Martha's Vineyard

Martha's Vineyard is not just one destination but many, so varied are the communities that inhabit this 100-square-mile mini-continent a mere 7 miles off Cape Cod. Amid the farms tucked inland in Chilmark, you could easily imagine yourself transplanted to post-hippie Vermont. Along the coast, workaday Vineyard Haven boasts its share of chichi shops; spirited Oak Bluffs, which morphed from an 1830s Methodist encampment (tents inspired the gaudily-painted carpenter's-gothic cottages), can boast a proud history as the "black Newport"; buttoned-down Edgartown harbors captains of industry in lieu of the prosperous whalers of old; Chappaquidick, ...

Martha's Vineyard is not just one destination but many, so varied are the communities that inhabit this 100-square-mile mini-continent a mere 7 miles off Cape Cod. Amid the farms tucked inland in Chilmark, you could easily imagine yourself transplanted to post-hippie Vermont. Along the coast, workaday Vineyard Haven boasts its share of chichi shops; spirited Oak Bluffs, which morphed from an 1830s Methodist encampment (tents inspired the gaudily-painted carpenter's-gothic cottages), can boast a proud history as the "black Newport"; buttoned-down Edgartown harbors captains of industry in lieu of the prosperous whalers of old; Chappaquidick, an unspoiled preserve, is a five-minute hop by ferry; the Wampanoag tribe have reclaimed the magnificent Aquinnah bluffs; and Menemsha remains a bustling fishing port, instantly recognizable as the setting for Jaws. With a few roomy exceptions (e.g., South Beach), most sand access is private, so you'll need to know someone or stay at a nice inn with privileges to get within nipping distance. Just kidding! So far, man-eating sharks remain fictional, whereas the pleasures of this island playground are immediate and real.

About the Expert

Sandy MacDonald has written guidebooks to Cape Cod and Boston for Frommer's, Access and Globe-Pequot, and for many years has covered Nantucket for Fodor's.