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 island life on Nantucket | A gentle ride to Cisco Beach leads past 18th- and 19th-century sea captains’ homes and lighthouses | Explore the island by bike, with gardens, cranberry bogs, harbors, dunes and houses—sporting every shade of gray—enlivening your route | The Nantucket Shipwreck & 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 | Pedal a bike path to Edgartown, known for amazing 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, overlooking Nantucket Sound | Explore the unique town of Oak Bluffs, home to historic gingerbread cottages | Enjoy a farewell lunch at the popular Black Dog Tavern.