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 and dunes enlivening your route • Refresh yourself at a favorite local watering spot offering much-loved microbrews and wines • Take a fascinating look at the island’s maritime history at the Nantucket Shipwreck and Lifesaving Museum, which exhibits original boats, relics of the island’s legendary shipwrecks and photographs of thrilling sea rescues • Spin past old barns, osprey nests, island grasses and fields of wildflowers 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 • Take in the fresh sea breeze and ocean views on the way to Katama Beach • E-bike to the port town of Vineyard Haven, cruising by stately homes on the West Chop peninsula • 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 Katama Beach • Pass through the Great Plains of Martha’s Vineyard before a farewell lunch.