In the final moments of the Godfather: Part III, Mary, the daughter of Al Pacino’s Don Corleone, is shot on the steps of the grand Teatro Massimo in Palermo. That this emotional finale to the iconic mafia series takes place against the backdrop of one of Sicily’s most historic cultural monuments is fitting.

Since the mid-19th century, Sicily has been known as a hive of Mafioso activity. The government maintained close ties to organized crime families, leading to a web of pervasive corruption and intimidation that waxed and waned for almost a century. During this time, the contrast between Sicily’s identity as the Mafia motherland and a lush lemon grove-dotted retreat was stark. But Sicily’s—and in particular the capital city Palermo’s–romance with this entrenched criminal underworld has gradually been unraveling. Palermo’s once-seedy streets, filled with foreboding vendettas and surprise assassinations at the hands of the Cosa Nostra, are now the scene of vibrant sophistication.
Palermo was once a stopover location, primarily good for seeking out a slab of candy-hued cassata cake en route to the beaches and overpriced resorts of Taormina to the east or the crumbling ruins of Agrigento to the south. Now, it is a worthy destination in its own right, and an exotic, wondrous tale of two cities to boot: it is a deeply historical city with polyglot origins, evidenced in the architectural mash-up of Baroque, Byzantine, and Romanesque influences. It is also looking toward the future, investing in creating a fashionable destination on par with Italy’s other dynamic urban centers. Without sacrificing its rough-around-the edges charm, Palermo is now home to new boutiques and cafes that give it a cosmopolitan flair not uncommon to, say, Rome and Florence.
Palermo’s museums are plentiful, but intimate—and quirky—making it possible to cover a few of the important old-meets-new institutions in just one day. Galleria Regionale della Sicilia’s authenticity is stunning, featuring sculptures and ceramics that date as far back as the Middle Ages and are housed in a 15th-century palace. Another must is Galleria d’Arte Moderna, with its hushed, former-convent setting that belies the contemporary works hanging on the walls. At the Museo d’Arte Contemporanea della Sicilia (which is known as “Riso”), on the other hand, edgy, modern works are showcased in an 18th-century building with an airy café that invites myriad hours of laptop pecking.
Espresso breaks are common in Palermo, especially at the elegant, old world Antico Caffe Spinnato. Here, breakfast begins with a crusty cornetto alla crema served by a formal, dinner jacket-wearing waiter. It’s a mellow starting point for exploring the wide, tree-lined Via Della Liberta. While it certainly doesn’t stack up to haute Milan, this is the spot for browsing high-end boutiques flaunting Champs-Élysées looks.
One aspect of Palermo’s past that has not faded is its robust culinary tradition. Beyond carefree caffeine and gelato breaks, Palermo denizens build meals around simple, traditional street food, from rectangles of fried chickpeas to juicy pane con milza sandwiches filled with thinly sliced meat that resembles bresaola but is, in fact, cow spleen. Antica Focacceria S. Francesco, a popular lunch spot flooded with customers in disorganized lines, is popular for its slabs of namesake bread slathered in tomato sauce, olive oil, onions, and oregano (followed by overstuffed cannolis, of course). It’s a low-key contrast to the modern-style crackling pizza pies that emerge from the oven at La Bufalaccia Ristorante & Pizzeria, one version of which combines cream of broccoli, baked Beefsteak tomato, and black olives.
Although affordable street food is certainly a better fit for residents concerned about debt-addled Italy’s current political instability, Sergio Messina, proprietor of La Bufalaccia Ristorante & Pizzeria, says that Italy’s current economic decline has forced diners to prioritize when visiting restaurants. “Nowadays people are looking for quality, especially when they go out to have dinner. They take care of their spending habits. They don't want to waste their money, and at the same time they need to be educated so they can understand the ingredients that comprise high-quality dishes. This makes it a good time for certain restaurants,” Messina says.
Whether hunger cravings in Palermo are sated via eggplant caponata served at a family-style, upscale restaurant or swordfish pasta from a seafood shack overlooking Mondello Beach, wine is always a constant at the Sicilian table. Sicily’s winemaking roots—established 25 centuries ago—run deep. But it’s only now that high-quality wines are evaporating the long-term stigmas of shoddy bulk production and bottles of fortified Marsala. Sicilian wine is rapidly gaining increased praise stateside, and it dovetails nicely with Palermo mayor Leoluca Orlando’s vision of rescuing Palermo from its Mafia-tinged rotos through a cultural agenda of food, wine, and the arts.
Indeed, the rise of Sicily’s indigenous red grape, Nero d’Avola—along with the still-little-known white grape Grillo—has helped change the local conversation from one of thoughtless, uninspired wines—often made on Mafia-controlled land—to those created with terroir and passion. Northern Italian wine producer Mezzacorona felt so strongly about this new direction, it invested $150 million to help give the Sicilian wine industry a boost, in particular through promoting Stemmari Nero d’Avola, produced at the Feudo Arancio estate, one hour from Palermo.
“Sicilians have wine in their DNA; there are generations of viticulture and winemakers on the island and they take pride in their wines,” Lucio Matricardi, director of winemaking for Stemmari, says. “We believe that Nero d’Avola can become popular for its aromatics and juicy fruit character. The lifestyle, cuisine, art, and history are part of what is transforming Sicily—and through Nero, we’re helping bring attention to this beautiful, bountiful island, too.”
It’s obvious it’s working. On weekends, Palermo’s many enotecas buzz with patrons clamoring for tastes of not just Champagne and Pinot Noir from Piedmont up north, but locally made Nero d’Avola. At Enoteca Butticè, those who can’t snag a table in the cozy joint cram in at the bar and spill out onto the patio with bottles of wine. At the more polished Enoteca Buonivini, brightly lit with walls lined in wine, all that can be heard are popping corks, the scrapes of forks against plates of carpaccio, and animated conversation. Nowhere does Mafia-induced malice brood.