Today, you’re 21. And you want to celebrate. So, you decide to round up your friends or maybe a love interest for your first legal night out. You’re thinking calm and classy—you want to get drunk, but with good food, drinks, and ambience.

For dinner, decide on Porta, a new Neapolitan place renowned for its wood–fired pizzas and cocktails. After that, drinks at 1 Tippling Place for craft cocktails and vintage decor. Then,  maybe you’ll try to sneak into a speakeasy like the Ranstead Room across the street. 

If you’re with friends, weave through the bustle of Porta to snag one of the long wooden bench tables sprinkled with tea lights, where Edison bulb string lights sway overhead and floor–to–ceiling mirrors lean against exposed brick.

If you’re with a date, find the mezzanine table for two with the best view of the marble bar and wood–fire oven below.

Either way, you’ll find yourself drawn into people–watching. It’s a Friday, and twentysomethings with loosened ties chatter at the bar, humming with energy and alcohol. Woodsmoke perfumes the air. Exchange glances with a couple of good–looking strangers and buzz with the awareness that people–watching goes both ways. 

Photo: Dayz Terry

The restaurant, occupying the cavernous yet cordoned–off space that it does, feels a little like the way Daisy described Gatsby’s parties—to paraphrase, they’re all the more intimate for being so large.

The waitress comes with smiles and menus. Linger on the cocktails, because you’re facing the most important question of the night: what to (legally) drink first? 

Perhaps Frabasile, which comes in a coupe glass, the kind they served champagne in before flutes came into fashion. Pale liquid, the tint of lemonade, swells in the shallow roundness, and a large basil leaf drapes across its surface. You take your first sip: sweet basil morphs slowly into tart lemon, all of it underscored by the kick of vodka. 

Or maybe you try the Venetian Spritz, whose three classic ingredients—Aperol, prosecco, and soda water—come together in a decadent, iced amber cocktail, redolent of the canals and nooks of Venice.

To eat, start off with a dish of pan–roasted octopus, fingerling potatoes, and fennel, and another dish of goat’s milk ricotta, roasted grapes, and charred bread. The octopus tentacles come whole, crisp, and purplish–red, suction cups beckoning. The meat is chewy and succulent. Your less adventurous friends may not be as excited about this dish, but it’s one of the most popular ones, the waitress assures them.

While you wait for your next courses, order your second cocktail (it is your birthday, after all). If you’re a whiskey person, try the Old Blue (which is actually pink). With its mix of bourbon, lemon, vanilla, and blueberry, it has the punch of a whiskey sour, “but crazy,” as one of your friends eloquently puts it. It comes with three plump blueberries skewered like olives and a sprig of mint. 

You might also consider Horse of a Different Color, a cocktail bright in both color and taste. The sharpness of Campari (from which the drink gets its vibrant orange hue), the sweetness of lime juice, and the herby bitterness of Fernet clash in the most fortuitous of ways. Ginger beer adds a bubbly undertone to the mixture.

Photo: Dayz Terry

Indulge yourself and order the Delano, a dish of stout–braised short rib on a bed of pillowy polenta. The tender meat falls off the bone  and is garnished with cipollini onions, braised in balsamic, and oil.

Finally, the pizza. “Is pizza classy?” someone hesitatingly asks. “If it’s wood–fired, yeah,” another answers with authority. The debate is settled, and your pie arrives, sweltering with melting cheese and brick oven heat. The pizza is glistening with tomato and soppressata, their deep reds broken up by the brilliant whites of ricotta and mozzarella–both housemade.

Take a bite. It transports you. Let sauce dribble down your chin as you eat because the pizza is so good you’ve forgotten you wanted this to be a classy night. Even those few unholies out there who don’t like to eat the crust will be defied by this one, which toes the line between chewy and crispy, reaching new gastronomical heights. 

Now, dessert. The panettone sticky toffee pudding, a glorious melding of a beloved Italian pastry, reserved for celebrations, and a diabetes–inducing British dessert, is a must. The pudding comes in a small pool of date caramel, with which it is also soaked, and dolloped with cream. It melts in your mouth in the most literal and least figurative possible sense of that overused phrase. 

After dinner, it’s time to continue the revelry. Head to 1 Tippling Place, a little bar squeezed between two buildings off 20th and Chestnut, so hidden that you accidentally walk past it the first time. But then you see the discreet dark blue plaque on the wall outside with “1 Tippling Place” on it like a street sign.

Through green–paneled windows you can make out plush armchairs and framed oil paintings bathed in warm yellow lamplight. Spotting the cute bartender, take a seat on one of the wooden barstools. He pours you water and hands you drink menus. 

Peruse the list of craft cocktails with ingredients like brown butter washed gin and fig jam, and gape at the gleaming collection of bottles—a lot of whiskey—in the shelves in front of you. Settle on the Tatanka, a cozy mix of vodka, apple cider, and apple bitters, with dashes of lemon and nutmeg. Chat with the bartender, the warmth of the drink washing over you. 

After 1 Tippling Place, try to sneak your way into the Ranstead Room, the speakeasy across the street. Weave through a back alley to find the hidden bar, put your name on the list, and hope for the best. Head back to the first bar while you wait for a phone call from the speakeasy letting you know a table’s opened up for your party. Don’t worry, they’ll call. It is your birthday, after all. 

TL;DR: Planning your first (legal) night out: Porta for dinner, 1 Tippling Place for drinks. 


Porta: 1216 Chestnut Street
1 Tippling Place: 2006 Chestnut Street
Ranstead Room: 2013 Ranstead Street

Price Range: $$$–$$$$