Lunches of Legend

Sip away an afternoon over one of the city’s most storied traditions: the Three-Martini Lunch

For certain high-power Manhattanites, the most important meal of the day is neither breakfast nor dinner, but rather lunch—the Three Martini Lunch, to be exact. It’s no secret that more business deals are made over these long, alcohol-infused meals than in any meeting room, despite their leisurely appearance. But just because you’re coming from the office doesn’t mean you can’t partake in the practice, so pull up a chair at one of these restaurants and soak in the city’s most storied meal.

With the opening of One World Trade Center, the gorgeous new Fulton Center subway station, and a host of new shops and hotels in the works, Manhattan’s financial district is reclaiming its days as one of the city’s most glamorous neighborhoods. On Wall Street, Cipriani Club 55 is a large contributor to the district’s glitter, where businessmen and the occasional celebrity come to sit in the chandeliered dining room or out on the pillared balcony for a lunch that may roll into a couple hours or more. Ingredients imported from the boot beautifully uphold Cipriani’s reputation for fantastic Italian food, best complimented by the restaurant’s dry martinis, whose recipe comes from Cipriani’s parent restaurant, Harry’s Bar in Venice. Founder Giuseppe Cipriani is also hailed as being the inventor of the Bellini, and it’s all but requisite to start or end a meal with a flute of Prosecco and white peach juice. (Wall St. nr. Hanover St.)

If objects could speak, the banquettes in the Grill Room at the Four Seasons Restaurant would probably have more insider information to tell about big business and high society than all the city’s newspapers put together. Manhattan’s most influential circles have been reserving them for their afternoon tête-à-têtes since the restaurant opened in 1959, taking down local oysters in the French walnut–paneled dining room, or perhaps nibbling on the restaurant’s cultish crab cakes in the serene Pool Room, whose cerulean centerpiece pool is surrounded by trees that change seasonally, along with the menus. The wine list here is renowned, but in daylight hours, go for the cocktail menu, comprised of all the classics executed to perfection—perfect accompaniments for having a prolonged power lunch of your own. (52nd St. nr. Park Ave.)

When it comes to wall art, few restaurants in the world can hold a flame to that of The Palm. Back in the 1920s and 30s when it first opened, the artists, writers, and intellects who dined here but couldn’t foot their bill paid instead by drawing portraits and caricatures on the walls, and few things make for better table conversation than ordering a round of drinks and letting their coquettishness set the tone for a relaxed afternoon. For lunch, a three-course set power lunch, some specialty burgers, and a selection from the dinner menu are served in famously generous portions, making for languid meals that call for second and third rounds to wash them down. (Second Ave. at 45th St.)

Since 1977, the green-and-white façade of Smith & Wollensky has stood as an unmistakable harbinger for some of the most prime meats in the city. Its loyal lunchtime clientele attests to the fact that few other places offer a lunchtime selection of filets as extensive as here—rubbed with coffee and cocoa, crusted with gorgonzola, au poivre—in addition to rib eyes, chops, salads, and seafood. And while its wine selection has repeatedly won awards from Wine Spectator magazine, the two signature martinis are perfect for midday unwinds: Charlie Smith’s “Ultimat” Martini with Marcona almond-stuffed olives, and Ralph Wollensky’s decadent “Signature” Martini with black peppercorns and 24-karat gold flakes. (Third Ave. at 50th St.)