My experience of going out for Italian food in Boston typically runs something like this. Invariably, the setting is the North End; with a hundred or so Italian eateries crammed into a radius of less than half a square mile, that’s pretty much a given. A walk through the neighborhood’s narrow, bustling sidewalks is followed by dinner in a small, crowded restaurant with a menu not unlike that of every other restaurant in the area. There’s nearly always a bottle or two of robust Italian wine, but rarely cocktails. Maybe that’s because wine is such a traditional accompaniment to an Italian meal. Then again, some of those places don’t even have bars to sit at, let alone drink lists. That’s understandable – real estate is at a premium in the North End, and most eateries justifiably devote more space to their dining areas. Cinquecento refreshingly stands that model on its head.
For starters, it’s in the South End, not the North. Far from the tight confines of Boston’s oldest residential neighborhood, Cinquecento is blessed with plenty of space. (There’s even – gasp – a parking lot.) An illuminated staircase leads up to an expansive, thoughtfully arranged dining area.
There’s a mix of long, communal tables, ideal for groups, and smaller booths for a more intimate evening. Pillars throughout the dining room are decoratively lined with bottles of classic Italian aperitifs like Campari and Aperol.
Yet for all its contemporary accents, Cinquecento exudes a certain old-world charm. The rustic hardwood floors, exposed brick, and reclaimed ceiling beams project a sense of timelessness amid the fashionable modern style.
But Cinquecento’s bar area may be its most striking attribute.
The long, curvy bar is surrounded by about 20 seats. Its gorgeous surface, made from Italian marble, is lined with fresh ingredients and oversize Aperol bottles. Additional tables and booths reside beyond the bar, in front of tall picture windows.
It may be unusual to see a Boston Italian restaurant with such a prominent bar area, but it’s ideal for a place that endeavors to be not only an upscale eatery but a casual, neighborhood gathering spot. And if Italian restaurants in this city aren’t typically known for their bars, they certainly aren’t known for their cocktail menus. This might be what truly sets Cinquecento apart.
Now don’t worry – there’s plenty of wine here if you want it. Cinquecento’s extensive wine selection spans all manner of grapes, styles, and regions.
But with all due respect to vino, Cinquecento’s cocktail program is dynamic, original, and creative. The spirit of the mother country infuses the drink list, which makes liberal use of Italian liqueurs, mixers, and the fresh herbs that line the bar. There’s even a cocktail made with grappa, the most iconic and, some would say, least palatable of Italian liqueurs (I was dissuaded from ordering it by my friend Tania, who described it as “straight-up nasty pants”).
I opted for something more approachable.
“Pompelmo” is Italian for grapefruit, and this refreshingly sour Pompelmo cocktail combines grapefruit juice, tequila, rosemary, smashed cucumber, and sea salt. Softly herbal with a cool freshness from the cucumber, the tequila adds a distinctive bite.
The Whiskey Alla Moda is a bold drink with a mild sweetness, mixing Old Overholt rye with a house-made basil citrus syrup.
The Calientie Arancis is kind of like a grown-up margarita. Made with Lunazul tequila, spiced blood orange, Aperol, and smashed ginger, it’s a vibrant, fruity drink with a little kick to it. The Aperol balances out the flavors with a hint of bitterness.
As evidenced by the bottles stationed throughout the bar and restaurant, Aperol is a popular ingredient at Cinquecento, as is the similar aperitif Campari. The bitter Italian spirits factor into a number of the drinks, most notably the Negroni, a classic that originated in Florence in the early 20th centuryand has enjoyed a spectacular resurgence. Cinquecento even offers a Negroni “flight,” featuring the original Negroni and two variations.
This institutional fondness for the Negroni is something I probably should have accounted for when I asked the bartender, Phil, about the “Impazzire” option. Translating loosely to “go crazy,” this is your chance to simply rely on the bartender’s whims for a handcrafted cocktail. “How about a Negroni?” he quickly asked. Nanoseconds later he was already mixing the ingredients, leaving me no chance to politely explain that I’m not a huge fan of the immensely popular drink. But I’m glad I held my tongue. Phil put a couple of interesting twists on the classic – swapping out gin for bourbon and Campari for the less bitter Aperol. His bourbon Negroni was more in the neighborhood of a Manhattan, with a subtle orange essence from the Aperol.
