It'll be early on. You'll round a corner on a beach road, maybe in Sconset or Aquinnah. And it will hit you. The quiet. The open Atlantic pulsing on the shore. Seabirds above and a breeze fanning the dunes. You'll imagine selling your possessions and buying a lobster boat. It's ok, the urge passes eventually. But you'll have five days to enjoy it.
1-2 Downshift into easygoing island life on Nantucket A gentle ride to Cisco Beach leads past beautiful 18th- and 19th-century sea captains' homes and lighthouses Circle the island on two wheels, with gardens, cranberry bogs, harbors, dunes and houses—sporting every shade of gray—enlivening your route The Nantucket Shipwreck and Lifesaving Museum chronicles the area's maritime heritage Up for a stroll along the Atlantic? Siasconset and Surfside beaches beckon with pristine stretches of sand.
3 Soak up the rich history of Nantucket Town on a walking tour A private boat transports us to Martha's Vineyard, simply called The Vineyard by locals Pedal a bike path to Edgartown, known for spectacular Greek Revival, Federal and Victorian architecture Ride out to Katama Beach past beautiful homes tucked among pines along a stretch of unspoiled beach popular with local kite-surfers.
4 Spin inland through forests and open meadows Fond of art? Galleries tempt you off your bike with watercolors, photography and sculptures by local and world-renowned artists Explore Chappaquiddick and the Cape Poge lighthouse—its first keeper in 1801 was appointed by Thomas Jefferson.
5 Ocean views and breezes abound on our ride out to Vineyard Haven, with its large estates overlooking Nantucket Sound Explore the unique town of Oak Bluffs, home to gingerbread cottages that were once part of a historic Methodist camp Enjoy a farewell lunch at the popular Black Dog Tavern.