Calogero’s, a Lounge with Class (and a Touch of Sass)

The latest venture by Santino’s owners hints at the bar’s history as a Bay View speakeasy during Prohibition.

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Eat/Drink

Bay View’s newest lounge, Calogero’s (338 E. Bay St.), occupies a building with a long history. The 1890s structure has housed corner bars throughout its life. During Prohibition, it was a speakeasy serving ice cream up front and illicit libations in the back room. Calogero’s co-owner Santo Galati wants to tap into that storied past. “We tried to get a feel of the ‘30s—that history helped the formation of our plans,” he said.

Nearly a decade ago, Galati and business partner Greg Huber opened a popular restaurant just up the street from Calogero’s, Santino’s Little Italy (352 E. Stewart St.). Like the new joint, Santino’s resulted from the total gutting and reimagining of a derelict corner bar. The interiors of both venues were executed by MKE Design Build, but each has its own special flair. Where the screens at Santino’s run with a loop of Sophia Loren films, Calogero’s screen features the Robert Redford version of The Great Gatsby with the sound muted. Expect to hear Frank Sinatra and friends at conversational volume.

Cherub sconces are among the gilded accents of Calogero’s black and red color scheme. Most of the lighting fixtures are Italian and many are antique. The front room’s black marbled bar with red upholstered seats is faced by intimate alcove booths, ideal for first dates and intimate discussions of all sorts. It’s easy to imagine Carol Lombard huddling with William Powell over a martini at Calogero’s. The vibe is baroque but never over the top, retro but not campy. A large portrait of Al Capone looks on approvingly. The profusion of tightly framed portraits of women’s faces turns out, on close inspection, to be cut from blocks of wallpaper.

The backroom is also painted black, with a 200-year-old Italian chandelier and a stained-glass window that has migrated across several Milwaukee bars over the past century. But with its Tiki Fortune and other online slot games, it calls to mind a classier joint in Las Vegas. A covered, fenced-in patio out back will be open in time for warm weather.

Calogero’s is light on food compared to Santino’s. The tiny kitchen serves an antipasti platter (and a vegetarian version), Tuscan flatbread sandwiches, a flatbread pizza with fig jam, honey and cheese along with other appetizers. Most of the ingredients are sourced from Italy or Wisconsin.

However, the drink menu is expansive. Among the 16 martinis are the Fico Nonino (honey vodka, Nonino Amaro, fig liqueur) and the Tiramisu (vanilla vodka, tiramisu liqueur, espresso, cocoa dust). There are at least 25 other cocktails including the Sophia Loren (vodka, amaretto, lime juice, Italian cherry soda) and an Old Fashioned Italiano (brandy, amaro, splash of soda). The menu goes on to embrace draft and bottled beer, non-alcoholic and ice cream drinks, a raft of Italian herbal liqueurs and—no surprise!—a long wine list.

Calogero’s is an easy place to love, and a reflection of its owners. “We wanted to make a place where we’d like to go,” says Huber.