SET ATOP SEVEN HILLS overlooking the Tagus River, Lisbon comprises peaks and valleys packed with ample opportunities for heart-capturing vistas and rousing after-sun activities. The Portuguese capital’s concentrated and well-connected central zones make it easy to zigzag across the city for a few hours of post-work amusement.

Before the sun fully sets, hop on historic Tram 28 to the Alfama District, the city’s oldest, a former working-class neighborhood where a recent revival sprouted chic watering holes while retaining the spirit of the streets. Located just outside the walls of the Castelo de São Jorge, the Winebar do Castelo’s intimate tasting room serves small plates of cheese and charcuterie to complement the region’s best wines. Alfama is also one of the best places to catch fado, Portugal’s informal musical performance characterized by projected singing and an accompanying guitar. When strolling the streets, you’ll notice chalkboards advertising show times, but you’ll find the most authentic presentations at A Baîuca and Clube de Fado.

A more raucous party scene takes place a few hours later in Bairro Alto, just west of the business district of Baixa. Tiered seating at alleyway cafés gives you a front-row seat to the barhoppers who frequent the area during the evening hours. Join them for a round at one of Bairro Alto’s bars like Cinco Lounge cocktail bar, or catch some local music at Galeria Ze Dos Bois (aka ZDB), part art gallery, part live music venue.

Just north of Bairro Alto discover Chiado and Principe Real, home to Lisbon’s gay scene. For €10 (about $12), hit up Trumps, the city’s largest gay club, or stop in at Finalmente Club any day of the week for its famous drag show, which takes place at a reasonable hour of 3 a.m.

Regardless of where you choose to spend your evenings, make a point to take in a drink at one of Lisbon’s miradouros, or lookout points. The Miradouro de Santa Catarina boasts stunning San Francisco-esque views over the river and the 25 de Abril Bridge and on to the statue of Cristo Rei in the distance. A café, restaurant and front lawn of the Pharmacy Museum, all of which serve beverages well into the evening, enhance this particular viewpoint’s allure.