This island 30 miles off the coast of Cape Cod, Massachusetts, was settled by Quakers in the 17th century, and became the capital of the American whaling industry in the 18th century. Dubbed the "Grey Lady" because it's often covered in a blanket of fog, Nantucket's windswept moors, rugged beaches, and rose-covered trellises are quintessential New England. This is the ideal spot for a romantic and low-key getaway.
Before You Go: Need-to-know info
Travel time: 3 hours from NYC, 8 hours from LA
Getting around: Bikes, seasonal shuttle bus (June to September), island ferry (for visits to nearby Martha's Vineyard). Note: It's expensive to bring a car onto the island. Most people park in Hyannis, Massachusetts, and catch a ferry ride over.
When To Go: Nantucket at its best
Best weather: June to September
Best prices: Early spring, late fall, and winter (if open). Call ahead if traveling during low season to make sure activities you're interested in will be up and running.
History: You can feel Nantucket's nautical history with every step you take along its cobblestone streets. Strict building codes keep all houses draped in weathered gray shingles, and many of them still bear walkways along the roof to enable the swift dousing of chimney fires. These roof walks were also called "widow's walks" because this is where lonely wives were said to pace night after night hoping for a glimpse of their husband's ship.
Whaling: Take in a bit of Nantucket's proud past -- including the skeleton of a 40-foot whale -- at the Whaling Museum and the Peter Foulger Museum. Then witness the real thing on a Whale and Seabird Cruise led by Nantucket Whale watch.
Beaches: For waves, go to the Atlantic side; for gentle surf, try Nantucket Sound. Either way the sand will be clean and the air breezy.
Nature tours: Spread your wings with hawks, falcons, and gulls on a tour of the nature preserve at the northeastern end of the island with Great Point Tours.
Quaint city strolls: Browse shops selling scrimshaw (an art form originally used by American whalers to carve and engrave whale ivory), handmade quilts, model ships, jewelry, and antiques on Main Street, or visit the painting and sculpture galleries of Old South Wharf.