NYC to North Fork: about 105 miles
Why go: For a laid-back alternative to the glamorous Hamptons, the North Fork of Long Island features white-clapboard houses and farm stands, along with some of the region's top wineries. Bedell Cellars is widely acknowledged as the benchmark of Long Island Merlots, and Peconic Bay Winery produces terrific Rieslings.
Where to stop: The Shinn Estate Farmhouse is run by former Manhattan restaurateurs David Page and Barbara Shinn on their Long Island vineyard (Double from $149 to $169).
What to eat along the way: The seafood dishes are excellent at Vine Street Café, a white-shingled restaurant on Shelter Island run by two Union Square Café alums.