Itinerary

Days 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 - gardens, cranberry bogs, harbors and dunes enliven 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.

Day 3 Edgartown's Colonial roots and art galleries  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 Stroll through historic Oak Bluffs, a chic stop for shoppers  Pedal a bike path to Edgartown, known for spectacular Greek Revival, Federal and Victorian architecture.

Day 4 The red-clay cliffs of Aquinnah, with a 200-year-old lighthouse  Spin inland through forests and open meadows, past houses sporting every shade of gray Fond of art? Galleries tempt you off your bike with watercolors, photography and sculptures by local and world-renowned artists Explore the Cape Poge lighthouse - its first keeper in 1801 was appointed by Thomas Jefferson.

Day 5 Exhilarating ocean views and breezes  Ride to Vineyard Haven for lunch at the ever-popular Black Dog Tavern  Ferry across Nantucket Sound to Woods Hole.

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