South Boston is a town abundant with symbolism, and, for better or worse, it's hard not to get caught up in one mythical version of the ballyhooed neighborhood when walking along the main thoroughfare of Broadway on, what else?, a bar crawl. But which Southie do we mean? Evidence of the quickly developing new Southie is in abundant display no matter which way you look – cute cafes, salons, gleaming new condo – but there's space to let your mind wander into the past, particularly along the side streets that branch off from the main artery. Unfortunately, what you won't find much of any more is anything in the way of a gritty old neighborhood bar, with only a few redoubts peppered along the way. That doesn't mean it's not a worthwhile destination for a drinking jag.
New kid on the block
Moonshine 152, 152 Dorchester Ave., South Boston, 617-752-4191, www.moonshine152.com
You might begin at Moonshine 152, the new outfit that's tagged in to take over the Franklin Southie space. If you're missing the Franklin, you could close your eyes just so and it wouldn't feel much different, looks-wise anyway. While the cocktails coming over the bar can be hit or miss, the New Classic hits the mark with its spirits-forward blend of rye, Chartreuse, Aperol, cherry syrup, and Bitermens Boston Bittahs. You'll want to try the Korean BBQ Tacos, made with beef shortrib, asian pear kimchi and candied ginger aioli to fortify you for the journey ahead.
A familiar feel
Stephie's in Southie, 130 Dorchester Ave., South Boston. 617-345-5495
Depending on how previous you are about these sorts of things, you could easily grouse about the presence of Stephi’s in Southie's as a harbinger of things to come. And, indeed, the offshoot of the Newbury Street classic is certainly rather “Newbury Street” But inside you'll find a familiar product in a nice, comfortable space, and you probably won't get in a fistfight. What's better than that? On the plus side they're serving Southie's own Grand Ten Distilling spirits on the bar, like in the After School Special, made with Fire Puncher vodka, citrus and agave, muddles strawberries and ginger beer.
Keep it old school
Croke Park/Whitey's, 268 Broadway, South Boston. 617-464-4869
While it's been a brutal time for the dive bars of Southie in the past few years, and around the city in general for that matter – RIP to the Corner Tavern and the Quencher, to name just a few around these parts – you won't find a better example of Old Southie than Croke Park/Whitey's. While you might feel out of place at first, especially if you're a big baby, the rules in this neighborhood local dive are the same anywhere else: Don't act like a jerk and you'll be fine. Take your turn at the pool table, and order a domestic and a shot of whatever.
Master the crowds
Loco Taqueria & Oyster Bar, 412 Broadway, 617-917-5626. www.locosoutboston.com
The Lincoln, 425 Broadway, 617-765-8636, www.lincolnsouthboston.com
Once you've had a quiet drink or two at Whitey's, a few blocks up you can hurl yourself back into the Southie throngs at Loco Taqueria & Oyster Bar and The Lincoln. Both are over-sized, although one gets the impression that no matter how big they were, they'd constantly be crowded, particularly on the weekend. The wait for a table at either might take all night, and the bars themselves are often three deep, but there's no better spots to get a slice of the young Southie crowd that's come to define the area. At Loco, which specializes in – you guessed it – tacos and raw bar, there's a long list of tequilas that customers nonetheless obliterate in fruity margaritas, but some fine sippers can be had. At the Lincoln you might stick to some of the beers, particularly when long lines make waiting for a cocktail a chore. But options like the Battle of Puebla, made with mezcal, Ancho Reyes, Amaro Nonino, and crème de cacao are typically worth the wait.