It’s not quite the razor’s edge, but a walk along Rua da Misericórdia in Lisbon is a walk on the slim frontier that separates Bairro Alto and Chiado, two very different worlds in the heart of the Portuguese capital.

To the west, bohemian Bairro Alto is the graffiti-sprayed warren of vintage stores, hole-in-the wall restaurants, dive bars and live-music venues, where noisy throngs fill the narrow streets until the wee hours.

Free to enter, Carpe Diem Arte e Pesquisa plunges you into a gloriously faded 16th-century mansion whose maze of aristocratic rooms brim with sweeping staircases, huge fireplaces, panels of blue-painted azulejo tiles, and intricately carved plaster ceilings in varying states of dilapidation. These haunted spaces serve as galleries for exhibitions and site-specific creations by a rotating roster of international contemporary artists that has included the Cameroonian painter Barthélémy Toguo, the Albanian multimedia provocateur Adrian Paci and Portugal’s own tree-branch installation specialist, Gabriela Albergaria.

Short on physical comfort but brimming with traditional Portuguese comfort food, Antigo 1° de Maio has drawn generations of discerning Lisbonfolk to its pocket-size room of tiled walls, checkered tablecloths and stiff wooden chairs. The portions are copious from beginning to end, starting with appetizers like escargot or melon with cured ham, moving on to the likes of grilled pork tenderloin and roasted sardines, before finishing in a wave of sweets that includes egg pudding and mango mousse. A three-course meal for two is about 40 euros.

For a digestive, try a cup of ginja (4 euros), a Portuguese cherry liqueur, in the equally small, rustic and jam-packed confines of Tasca do Chico. Then get out your handkerchief. The bar is a haven of Fado, Portugal’s melancholy seafaring folk music, and stars like Raquel Tavares and Mariza have been known to stop by incognito for impromptu performances. Better still, there’s no cover.

The extra money will be useful in Chiado, east of Rua da Misericórdia, which beckons with fashion boutiques, design emporiums, centuries-old churches, historic theaters and the city’s top gastronomic palace.

Keen to eat from a platter decorated with half-unicorn men and zebra-bodied women cavorting in a garden of exotic butterflies and dragonflies? The boutique of Vista Alegre — a Portuguese manufacturer of high-end porcelain, ceramics and crystal since the 19th century — showcases a line of dinnerware decorated by the French fashion designer Christian Lacroix. Mythical creatures and other exotic fauna (and flora) animate the series, from dessert plates (29 euros) to teapots (180 euros).

Or let Belcanto serve you. The decades-old institution was reopened in 2012 by the Portuguese celebrity chef José Avillez and already has two Michelin stars, the only restaurant in Lisbon with that honor. Centered on nouveau Portuguese cuisine, the à la carte menu might feature suckling pig with orange and potatoes, beef loin with bone marrow and garlic purée, or sea bass with seaweed and bivalves. Tasting menus are available for 125 and 145 euros.

For a recap and a nightcap, survey the glowing city from the top-floor terrace bar of Hotel do Chiado, which was designed in part by the Pritzker Prize-winning Portuguese architect Álvaro Siza Vieira. With a port-wine mojito (11 euros) or frothy Chiado Lovers cocktail (vodka, coconut cream, cocoa cream and hot sauce, 10 euros) in hand, you can spot the battlements of the hilltop Castle of São Jorge, the Tagus River flowing toward the Atlantic, and the rest of Lisbon: dirt-cheap, gold-plated and beyond.