I travelled with friends who grew up in Lisbon and had a car. You can copy the route with a rental, but think of it as a regional road-trip, not a pure city break.
Everywhere felt safe; even late at night we never felt hassled, and street vendors kept to themselves.
Day 1 – Classic Lisbon in One Afternoon
Where we parked: the spotless, guarded garage right under Praça do Comércio (perfect if you’re driving in).
| Stop | Reason | Tip |
| Rua Augusta, Rua do Ouro & Rua da Prata | Lisbon’s historic “Silver” and “Gold” streets of jewellers. | Pop into A Ginjinha nearby for a cherry-liqueur shot (€1.50) |
| Miradouro de São Pedro de Alcântara | Postcard view: castle, red roofs, river. | Starbucks (by Rossio station) stocks the “You Are Here” mug if you collect them. |
| Pink Street (Cais do Sodré) | Instagram-famous bubble-gum-pink lane of bars. | Best for fridge-magnet hunting; livelier Thu-Sat. |
| Dinner on Praça do Comércio | Seafood glory: bacalhau à Brás, grilled octopus, prawns. | Share plates to sample more; mains €15-20. |
Budget check – A litre jug of morangosca (vodka-strawberry) was €5 on a Monday, and cover charges were tiny. Midnight strolls felt completely safe.
Day 2 – Walking-Tour Tuesday
For breakfast: I tried pão-de-Ló (plain-looking sponge, panettone texture, incredibly moist).
- Join a free walking tour from Praça do Rossio (ours started at noon).
- Lisbon Cathedral (Sé) – picturesque and, fun fact, it hosts a nationally-televised mass wedding every June.
- Spot the “AL” signs in Alfama: it highlights local residence, not airbnbs. You also see portraits of residents outside their buildings.
- Save space for ginja in chocolate cups (€1.50 each) at an 80-year-old hole-in-the-wall run by the same owner her whole life.
Day 3 – Sintra Without the Queues
- Uber to Palácio Nacional da Pena (€8) before 10 a.m. to dodge ticket lines.
- Expect Disney colours but modest interiors; the real gem is the woodland chalet hidden 20 min down a bridle path.
- Weather flips fast at 500 m altitude – pack a light jacket.
- Lunch at A Taverna: order the açorda de marisco (seafood-and-bread stew served in a loaf).
- Grab travesseiros de Sintra (“pillows”) warm from Piriquita bakery – one is plenty.
Day 4 – Earthquakes, Gardens & Custard
- Monument to the Discoveries – quick photo stop with the 25 de Abril Bridge backdrop.
- Quake Museum (€21 online) – half science centre, half escape room; don’t miss the church pew earthquake simulator. Great on hot days.
- Lunch at Versailles café (near the Presidential Palace) – try the prawn-filled cod fritters.
- Lisbon Tropical Botanical Garden (€5) – shaded, uncrowded, and attached to Belém’s sights.
- Torre de Belém & legendary pastéis de nata – queue looks scary but moves fast; eat one warm and buy a box for later.
- Visit to the Taras Shevchenko statue near the ethnological museum
Day 5 – Cascais & the “Best Buffet in Portugal”
Morning in Cascais (30 min west of Lisbon)
- Car-friendly, spotless streets, mini-beaches perfect for a stroll or sunbathing.
- Estate-agent window-shopping: studios start at €600k; ocean-view villas hit €4m.
Skip: the McDonald’s “McBifana” – it’s a dry sausage roll in disguise. Instead, snack on beachside prego steak sandwiches.
Afternoon: Boca do Inferno sea-cave viewpoint – dramatic cliffs, cheap parking.
Dinner: Restaurante Pirata (1 hour north, near Torres Vedras) – an all-you-can-dream-of seafood buffet: sushi, shellfish, grilled fish, mountains of desserts plus live keyboard music. Arrive hungry.
Departure Day – Village Farewell & Food Lessons
Lunch in a village taverna confirmed my new rule: always pick the grilled seafood. Pork-and-potatoes was fine, but grilled octopus or squid drizzled with olive oil is Portuguese perfection.
Would I Do It Again?
Absolutely – but with a rental car so I can mix Lisbon’s classics with day-trips to Sintra, Cascais and northern villages. Keep your appetite for seafood, carry small change for ginja shots, and don’t fear the late-night wander: Lisbon after dark is as welcoming as it is photogenic.