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 charming cottages, cranberry bogs, harbors and dunes enlivening your route • Refresh yourself at a favorite local brewery • Take a fascinating look at the island’s maritime history at the Nantucket Shipwreck & Lifesaving Museum, which exhibits original boats, relics of the island’s legendary shipwrecks and photographs of thrilling sea rescues • Spin past pitch pines, osprey nests, hydrangeas and island grasses to Madaket Beach, the landing site of the first European settlers • Up for a stroll along the Atlantic? Siasconset and Surfside Beaches beckon with pristine stretches of sand.

Soak up the rich history of Nantucket Town on a walking tour • A ferry transports us to Martha’s Vineyard • Explore the unique town of Oak Bluffs, home to colorful gingerbread cottages • Pedal past stately homes on East Chop peninsula and take in ocean views from Martha’s Vineyard • Arrive in Edgartown, known for amazing Greek Revival, Federal and Victorian architecture • Cycle 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 • Take in the exhilarating sea air and more spectacular ocean views on your ride to the quieter, rural west side of the island • Pass through Katama Plains on the south side of Martha’s Vineyard before a farewell lunch.