Romantic anniversary

The Hamptons institution. Wood-fired everything, garden vegetables, and a guest list that spans presidents to publishers.

Time-warp Main Street classic with one of the deepest wine lists on the East Coast. Also a hotel (8 rooms) and late-night bar.

Best sunset deck in Sag Harbor. Book the early seating, order oysters.

Inn dining room with crackling fireplace and one of the best off-season tables on the East End.

Jean-Georges' farm-driven Bridgehampton flagship inside a restored 1842 mansion. Breakfast daily 8–10:30am, lunch weekdays noon–3pm, weekend brunch 11:30am–3pm, dinner daily 5:30–9pm.

Pierre Weber's village-center bistro. Steak frites, escargot, bonjour Madame.

Western-edge French-Med fine dining. The off-season escape worth the drive.

North Fork's tasting-menu temple. Yes, it's worth the bridge.

Sean MacPherson's lakeside Mediterranean. Best sunset in Montauk, full stop.

Since 1973. Red sauce, Chianti bottles on the walls, and the sweetest year-round date night in Sag.

Fresno's Michael Nolan came home to the Main Street he grew up on: a dark, candlelit room of leather banquettes that feels like an English pub washed ashore. Updated American classics from the Fresno kitchen team; locals order the striped bass.

Balinese instincts layered over French technique, built on East End produce and Montauk seafood, from the Roundtree's Bali-inspired kitchen. The bar program comes from Martiny's alum Takuma Watanabe. Ask for the garden.

The Pridwin's water-view restaurant and bar above Crescent Beach: daily lunch, dinner every night, and a terrace built for sunset.