A perfect Italian weekend in NEW YORK CITY

This week we travel overseas to one of my favorite Italians: Olimpia Piccolo. Olimpia and I met during the time I lived in Rome, where she brought me to all her favorite places: Al Pompiere, Porta Portese, San Calisto, Ristorante Abruzzi, just to name a few, and many more little unknown spots. We shared many caffès, cocktails, supplì, meals, and beautiful moments together. And one thing I know for sure: this girl has an eye for beauty. She knows where to find the best and most authentic spots. Over a year ago she moved to NYC, so I thought it was about time for a little interview!

My name is Olimpia Piccolo, and I’m an Italian photographer and creative based in New York. I grew up in Rome and moved to the city a little over a year ago. My work sits somewhere between photography, design, and visual storytelling, so I tend to experience New York through details—beautiful storefronts, interesting interiors, bookstores, flea markets, and long walks with my camera. What I love most about New York is that it constantly surprises me. You can leave home without a plan and still end up discovering something memorable.

Saturday

My ideal Saturday starts downtown with friends, usually in the West Village. If we can grab one of the outdoor tables at Commerce Inn, that’s where you’ll find us. It feels like a little escape from the city while still being right in the middle of it. The food is comforting, the people-watching is excellent, and there’s something about sitting outside on a sunny morning that makes the entire weekend feel full of possibility.

After brunch, we usually wander west toward the Hudson River. One of my favorite things about New York is that you can spend an entire afternoon simply walking. We’ll stroll along the West Side Highway, stop at Little Island, occasionally visit the Whitney Museum, or pop into a few galleries nearby. Sometimes we’ll sit by the water and talk for hours, other times we’ll follow whatever catches our attention. The city rewards curiosity.

As the afternoon turns into evening, I like to stop at Drift In. It’s one of my favorite places to catch the sunset on the West Side. I’ll order either a martini or an Aperol Spritz and sit outside watching the light change over the Hudson. Growing up in Italy, aperitivo was always about creating a pause in the day rather than rushing to the next thing, and Drift In captures that feeling surprisingly well. It’s one of those places where an hour disappears without you noticing.

From there, I head back uptown for one of my favorite New York rituals. Some weekends start with a comedy show on the Upper East Side, but they almost always end at Brandy’s Piano Bar. It’s one of those wonderfully unpretentious places where strangers become friends for a few hours. I order a Red Ruby Cosmopolitan—the best cosmopolitan I’ve had in the city—and sing along with everyone else. If you’re lucky, Maria, the legendary bartender, will leave her bartending duties and come over to sing some of her staple songs. It’s impossible to leave without a smile.

Sunday

Sundays are completely different. They’re slower, quieter, and usually reserved for myself. I love taking myself out on solo dates.

I start the morning at home making pancakes with side of bacon and eggs and taking my time with breakfast. New York moves fast during the week, so I like Sundays to feel intentionally unproductive.

From there, I head downtown to the Chelsea Flea Market. Even if I don’t buy anything, I love wandering through the stalls looking for unusual objects, old photographs, vintage frames, and pieces with a story behind them. Growing up around antiques has made me endlessly curious about the lives objects have lived before finding their way here

After the flea market, I’ll usually stop into a few thrift stores nearby—often the Goodwill around the corner—before making my way to Rizzoli Bookstore. It’s one of the most beautiful bookstores in the city and a place where I can easily lose an hour or two browsing through photography, art, and design books.

Before leaving the neighborhood, I like to stop at Eataly for an espresso and a fresh cannolo. It’s a small ritual, but one that instantly makes me feel connected to home.

My perfect Sunday afternoon is surprisingly simple: finding a chair in Madison Square Park, sitting in the sun with a book, and looking up at the Flatiron Building. I spend hours reading, people-watching, sketching, and letting the city move around me. As someone who grew up in Rome, I think both cities share an appreciation for slowing down and observing life. Some of my favorite New York moments happen when I’m not trying to get anywhere at all

By the time the sun starts setting, I feel reset and ready for another week.

My Go-To Spots

Brandy’s Piano Bar is the place I return to whenever I want a reminder of why I love New York. It feels welcoming, spontaneous, and full of characters.

Drift In is my favorite spot for a sunset aperitivo by the river.

Rizzoli is my favorite bookstore in the city—not just for the books, but for the atmosphere.

The Chelsea Flea Market is one of the few places where I can completely lose track of time.

And if I had to choose one ritual that makes a weekend feel complete, it would be sitting in the sun with a coffee and a book, whether that’s in Madison Square Park, by the Hudson River, in Central Park, or on a random bench I happen to discover while wandering. I almost always carry a sketchbook or camera with me. Even after a year in New York, I still treat the city as something I’m learning to look at.