Nantucket
Prep talk: going native on Nantucket.

From the March 24, 2003 Issue of New York

Quiet and conservative Nantucket has preppy charm to spare. Every home seems perfectly weathered by the salt air. The lush green lawns are manicured, the wicker furniture is white. Even the local food—boiled lobster with fries and beer—speaks of understated sophistication (of course, it has to be the right beer; local microbrew Whale’s Tale Pale Ale is the way to go). The main part of town is marked by cobblestone streets and shops filled with early-American antiques, housewares, silver—you know, Waspy stuff. To make like a local, don your best Lilly Pulitzer, loafers, and linen and head to the Hub for your morning paper and coffee, then sit outside on a bench and feign indifference. Later, rent a bike from Young’s Bicycle Shop and tool around the bike paths. Stay at the breezy White Elephant Hotel, just a five-minute walk to the historic downtown area. Many rooms have working fireplaces and views of the sea. Watch the sun set over the harbor and the lighthouse lights spin. The hotel also has croquet and boccie gear. Preppy indeed.

-- Tara Mandy