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 Sample local microbrews, wine and even vodka during lunch at Cisco Brewery 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. 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 Ride out to Katama Beach past beautiful homes tucked among pines and scrub oak along a stretch of unspoiled beach popular with local kite-surfers Pedal a bike path to Edgartown, known for spectacular Greek Revival, Federal and Victorian architecture Explore the unique town of Oak Bluffs, home to gingerbread cottages that were once part of a historic Methodist camp. DAY 4 The red-clay cliffs of Aquinnah, with a 200-year-old lighthouse 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 the Cape Poge lighthouse – its first keeper in 1801 was appointed by Thomas Jefferson. DAY 5 Exhilarating ocean views and breezes abound on our ride out to Vineyard Haven and Tisbury, with its large estates overlooking Nantucket Sound and the islands only year-round port Enjoy lunch at the ever-popular Black Dog Tavern.

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