short line, don’t stress — it moves faster than it looks, and the surrounding streets are pleasant for a few minutes of people-watching.
After that, make your way up to Miradouro de São Pedro de Alcântara in Bairro Alto — it’s an easy uphill walk from Chiado, or a short taxi ride if your legs are done for the day. This is one of the best places for a first sunset view over Lisbon, with the São Jorge Castle skyline, tiled rooftops, and the river stretching out beyond Baixa. Give yourself 30–45 minutes here; it’s best when you’re not in a rush. Then finish with an early dinner at a nearby traditional Portuguese spot in Chiado or Bairro Alto — look for a place serving bacalhau, grilled sardines or sea bass, or a few petiscos to share. A solid meal will usually run €20–40 per person, and if you want the smoothest evening, eat before the later Bairro Alto crowd arrives. For tomorrow, keep the departure flexible: Lisbon traffic can be slow, so if you’re headed out of the city again, leave a little earlier than you think you need and use a taxi or rideshare from your hotel rather than trying to drag luggage through the hill streets.