Cascais empties of day-trippers by sundown and reveals a quieter drinking scene than its location near Lisbon suggests. The marina and the streets behind it have the densest cluster of bars, and the small lanes inland from Praça 5 de Outubro hold the older, more local-feeling spots.
Bar do Guincho at the beach end of the coast road is the obvious sundowner — a wooden-decked terrace with cocktails and the Atlantic in your eyes. Chequers is a long-running English-Irish pub near the central square popular with expatriates and English-speaking tourists. For an aperitif at the start of an evening, the Hotel Cidadela bar inside the fortress walls is hard to beat — sit in the courtyard with a port wine as the sun goes down. Café Galeria House of Wonders doubles as a coffee shop by day and a vegetarian bistro and wine bar by evening.