Chef Laura Pensiero opened Gigi Trattoria in 2001 with her then-husband, a New York City chef. Within two years, she’d bought him out, thinking her involvement would be temporary. Instead, as the restaurant approaches its 25th anniversary next year, she’s spent more than two decades transforming from Type-A perfectionist to collaborative matriarch, surrounding herself with people like general manager Jean-Luc and husband Cornelius and an evolving staff of locals. 

“I’ve seen children grow up at Gigi’s,” Pensiero says. “Some of the people I employed as young adults and teenagers are having kids, and they’re bringing their kids in. I feel Gigi’s is an organism. It’s my post-grad college kid at this point.”

Pensiero’s background in nutrition and public health—including working with Memorial Sloan Kettering and consulting on food and healthcare in New York City—shaped her culinary approach. The menu and technique skew Mediterranean: fresh ingredients and balanced flavors, with minimal intervention.

That sense of continuity and growth extends to every plate that leaves the kitchen. The gambas garlicky paprika shrimp swimming in fragrant juices arrives with wedges of fresh bread for mopping up every last drop ($19). The bread matters here: crusty enough to hold its structure when dragged through the liquid at the bottom of the bowl, soft enough to soak up every bit of that deliciously spicy infused sauce. This is the kind of dish that creates a lull in the conversation as diners dive in. The shrimp are perfectly cooked, the sauce a masterclass in balancing heat against richness, garlic against the sweet brine of the seafood. It’s rustic and refined simultaneously, the sort of preparation that looks simple but requires years to perfect.

Appetizers range from meatballs, burrata, calamari, or fried oysters to sumptuous lamb skewers, saffron aroncino, cheeses and salumi, or a trio of hummus ($16-$24). Side dishes work just as well as heavier appetizers, from creamy gigantes white Tuscan beans to parmesan dusted Brussels sprouts ($12-$16).

Gigi’s interior is always buzzing with patrons.

Then there are the Tuscan fries—yes, fries—but elevated to something unexpected. Whether you order them plain, dusted in parmesan, or drizzled in truffle oil, they arrive sizzling hot with a fresh branch of sage tucked among them, its leaves wilting from the heat, releasing an aroma that brings the garden indoors ($12). You can taste it in the air before the first bite. It’s a small touch that reveals a central understanding: great cooking engages all the senses, and sometimes the best magic happens in the simplest preparations.

The menu demonstrates remarkable range, touching all shores of the Mediterranean Sea, with dishes from Spain, Italy, and Greece. At Gigi, all the pastas are made in-house. Orecchiette arrives in vibrant red pepper pesto, studded with Meiller Farm pork sausage and bitter broccoli rabe, finished with grana padano—a study in balancing richness against brightness ($29). The sauces taste like mom’s cooking, simmering from the stove. Sicilian cauliflower becomes an event: roasted until caramelized, it’s punctuated by briny green olives and capers, sweetened with sultanas, finished with herbed gremolata ($15). The lobster ravioli showcases pasta-making skill and restraint, letting quality ingredients speak without an excess of embellishment ($33).

Tagliatelle bolognese

Other mains that tempt guests to return again and again include traditionals like lasagna bolognese, penne arrabbiato, prosciutto-wrapped filet mignon, rib-eyes and burgers. Main dishes range from $22 to $36, with the rib-eye serving parties of 3-4 for $110. The flatbread pizzas, AKA skizzas, are an afforadable dining option with standout options like Rustica with ricotta-roasted garlic spread, sausage, broccoli rabe, shaved parmesan, and chili flakes; or the sweet-and-savory Bianca with rosemary fig jam, pear, arugula, goat cheese, and truffle oil (both $20).

With a full bar ready to serve complements to every course and dish, the impressive wine list centers European offerings ranging from Albariño to Chateauneuf du Pape ($41-70 a bottle) up to a 2018 Sassicaia ($480) for special celebrations. Cocktails ($14), draft and bottle beers, and ciders are also available, highlighting Hudson Valley brewing and fermentation expertise. 

It’s impossible to resist the dessert menu. The tiramisu—light and fluffy, tastes like fresh cream from a country kitchen, inspiring the feeling of being transported to your grandmother’s table, or to Italy itself ($11). Dulces from biscotti to affogatto and seasonal favorites like rustic apple tart and sweet potato maple cheesecake satisfy the sweet tooth ($7-13).

Cranberry jalapeño margarita

Perhaps most telling is the hospitality itself. When a guest requests something off-menu—a sake martini ($14) made with premium Dassai (a dietary modification), the staff finds a way to make it work. When ordering Faroe Island Salmon, the server asks how you’d like it cooked, a question so rare it surprises ($34). This flexibility isn’t accidental. It flows from Pensiero’s leadership: trust your team, empower them to adapt, treat every guest like they matter.

“You have to change; you’re not going to be relevant if you don’t change at all—you keep what works, and you keep moving forward,” Pensiero explains. “But if you can bring a consistent, good product, even if the product changes—that’s really the key to success.”

That philosophy explains how Gigi’s has thrived in the center of Rhinebeck, becoming the kind of place where celebrations happen across generations.

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Written by
Susan Brearly