Madeira's night happens almost entirely in Funchal, and even there it is bars and a casino rather than a club circuit — outside the capital most villages are dark and quiet by ten.
Rua de Santa Maria and the Zona Velha
Funchal's old town street, known for the painted doors, is lined end to end with bars and restaurants and is where the evening concentrates. It runs from near the Mercado dos Lavradores down towards the Barreirinha, all walkable.
Casino da Madeira
On Avenida do Infante, with the gaming floor — slots, blackjack, roulette, baccarat, poker — plus restaurants and the Copacabana club, which is the closest thing Funchal has to a reliable late nightclub. Operated within the Pestana group; take ID.
Marina do Funchal and Avenida do Mar
The waterfront strip below the old town has terrace bars facing the moorings, busiest before dinner and around cruise-ship turnarounds. Calmer and more mixed-age than Santa Maria; a five-minute walk between the two.
Poncha in Câmara de Lobos
The fishing town about 10 km west of Funchal is where poncha — aguardente de cana, honey and citrus, stirred with a wooden mexelote — is taken most seriously, in small bars around the harbour. Go by bus or taxi and do not drive after; it is much stronger than it tastes.
Do not plan a night outside Funchal
Porto Moniz, Santana, São Vicente and the levada villages have restaurants but effectively no bar scene, and the mountain roads are long, dark and winding. If you want an evening out, base yourself in or near Funchal for those nights.