North Fork, New York
A sprawling 19th-century home on Peconic Bay with formal gardens and a private beach and dock, Harbor Knoll is picture perfect. The B&B with four rooms plus freestanding cottage is a short walk to the center of Greenport. But with a Prohibition-era bar and harbor views everywhere you turn, it's hard to imagine you'll ever want to leave; 631/477-2352.
Eat: Munch on crab cakes and fried chicken for lunch at F.O.B. (Frisky Oyster Bar). It will be hard to resist the tasting menu at The North Fork Table and Inn that might include roasted baby beets with local goat cheese, pan-roasted Long Island duck breast, and a chocolate-caramel tart or upside-down caramelized apple tart.
Do: Stop by the White Flower Farm House for vintage French linens, rustic garden furniture, or anything else you need to create the urban-meets-country style of North Fork. Make sure you pick up a map of area wineries at the Long Island Wine Council. You won't want to miss the oldest winery in the area, Castello di Borghese.