Cinquecento’s dinner menu reflects that same sense of creativity and think-on-your-feet spontaneity. Led by chef Justin Winters, Cinquecento lives up to its name as a Roman “trattoria” – a restaurant focusing more on regional and local recipes than on mainstream Italian staples. In other words, it’s not as predictable as heaping portions of pasta smothered in red sauce and cheese. Among the entrées, Rigatoni Alla Norcia is made with fennel sausage and cognac cream, while a veal tenderloin is wrapped in prosciutto and served with cabbage fondue and marsala sauce.
My friend Tania and I stuck with the antipasti, and she suggested the Carciofi Alla Giudia. These fried baby artichokes, served with lemon and salsa verde, are crispy and delicious, but very garlicky. Ordering these bad boys is inadvisable if you’re on a date; better to share them with a friend (or if you need to ward off vampires).
And then, a special surprise! Executive sous chef Caleb brought us a house-made lardo, a dish he’d been trying out in the kitchen but that hasn’t made it onto the menu. Lardo, if you don’t know, is made from a layer of back fat from a pig, cured and seasoned with salt, herbs, and spices. Draped over baked bread and topped with fresh ramps and chilis, it made for a smoky, unusual, and tasty treat.
Now in the interest of full disclosure, Tania is engaged to chef Winters, so we probably got a little extra attention while we were there. I doubt the chefs typically emerge from the kitchen to share new recipes with random guests. Still, it’s kind of cool to know that they’re back there experimenting, coming up with new recipes based on the ingredients they have access to on a given day.
Now what goes best with back fat? Raw meat, obviously. So next up was the Carpaccio Carbonizatti. This phenomenal charred beef carpaccio is bursting with flavor, served with hazelnuts, parmigiano crema, and grilled bread. Perfetto!
We closed out with the evening’s antipasti special – pickled ramps and mushrooms served with a zucchini pesto. Now I’m no lover of mushrooms and wouldn’t have chosen this on my own. But for the second time that night, I was pleasantly surprised. The mushrooms absorbed the rich, earthy flavors of the zucchini pesto, and the ramps, or wild leeks, added an aromatic crispness.
When I returned a week later to round things out with another drink, I found Phil again working the bar. And while it was only my second visit to Cinquecento, I felt, oddly enough, like a regular. Phil didn’t even hand me a menu, and instead we talked about cocktails that would be suitable for that particular evening. “It’s nice out,” he noted. “Want something spring-y? Bourbon?” he asked. I readily agreed, and he proceeded to mix up an excellent drink that even caught the attention of a server passing by, who inquired as to its ingredients.
It’s a play on a Bourbon Smash,” Phil said of his elaborate drink, which combined bourbon, muddled mint, lime, Aperol (of course), and a touch of basil simple syrup, finished with a little soda and a mint leaf garnish. “The Aperol goes well with the mint,” he explained; it also brought a subtle undercurrent of bitterness to this fresh, aromatic cocktail, which was well suited to the warm, spring weather we were experiencing.
It’s pronounced chin-kwe-CHEN-to. If that doesn’t roll off the tongue, you can call it by its English translation – 500, which also reflects the number of its Harrison Avenue address. That’s a fair distance from the city’s most famous concentration of Italian restaurants; but in terms of style, it’s about as far as you can get. I know it’s unfair to paint the entire North End with one broad stroke; there’s certainly some good Italian food and engaging dining experiences to be had there. But there’s a lot of similarity, too, and I always appreciate the chance to try something different.
Cinquecento’s cocktail program alone distinguishes it from its peers, but the improvisational spirit behind the bar begins in the kitchen. Chef Justin Winters and his team seek out seasonal ingredients for an inventive, eclectic menu imbued with a sense of authenticity not often found in Americanized Italian eateries. You can have lasagna anywhere; garganelli with red wine octopus ragu and squid ink is a bit harder to find.
An impressive bar area and selection of craft drinks are also rarities in Boston Italian restaurants, but they’re key to the neighborhood vibe that Cinquecento’s striving for. I understand it can get pretty loud in there on weekend nights, but the bar staff are friendly, attentive, and willing to make a drink according to your preferences.
And it’s helpful if you prefer Negronis.
Address: 500 Harrison Avenue, Boston
Copyright © Boston BarHopper. All Rights Reserved.